id	sid	tid	token	lemma	pos
eurjchem-1645	1	1	untitled	untitle	VERB
eurjchem-1645	1	2	european	european	PROPN
eurjchem-1645	1	3	journal	journal	PROPN
eurjchem-1645	1	4	of	of	ADP
eurjchem-1645	1	5	chemistry	chemistry	NOUN
eurjchem-1645	1	6	8	8	NUM
eurjchem-1645	1	7	(	(	PUNCT
eurjchem-1645	1	8	4	4	NUM
eurjchem-1645	1	9	)	)	PUNCT
eurjchem-1645	1	10	(	(	PUNCT
eurjchem-1645	1	11	2017	2017	NUM
eurjchem-1645	1	12	)	)	PUNCT
eurjchem-1645	1	13	400‐409	400‐409	NUM
eurjchem-1645	1	14	european	european	ADJ
eurjchem-1645	1	15	journal	journal	PROPN
eurjchem-1645	1	16	of	of	ADP
eurjchem-1645	1	17	chemistry	chemistry	NOUN
eurjchem-1645	1	18	issn	issn	PROPN
eurjchem-1645	1	19	2153‐2249	2153‐2249	PROPN
eurjchem-1645	1	20	(	(	PUNCT
eurjchem-1645	1	21	print	print	NOUN
eurjchem-1645	1	22	)	)	PUNCT
eurjchem-1645	1	23	/	/	SYM
eurjchem-1645	1	24	issn	issn	PROPN
eurjchem-1645	1	25	2153‐2257	2153‐2257	NUM
eurjchem-1645	1	26	(	(	PUNCT
eurjchem-1645	1	27	online	online	ADJ
eurjchem-1645	1	28	)	)	PUNCT
eurjchem-1645	1	29			NOUN
eurjchem-1645	1	30	2017	2017	NUM
eurjchem-1645	1	31	atlanta	atlanta	PROPN
eurjchem-1645	1	32	publishing	publishing	PROPN
eurjchem-1645	1	33	house	house	PROPN
eurjchem-1645	1	34	llc	llc	PROPN
eurjchem-1645	1	35	‐	‐	PUNCT
eurjchem-1645	1	36	all	all	DET
eurjchem-1645	1	37	rights	right	NOUN
eurjchem-1645	1	38	reserved	reserve	VERB
eurjchem-1645	1	39	‐	‐	NOUN
eurjchem-1645	1	40	printed	print	VERB
eurjchem-1645	1	41	in	in	ADP
eurjchem-1645	1	42	the	the	DET
eurjchem-1645	1	43	usa	usa	PROPN
eurjchem-1645	1	44	http://dx.doi.org/10.5155/eurjchem.8.4.400-409.1645	http://dx.doi.org/10.5155/eurjchem.8.4.400-409.1645	PROPN
eurjchem-1645	1	45	european	european	PROPN
eurjchem-1645	1	46	journal	journal	PROPN
eurjchem-1645	1	47	of	of	ADP
eurjchem-1645	1	48	chemistry	chemistry	PROPN
eurjchem-1645	1	49	journal	journal	PROPN
eurjchem-1645	1	50	webpage	webpage	NOUN
eurjchem-1645	1	51	:	:	PUNCT
eurjchem-1645	1	52	www.eurjchem.com	www.eurjchem.com	X
eurjchem-1645	1	53	synthesis	synthesis	NOUN
eurjchem-1645	1	54	and	and	CCONJ
eurjchem-1645	1	55	antiproliferative	antiproliferative	ADJ
eurjchem-1645	1	56	activity	activity	NOUN
eurjchem-1645	1	57	of	of	ADP
eurjchem-1645	1	58	3‐(substituted)‐4,5,6,7‐tetrahydro‐6‐	3‐(substituted)‐4,5,6,7‐tetrahydro‐6‐	NUM
eurjchem-1645	1	59	(	(	PUNCT
eurjchem-1645	1	60	substituted)‐1h‐pyrazolo[3,4‐c]pyridine	substituted)‐1h‐pyrazolo[3,4‐c]pyridine	NOUN
eurjchem-1645	1	61	derivatives	derivative	NOUN
eurjchem-1645	1	62	chandrakant	chandrakant	VERB
eurjchem-1645	1	63	pawar	pawar	PROPN
eurjchem-1645	1	64	1	1	NUM
eurjchem-1645	1	65	,	,	PUNCT
eurjchem-1645	1	66	*	*	PUNCT
eurjchem-1645	1	67	,	,	PUNCT
eurjchem-1645	1	68	dattatraya	dattatraya	NOUN
eurjchem-1645	1	69	pansare	pansare	NOUN
eurjchem-1645	1	70	2	2	NUM
eurjchem-1645	1	71	and	and	CCONJ
eurjchem-1645	1	72	devanand	devanand	NOUN
eurjchem-1645	1	73	shinde	shinde	NOUN
eurjchem-1645	1	74	3	3	NUM
eurjchem-1645	1	75	1	1	NUM
eurjchem-1645	1	76	department	department	NOUN
eurjchem-1645	1	77	of	of	ADP
eurjchem-1645	1	78	chemical	chemical	PROPN
eurjchem-1645	1	79	technology	technology	PROPN
eurjchem-1645	1	80	,	,	PUNCT
eurjchem-1645	1	81	dr	dr	PROPN
eurjchem-1645	1	82	.	.	PROPN
eurjchem-1645	1	83	babasaheb	babasaheb	PROPN
eurjchem-1645	1	84	ambedkar	ambedkar	PROPN
eurjchem-1645	1	85	marathwada	marathwada	PROPN
eurjchem-1645	1	86	university	university	PROPN
eurjchem-1645	1	87	,	,	PUNCT
eurjchem-1645	1	88	aurangabad	aurangabad	PROPN
eurjchem-1645	1	89	,	,	PUNCT
eurjchem-1645	1	90	431004	431004	NUM
eurjchem-1645	1	91	,	,	PUNCT
eurjchem-1645	1	92	ms	ms	PROPN
eurjchem-1645	1	93	,	,	PUNCT
eurjchem-1645	1	94	india	india	PROPN
eurjchem-1645	1	95	2	2	NUM
eurjchem-1645	1	96	department	department	NOUN
eurjchem-1645	1	97	of	of	ADP
eurjchem-1645	1	98	chemistry	chemistry	NOUN
eurjchem-1645	1	99	,	,	PUNCT
eurjchem-1645	1	100	deogiri	deogiri	PROPN
eurjchem-1645	1	101	college	college	PROPN
eurjchem-1645	1	102	,	,	PUNCT
eurjchem-1645	1	103	aurangabad	aurangabad	PROPN
eurjchem-1645	1	104	,	,	PUNCT
eurjchem-1645	1	105	431005	431005	NUM
eurjchem-1645	1	106	,	,	PUNCT
eurjchem-1645	1	107	ms	ms	PROPN
eurjchem-1645	1	108	,	,	PUNCT
eurjchem-1645	1	109	india	india	PROPN
eurjchem-1645	1	110	3	3	PROPN
eurjchem-1645	1	111	department	department	NOUN
eurjchem-1645	1	112	of	of	ADP
eurjchem-1645	1	113	chemistry	chemistry	PROPN
eurjchem-1645	1	114	,	,	PUNCT
eurjchem-1645	1	115	shivaji	shivaji	PROPN
eurjchem-1645	1	116	university	university	PROPN
eurjchem-1645	1	117	,	,	PUNCT
eurjchem-1645	1	118	vidyanagar	vidyanagar	NOUN
eurjchem-1645	1	119	,	,	PUNCT
eurjchem-1645	1	120	kolhapur	kolhapur	PROPN
eurjchem-1645	1	121	,	,	PUNCT
eurjchem-1645	1	122	416004	416004	NUM
eurjchem-1645	1	123	,	,	PUNCT
eurjchem-1645	1	124	ms	ms	PROPN
eurjchem-1645	1	125	,	,	PUNCT
eurjchem-1645	1	126	india	india	PROPN
eurjchem-1645	1	127	*	*	PUNCT
eurjchem-1645	1	128	corresponding	correspond	VERB
eurjchem-1645	1	129	author	author	NOUN
eurjchem-1645	1	130	at	at	ADP
eurjchem-1645	1	131	:	:	PUNCT
eurjchem-1645	1	132	department	department	NOUN
eurjchem-1645	1	133	of	of	ADP
eurjchem-1645	1	134	chemical	chemical	PROPN
eurjchem-1645	1	135	technology	technology	PROPN
eurjchem-1645	1	136	,	,	PUNCT
eurjchem-1645	1	137	dr	dr	PROPN
eurjchem-1645	1	138	.	.	PROPN
eurjchem-1645	1	139	babasaheb	babasaheb	PROPN
eurjchem-1645	1	140	ambedkar	ambedkar	PROPN
eurjchem-1645	1	141	marathwada	marathwada	PROPN
eurjchem-1645	1	142	university	university	PROPN
eurjchem-1645	1	143	,	,	PUNCT
eurjchem-1645	1	144	aurangabad	aurangabad	PROPN
eurjchem-1645	1	145	,	,	PUNCT
eurjchem-1645	1	146	431004	431004	NUM
eurjchem-1645	1	147	,	,	PUNCT
eurjchem-1645	1	148	ms	ms	PROPN
eurjchem-1645	1	149	,	,	PUNCT
eurjchem-1645	1	150	india	india	PROPN
eurjchem-1645	1	151	.	.	PUNCT
eurjchem-1645	2	1	tel	tel	PROPN
eurjchem-1645	2	2	.	.	PUNCT
eurjchem-1645	2	3	:	:	PUNCT
eurjchem-1645	3	1	+91.0240.2403308	+91.0240.2403308	X
eurjchem-1645	3	2	.	.	PUNCT
eurjchem-1645	4	1	fax	fax	NOUN
eurjchem-1645	4	2	:	:	PUNCT
eurjchem-1645	4	3	+91.0240.2400413	+91.0240.2400413	X
eurjchem-1645	4	4	.	.	PUNCT
eurjchem-1645	4	5	e‐mail	e‐mail	PUNCT
eurjchem-1645	5	1	address	address	NOUN
eurjchem-1645	5	2	:	:	PUNCT
eurjchem-1645	5	3	dbschandrakant13@gmail.com	dbschandrakant13@gmail.com	PROPN
eurjchem-1645	5	4	(	(	PUNCT
eurjchem-1645	5	5	c.	c.	PROPN
eurjchem-1645	5	6	pawar	pawar	PROPN
eurjchem-1645	5	7	)	)	PUNCT
eurjchem-1645	5	8	.	.	PUNCT
eurjchem-1645	6	1	article	article	NOUN
eurjchem-1645	6	2	information	information	PROPN
eurjchem-1645	6	3	abstract	abstract	ADJ
eurjchem-1645	6	4	doi	doi	PROPN
eurjchem-1645	6	5	:	:	PUNCT
eurjchem-1645	6	6	 	 	SPACE
eurjchem-1645	6	7	10.5155	10.5155	NUM
eurjchem-1645	6	8	/	/	SYM
eurjchem-1645	6	9	eurjchem.8.4.400	eurjchem.8.4.400	ADP
eurjchem-1645	6	10	-	-	PUNCT
eurjchem-1645	6	11	409.1645	409.1645	NUM
eurjchem-1645	6	12	received	receive	VERB
eurjchem-1645	6	13	:	:	PUNCT
eurjchem-1645	6	14	30	30	NUM
eurjchem-1645	6	15	august	august	PROPN
eurjchem-1645	6	16	2017	2017	NUM
eurjchem-1645	6	17	received	receive	VERB
eurjchem-1645	6	18	in	in	ADP
eurjchem-1645	6	19	revised	revise	VERB
eurjchem-1645	6	20	form	form	NOUN
eurjchem-1645	6	21	:	:	PUNCT
eurjchem-1645	6	22	23	23	NUM
eurjchem-1645	6	23	september	september	PROPN
eurjchem-1645	6	24	2017	2017	NUM
eurjchem-1645	6	25	accepted	accept	VERB
eurjchem-1645	6	26	:	:	PUNCT
eurjchem-1645	6	27	23	23	NUM
eurjchem-1645	6	28	september	september	PROPN
eurjchem-1645	6	29	2017	2017	NUM
eurjchem-1645	6	30	published	publish	VERB
eurjchem-1645	6	31	online	online	ADV
eurjchem-1645	6	32	:	:	PUNCT
eurjchem-1645	6	33	31	31	NUM
eurjchem-1645	6	34	december	december	PROPN
eurjchem-1645	6	35	2017	2017	NUM
eurjchem-1645	6	36	printed	print	VERB
eurjchem-1645	6	37	:	:	PUNCT
eurjchem-1645	6	38	31	31	NUM
eurjchem-1645	6	39	december	december	PROPN
eurjchem-1645	6	40	2017	2017	NUM
eurjchem-1645	6	41	  	  	SPACE
eurjchem-1645	6	42	a	a	DET
eurjchem-1645	6	43	series	series	NOUN
eurjchem-1645	6	44	of	of	ADP
eurjchem-1645	6	45	new	new	ADJ
eurjchem-1645	6	46	molecules	molecule	NOUN
eurjchem-1645	6	47	having	have	VERB
eurjchem-1645	6	48	3‐(substituted)‐4,5,6,7‐tetrahydro‐6‐(substituted)‐1h‐	3‐(substituted)‐4,5,6,7‐tetrahydro‐6‐(substituted)‐1h‐	NUM
eurjchem-1645	6	49	pyrazolo[3,4‐c]pyridine	pyrazolo[3,4‐c]pyridine	NOUN
eurjchem-1645	6	50	and	and	CCONJ
eurjchem-1645	6	51	3‐(substituted)‐5,6‐dihydro‐6‐(substituted)‐1h‐pyrazolo[3,4‐c	3‐(substituted)‐5,6‐dihydro‐6‐(substituted)‐1h‐pyrazolo[3,4‐c	NUM
eurjchem-1645	6	52	]	]	X
eurjchem-1645	6	53	pyridin‐7(4h)‐one	pyridin‐7(4h)‐one	NOUN
eurjchem-1645	6	54	derivatives	derivative	NOUN
eurjchem-1645	6	55	were	be	AUX
eurjchem-1645	6	56	designed	design	VERB
eurjchem-1645	6	57	and	and	CCONJ
eurjchem-1645	6	58	synthesized	synthesize	VERB
eurjchem-1645	6	59	in	in	ADP
eurjchem-1645	6	60	large	large	ADJ
eurjchem-1645	6	61	scale	scale	NOUN
eurjchem-1645	6	62	(	(	PUNCT
eurjchem-1645	6	63	grams	gram	NOUN
eurjchem-1645	6	64	range	range	PROPN
eurjchem-1645	6	65	)	)	PUNCT
eurjchem-1645	6	66	.	.	PUNCT
eurjchem-1645	7	1	the	the	DET
eurjchem-1645	7	2	structures	structure	NOUN
eurjchem-1645	7	3	of	of	ADP
eurjchem-1645	7	4	the	the	DET
eurjchem-1645	7	5	synthesized	synthesize	VERB
eurjchem-1645	7	6	compounds	compound	NOUN
eurjchem-1645	7	7	were	be	AUX
eurjchem-1645	7	8	elucidated	elucidate	VERB
eurjchem-1645	7	9	and	and	CCONJ
eurjchem-1645	7	10	confirmed	confirm	VERB
eurjchem-1645	7	11	by	by	ADP
eurjchem-1645	7	12	1h	1h	NUM
eurjchem-1645	7	13	nmr	nmr	NOUN
eurjchem-1645	7	14	,	,	PUNCT
eurjchem-1645	7	15	13c	13c	NOUN
eurjchem-1645	7	16	nmr	nmr	NOUN
eurjchem-1645	7	17	,	,	PUNCT
eurjchem-1645	7	18	mass	mass	NOUN
eurjchem-1645	7	19	spectra	spectra	NOUN
eurjchem-1645	7	20	;	;	PUNCT
eurjchem-1645	7	21	and	and	CCONJ
eurjchem-1645	7	22	purity	purity	NOUN
eurjchem-1645	7	23	was	be	AUX
eurjchem-1645	7	24	also	also	ADV
eurjchem-1645	7	25	checked	check	VERB
eurjchem-1645	7	26	through	through	ADP
eurjchem-1645	7	27	lc	lc	PROPN
eurjchem-1645	7	28	/	/	SYM
eurjchem-1645	7	29	ms	ms	PROPN
eurjchem-1645	7	30	and	and	CCONJ
eurjchem-1645	7	31	hplc	hplc	PROPN
eurjchem-1645	7	32	analysis	analysis	NOUN
eurjchem-1645	7	33	.	.	PUNCT
eurjchem-1645	8	1	the	the	DET
eurjchem-1645	8	2	antiproliferative	antiproliferative	ADJ
eurjchem-1645	8	3	activity	activity	NOUN
eurjchem-1645	8	4	of	of	ADP
eurjchem-1645	8	5	the	the	DET
eurjchem-1645	8	6	compounds	compound	NOUN
eurjchem-1645	8	7	was	be	AUX
eurjchem-1645	8	8	checked	check	VERB
eurjchem-1645	8	9	for	for	ADP
eurjchem-1645	8	10	lung	lung	NOUN
eurjchem-1645	8	11	cancer	cancer	NOUN
eurjchem-1645	8	12	,	,	PUNCT
eurjchem-1645	8	13	cervical	cervical	ADJ
eurjchem-1645	8	14	cancer	cancer	NOUN
eurjchem-1645	8	15	,	,	PUNCT
eurjchem-1645	8	16	breast	breast	NOUN
eurjchem-1645	8	17	cancer	cancer	NOUN
eurjchem-1645	8	18	and	and	CCONJ
eurjchem-1645	8	19	prostate	prostate	NOUN
eurjchem-1645	8	20	cancer	cancer	NOUN
eurjchem-1645	8	21	on	on	ADP
eurjchem-1645	8	22	panel	panel	NOUN
eurjchem-1645	8	23	of	of	ADP
eurjchem-1645	8	24	four	four	NUM
eurjchem-1645	8	25	cell	cell	NOUN
eurjchem-1645	8	26	lines	line	NOUN
eurjchem-1645	8	27	.	.	PUNCT
eurjchem-1645	9	1	a	a	DET
eurjchem-1645	9	2	few	few	ADJ
eurjchem-1645	9	3	compounds	compound	NOUN
eurjchem-1645	9	4	(	(	PUNCT
eurjchem-1645	9	5	13c	13c	NOUN
eurjchem-1645	9	6	,	,	PUNCT
eurjchem-1645	9	7	13	13	NUM
eurjchem-1645	9	8	g	g	NOUN
eurjchem-1645	9	9	,	,	PUNCT
eurjchem-1645	9	10	15	15	NUM
eurjchem-1645	9	11	g	g	NOUN
eurjchem-1645	9	12	and	and	CCONJ
eurjchem-1645	9	13	15h	15h	NUM
eurjchem-1645	9	14	)	)	PUNCT
eurjchem-1645	9	15	showed	show	VERB
eurjchem-1645	9	16	promising	promising	ADJ
eurjchem-1645	9	17	antiproliferative	antiproliferative	ADJ
eurjchem-1645	9	18	activity	activity	NOUN
eurjchem-1645	9	19	in	in	ADP
eurjchem-1645	9	20	the	the	DET
eurjchem-1645	9	21	range	range	NOUN
eurjchem-1645	9	22	of	of	ADP
eurjchem-1645	9	23	5.12‐17.12	5.12‐17.12	NUM
eurjchem-1645	9	24	µm	µm	ADP
eurjchem-1645	9	25	which	which	PRON
eurjchem-1645	9	26	were	be	AUX
eurjchem-1645	9	27	further	far	ADV
eurjchem-1645	9	28	tested	test	VERB
eurjchem-1645	9	29	for	for	ADP
eurjchem-1645	9	30	their	their	PRON
eurjchem-1645	9	31	inhibitory	inhibitory	ADJ
eurjchem-1645	9	32	activity	activity	NOUN
eurjchem-1645	9	33	against	against	ADP
eurjchem-1645	9	34	panel	panel	NOUN
eurjchem-1645	9	35	of	of	ADP
eurjchem-1645	9	36	8	8	NUM
eurjchem-1645	9	37	human	human	ADJ
eurjchem-1645	9	38	kinases	kinase	NOUN
eurjchem-1645	9	39	at	at	ADP
eurjchem-1645	9	40	10	10	NUM
eurjchem-1645	9	41	µm	µm	ADP
eurjchem-1645	9	42	concentrations	concentration	NOUN
eurjchem-1645	9	43	.	.	PUNCT
eurjchem-1645	10	1	the	the	DET
eurjchem-1645	10	2	compounds	compound	NOUN
eurjchem-1645	10	3	13c	13c	NOUN
eurjchem-1645	10	4	,	,	PUNCT
eurjchem-1645	10	5	13	13	NUM
eurjchem-1645	10	6	g	g	NOUN
eurjchem-1645	10	7	,	,	PUNCT
eurjchem-1645	10	8	15	15	NUM
eurjchem-1645	10	9	g	g	NOUN
eurjchem-1645	10	10	and	and	CCONJ
eurjchem-1645	10	11	15h	15h	NUM
eurjchem-1645	10	12	shows	show	VERB
eurjchem-1645	10	13	prominent	prominent	ADJ
eurjchem-1645	10	14	inhibitory	inhibitory	ADJ
eurjchem-1645	10	15	activity	activity	NOUN
eurjchem-1645	10	16	against	against	ADP
eurjchem-1645	10	17	aurora‐a	aurora‐a	PROPN
eurjchem-1645	10	18	,	,	PUNCT
eurjchem-1645	10	19	aurora‐b	aurora‐b	NOUN
eurjchem-1645	10	20	,	,	PUNCT
eurjchem-1645	10	21	cdk5	cdk5	PROPN
eurjchem-1645	10	22	/	/	SYM
eurjchem-1645	10	23	p25	p25	PROPN
eurjchem-1645	10	24	and	and	CCONJ
eurjchem-1645	10	25	mtor	mtor	PROPN
eurjchem-1645	10	26	kinases	kinase	NOUN
eurjchem-1645	10	27	.	.	PUNCT
eurjchem-1645	11	1	keywords	keyword	VERB
eurjchem-1645	11	2	pd	pd	PROPN
eurjchem-1645	11	3	/	/	SYM
eurjchem-1645	11	4	c	c	PROPN
eurjchem-1645	11	5	antiproliferative	antiproliferative	NOUN
eurjchem-1645	11	6	aurora‐a	aurora‐a	PROPN
eurjchem-1645	11	7	kinases	kinases	PROPN
eurjchem-1645	11	8	5,6‐dihydropyrazole	5,6‐dihydropyrazole	PROPN
eurjchem-1645	11	9	tetrahydropyridine	tetrahydropyridine	PROPN
eurjchem-1645	11	10	4,5,6,7‐tetrahydropyrazole	4,5,6,7‐tetrahydropyrazole	PROPN
eurjchem-1645	11	11	cite	cite	VERB
eurjchem-1645	11	12	this	this	PRON
eurjchem-1645	11	13	:	:	PUNCT
eurjchem-1645	11	14	eur	eur	PROPN
eurjchem-1645	11	15	.	.	PUNCT
eurjchem-1645	12	1	j.	j.	PROPN
eurjchem-1645	12	2	chem	chem	PROPN
eurjchem-1645	12	3	.	.	PUNCT
eurjchem-1645	13	1	2017	2017	NUM
eurjchem-1645	13	2	,	,	PUNCT
eurjchem-1645	13	3	8(4	8(4	NUM
eurjchem-1645	13	4	)	)	PUNCT
eurjchem-1645	13	5	,	,	PUNCT
eurjchem-1645	13	6	400‐409	400‐409	NUM
eurjchem-1645	13	7	1	1	NUM
eurjchem-1645	13	8	.	.	PUNCT
eurjchem-1645	14	1	introduction	introduction	NOUN
eurjchem-1645	14	2	cancer	cancer	NOUN
eurjchem-1645	14	3	treatment	treatment	NOUN
eurjchem-1645	14	4	is	be	AUX
eurjchem-1645	14	5	difficult	difficult	ADJ
eurjchem-1645	14	6	due	due	ADJ
eurjchem-1645	14	7	to	to	ADP
eurjchem-1645	14	8	plethora	plethora	ADV
eurjchem-1645	14	9	of	of	ADP
eurjchem-1645	14	10	unwanted	unwanted	ADJ
eurjchem-1645	14	11	side	side	NOUN
eurjchem-1645	14	12	effects	effect	NOUN
eurjchem-1645	14	13	[	[	X
eurjchem-1645	14	14	1	1	NUM
eurjchem-1645	14	15	]	]	PUNCT
eurjchem-1645	14	16	.	.	PUNCT
eurjchem-1645	15	1	in	in	ADP
eurjchem-1645	15	2	present	present	ADJ
eurjchem-1645	15	3	study	study	NOUN
eurjchem-1645	15	4	,	,	PUNCT
eurjchem-1645	15	5	we	we	PRON
eurjchem-1645	15	6	have	have	AUX
eurjchem-1645	15	7	chosen	choose	VERB
eurjchem-1645	15	8	4,5,6,7‐	4,5,6,7‐	NUM
eurjchem-1645	15	9	tetrahydro‐1h‐pyrazolo[3,4‐c]pyridine	tetrahydro‐1h‐pyrazolo[3,4‐c]pyridine	NOUN
eurjchem-1645	15	10	and	and	CCONJ
eurjchem-1645	15	11	5,6‐dihydro‐1h‐	5,6‐dihydro‐1h‐	NUM
eurjchem-1645	15	12	pyrazolo[3,4‐c]pyridin‐7(4h)‐one	pyrazolo[3,4‐c]pyridin‐7(4h)‐one	NOUN
eurjchem-1645	15	13	as	as	ADP
eurjchem-1645	15	14	core	core	NOUN
eurjchem-1645	15	15	structure	structure	NOUN
eurjchem-1645	15	16	as	as	ADP
eurjchem-1645	15	17	4,5,6,7‐	4,5,6,7‐	NUM
eurjchem-1645	15	18	tetrahydro‐1h‐pyrazolo[3,4‐c]pyridine	tetrahydro‐1h‐pyrazolo[3,4‐c]pyridine	PRON
eurjchem-1645	15	19	is	be	AUX
eurjchem-1645	15	20	showing	show	VERB
eurjchem-1645	15	21	diversified	diversified	ADJ
eurjchem-1645	15	22	biological	biological	ADJ
eurjchem-1645	15	23	activities	activity	NOUN
eurjchem-1645	15	24	as	as	ADP
eurjchem-1645	15	25	anticancer	anticancer	NOUN
eurjchem-1645	15	26	activity	activity	NOUN
eurjchem-1645	16	1	[	[	X
eurjchem-1645	16	2	2	2	NUM
eurjchem-1645	16	3	]	]	PUNCT
eurjchem-1645	16	4	,	,	PUNCT
eurjchem-1645	16	5	5‐ht6	5‐ht6	NUM
eurjchem-1645	16	6	inhibitors	inhibitor	NOUN
eurjchem-1645	16	7	for	for	ADP
eurjchem-1645	16	8	pain	pain	NOUN
eurjchem-1645	16	9	treatment	treatment	NOUN
eurjchem-1645	16	10	[	[	X
eurjchem-1645	16	11	3	3	NUM
eurjchem-1645	16	12	]	]	PUNCT
eurjchem-1645	16	13	,	,	PUNCT
eurjchem-1645	16	14	inflammatory	inflammatory	ADJ
eurjchem-1645	16	15	disorders	disorder	NOUN
eurjchem-1645	16	16	[	[	X
eurjchem-1645	16	17	4	4	NUM
eurjchem-1645	16	18	]	]	PUNCT
eurjchem-1645	16	19	,	,	PUNCT
eurjchem-1645	16	20	gnrh	gnrh	NOUN
eurjchem-1645	16	21	receptor	receptor	NOUN
eurjchem-1645	16	22	antagonists	antagonist	NOUN
eurjchem-1645	16	23	[	[	X
eurjchem-1645	16	24	5	5	NUM
eurjchem-1645	16	25	]	]	PUNCT
eurjchem-1645	16	26	,	,	PUNCT
eurjchem-1645	16	27	kinase1	kinase1	NOUN
eurjchem-1645	16	28	inhibitors	inhibitor	NOUN
eurjchem-1645	17	1	[	[	X
eurjchem-1645	17	2	6	6	NUM
eurjchem-1645	17	3	]	]	PUNCT
eurjchem-1645	17	4	,	,	PUNCT
eurjchem-1645	17	5	cannabinoid	cannabinoid	X
eurjchem-1645	17	6	receptors	receptor	NOUN
eurjchem-1645	17	7	[	[	X
eurjchem-1645	17	8	7	7	NUM
eurjchem-1645	17	9	]	]	PUNCT
eurjchem-1645	17	10	,	,	PUNCT
eurjchem-1645	17	11	inhibitor	inhibitor	NOUN
eurjchem-1645	17	12	of	of	ADP
eurjchem-1645	17	13	blood	blood	NOUN
eurjchem-1645	17	14	coagulation	coagulation	NOUN
eurjchem-1645	17	15	factor	factor	NOUN
eurjchem-1645	17	16	xa	xa	PROPN
eurjchem-1645	18	1	[	[	X
eurjchem-1645	18	2	8	8	NUM
eurjchem-1645	18	3	]	]	PUNCT
eurjchem-1645	18	4	,	,	PUNCT
eurjchem-1645	18	5	pde4	pde4	NOUN
eurjchem-1645	18	6	inhibitor	inhibitor	NOUN
eurjchem-1645	19	1	[	[	X
eurjchem-1645	19	2	9	9	NUM
eurjchem-1645	19	3	]	]	PUNCT
eurjchem-1645	19	4	,	,	PUNCT
eurjchem-1645	19	5	cox‐2	cox‐2	X
eurjchem-1645	19	6	inhibitors	inhibitor	NOUN
eurjchem-1645	19	7	[	[	X
eurjchem-1645	19	8	10	10	NUM
eurjchem-1645	19	9	]	]	PUNCT
eurjchem-1645	19	10	,	,	PUNCT
eurjchem-1645	19	11	antimicrobial	antimicrobial	ADJ
eurjchem-1645	19	12	[	[	X
eurjchem-1645	19	13	11	11	NUM
eurjchem-1645	19	14	]	]	PUNCT
eurjchem-1645	19	15	and	and	CCONJ
eurjchem-1645	19	16	p13k	p13k	NOUN
eurjchem-1645	19	17	inhibitors	inhibitor	NOUN
eurjchem-1645	19	18	[	[	X
eurjchem-1645	19	19	12	12	NUM
eurjchem-1645	19	20	]	]	PUNCT
eurjchem-1645	19	21	.	.	PUNCT
eurjchem-1645	20	1	the	the	DET
eurjchem-1645	20	2	pyrazole	pyrazole	NOUN
eurjchem-1645	20	3	is	be	AUX
eurjchem-1645	20	4	known	know	VERB
eurjchem-1645	20	5	for	for	ADP
eurjchem-1645	20	6	adenine	adenine	ADJ
eurjchem-1645	20	7	mimetic	mimetic	ADJ
eurjchem-1645	20	8	pharmacophore	pharmacophore	NOUN
eurjchem-1645	20	9	and	and	CCONJ
eurjchem-1645	20	10	is	be	AUX
eurjchem-1645	20	11	useful	useful	ADJ
eurjchem-1645	20	12	in	in	ADP
eurjchem-1645	20	13	inhibitors	inhibitor	NOUN
eurjchem-1645	20	14	of	of	ADP
eurjchem-1645	20	15	several	several	ADJ
eurjchem-1645	20	16	classes	class	NOUN
eurjchem-1645	20	17	of	of	ADP
eurjchem-1645	20	18	kinases	kinase	NOUN
eurjchem-1645	20	19	like	like	ADP
eurjchem-1645	20	20	aurora	aurora	PROPN
eurjchem-1645	20	21	,	,	PUNCT
eurjchem-1645	20	22	cdk‐2	cdk‐2	PRON
eurjchem-1645	20	23	and	and	CCONJ
eurjchem-1645	20	24	map	map	VERB
eurjchem-1645	20	25	kinases	kinase	NOUN
eurjchem-1645	20	26	as	as	SCONJ
eurjchem-1645	20	27	these	these	PRON
eurjchem-1645	20	28	plays	play	VERB
eurjchem-1645	20	29	key	key	ADJ
eurjchem-1645	20	30	role	role	NOUN
eurjchem-1645	20	31	in	in	ADP
eurjchem-1645	20	32	drug	drug	NOUN
eurjchem-1645	20	33	discovery	discovery	NOUN
eurjchem-1645	21	1	[	[	X
eurjchem-1645	21	2	2	2	NUM
eurjchem-1645	21	3	]	]	PUNCT
eurjchem-1645	21	4	.	.	PUNCT
eurjchem-1645	22	1	the	the	DET
eurjchem-1645	22	2	tetrahydro‐1h‐	tetrahydro‐1h‐	PROPN
eurjchem-1645	22	3	pyrazole	pyrazole	PROPN
eurjchem-1645	22	4	and	and	CCONJ
eurjchem-1645	22	5	their	their	PRON
eurjchem-1645	22	6	derivatives	derivative	NOUN
eurjchem-1645	22	7	show	show	VERB
eurjchem-1645	22	8	diversifying	diversify	VERB
eurjchem-1645	22	9	activity	activity	NOUN
eurjchem-1645	22	10	.	.	PUNCT
eurjchem-1645	23	1	by	by	ADP
eurjchem-1645	23	2	considering	consider	VERB
eurjchem-1645	23	3	their	their	PRON
eurjchem-1645	23	4	biological	biological	ADJ
eurjchem-1645	23	5	importance	importance	NOUN
eurjchem-1645	23	6	herein	herein	NOUN
eurjchem-1645	23	7	we	we	PRON
eurjchem-1645	23	8	report	report	VERB
eurjchem-1645	23	9	the	the	DET
eurjchem-1645	23	10	synthesis	synthesis	NOUN
eurjchem-1645	23	11	of	of	ADP
eurjchem-1645	23	12	3‐(substituted)‐4,5,6,7‐tetrahydro‐6‐(substitu‐	3‐(substituted)‐4,5,6,7‐tetrahydro‐6‐(substitu‐	NUM
eurjchem-1645	23	13	ted)‐1h‐pyrazolo[3,4‐c]pyridine	ted)‐1h‐pyrazolo[3,4‐c]pyridine	NOUN
eurjchem-1645	23	14	and	and	CCONJ
eurjchem-1645	23	15	3‐(substituted)‐5,6‐di	3‐(substituted)‐5,6‐di	NUM
eurjchem-1645	23	16	hydro‐6‐(substituted)‐1h‐pyrazolo[3	hydro‐6‐(substituted)‐1h‐pyrazolo[3	PROPN
eurjchem-1645	23	17	,	,	PUNCT
eurjchem-1645	23	18	4‐c]pyridin‐7(4h)‐one	4‐c]pyridin‐7(4h)‐one	NUM
eurjchem-1645	23	19	and	and	CCONJ
eurjchem-1645	23	20	anticancer	anticancer	NOUN
eurjchem-1645	23	21	activity	activity	NOUN
eurjchem-1645	23	22	in	in	ADP
eurjchem-1645	23	23	cell	cell	NOUN
eurjchem-1645	23	24	line	line	NOUN
eurjchem-1645	23	25	along	along	ADP
eurjchem-1645	23	26	with	with	ADP
eurjchem-1645	23	27	kinase	kinase	PROPN
eurjchem-1645	23	28	inhibition	inhibition	NOUN
eurjchem-1645	23	29	study	study	NOUN
eurjchem-1645	23	30	.	.	PUNCT
eurjchem-1645	24	1	we	we	PRON
eurjchem-1645	24	2	have	have	VERB
eurjchem-1645	24	3	optimized	optimize	VERB
eurjchem-1645	24	4	routes	route	NOUN
eurjchem-1645	24	5	for	for	ADP
eurjchem-1645	24	6	their	their	PRON
eurjchem-1645	24	7	synthesis	synthesis	NOUN
eurjchem-1645	24	8	.	.	PUNCT
eurjchem-1645	25	1	the	the	DET
eurjchem-1645	25	2	synthetic	synthetic	ADJ
eurjchem-1645	25	3	methods	method	NOUN
eurjchem-1645	25	4	adopted	adopt	VERB
eurjchem-1645	25	5	for	for	ADP
eurjchem-1645	25	6	the	the	DET
eurjchem-1645	25	7	preparation	preparation	NOUN
eurjchem-1645	25	8	of	of	ADP
eurjchem-1645	25	9	the	the	DET
eurjchem-1645	25	10	title	title	NOUN
eurjchem-1645	25	11	compounds	compound	VERB
eurjchem-1645	25	12	13a‐h	13a‐h	NOUN
eurjchem-1645	25	13	and	and	CCONJ
eurjchem-1645	25	14	15a‐h	15a‐h	NOUN
eurjchem-1645	25	15	are	be	AUX
eurjchem-1645	25	16	depicted	depict	VERB
eurjchem-1645	25	17	in	in	ADP
eurjchem-1645	25	18	schemes	scheme	NOUN
eurjchem-1645	25	19	1	1	NUM
eurjchem-1645	25	20	and	and	CCONJ
eurjchem-1645	25	21	2	2	NUM
eurjchem-1645	25	22	presented	present	VERB
eurjchem-1645	25	23	below	below	ADV
eurjchem-1645	25	24	.	.	PUNCT
eurjchem-1645	26	1	2	2	X
eurjchem-1645	26	2	.	.	X
eurjchem-1645	27	1	experimental	experimental	ADJ
eurjchem-1645	27	2	2.1	2.1	NUM
eurjchem-1645	27	3	.	.	PUNCT
eurjchem-1645	28	1	reagent	reagent	NOUN
eurjchem-1645	28	2	and	and	CCONJ
eurjchem-1645	28	3	instrumentation	instrumentation	NOUN
eurjchem-1645	28	4	all	all	DET
eurjchem-1645	28	5	chemicals	chemical	NOUN
eurjchem-1645	28	6	,	,	PUNCT
eurjchem-1645	28	7	unless	unless	SCONJ
eurjchem-1645	28	8	otherwise	otherwise	ADV
eurjchem-1645	28	9	specified	specify	VERB
eurjchem-1645	28	10	,	,	PUNCT
eurjchem-1645	28	11	were	be	AUX
eurjchem-1645	28	12	purchased	purchase	VERB
eurjchem-1645	28	13	from	from	ADP
eurjchem-1645	28	14	commercial	commercial	ADJ
eurjchem-1645	28	15	sources	source	NOUN
eurjchem-1645	28	16	and	and	CCONJ
eurjchem-1645	28	17	were	be	AUX
eurjchem-1645	28	18	used	use	VERB
eurjchem-1645	28	19	without	without	ADP
eurjchem-1645	28	20	further	further	ADJ
eurjchem-1645	28	21	purification	purification	NOUN
eurjchem-1645	28	22	.	.	PUNCT
eurjchem-1645	29	1	the	the	DET
eurjchem-1645	29	2	major	major	ADJ
eurjchem-1645	29	3	chemicals	chemical	NOUN
eurjchem-1645	29	4	were	be	AUX
eurjchem-1645	29	5	purchased	purchase	VERB
eurjchem-1645	29	6	from	from	ADP
eurjchem-1645	29	7	sigma	sigma	PROPN
eurjchem-1645	29	8	aldrich	aldrich	PROPN
eurjchem-1645	29	9	and	and	CCONJ
eurjchem-1645	29	10	avra	avra	ADJ
eurjchem-1645	29	11	labs	lab	NOUN
eurjchem-1645	29	12	.	.	PUNCT
eurjchem-1645	30	1	the	the	DET
eurjchem-1645	30	2	development	development	NOUN
eurjchem-1645	30	3	of	of	ADP
eurjchem-1645	30	4	reactions	reaction	NOUN
eurjchem-1645	30	5	was	be	AUX
eurjchem-1645	30	6	monitored	monitor	VERB
eurjchem-1645	30	7	by	by	ADP
eurjchem-1645	30	8	thin	thin	ADJ
eurjchem-1645	30	9	layer	layer	NOUN
eurjchem-1645	30	10	chromatography	chromatography	NOUN
eurjchem-1645	30	11	(	(	PUNCT
eurjchem-1645	30	12	tlc	tlc	NOUN
eurjchem-1645	30	13	)	)	PUNCT
eurjchem-1645	30	14	analysis	analysis	NOUN
eurjchem-1645	30	15	on	on	ADP
eurjchem-1645	30	16	merck	merck	NOUN
eurjchem-1645	30	17	pre‐coated	pre‐coate	VERB
eurjchem-1645	30	18	silica	silica	NOUN
eurjchem-1645	30	19	gel	gel	NOUN
eurjchem-1645	30	20	60	60	NUM
eurjchem-1645	30	21	f254	f254	PROPN
eurjchem-1645	30	22	aluminum	aluminum	NOUN
eurjchem-1645	30	23	sheets	sheet	NOUN
eurjchem-1645	30	24	,	,	PUNCT
eurjchem-1645	30	25	visualized	visualize	VERB
eurjchem-1645	30	26	by	by	ADP
eurjchem-1645	30	27	uv	uv	NOUN
eurjchem-1645	30	28	light	light	NOUN
eurjchem-1645	30	29	.	.	PUNCT
eurjchem-1645	31	1	all	all	DET
eurjchem-1645	31	2	reactions	reaction	NOUN
eurjchem-1645	31	3	were	be	AUX
eurjchem-1645	31	4	carried	carry	VERB
eurjchem-1645	31	5	out	out	ADP
eurjchem-1645	31	6	under	under	ADP
eurjchem-1645	31	7	argon	argon	NOUN
eurjchem-1645	31	8	inert	inert	NOUN
eurjchem-1645	31	9	atmosphere	atmosphere	PROPN
eurjchem-1645	31	10	.	.	PUNCT
eurjchem-1645	32	1	melting	melt	VERB
eurjchem-1645	32	2	points	point	NOUN
eurjchem-1645	32	3	were	be	AUX
eurjchem-1645	32	4	recorded	record	VERB
eurjchem-1645	32	5	on	on	ADP
eurjchem-1645	32	6	srs	srs	PROPN
eurjchem-1645	32	7	optimelt	optimelt	PROPN
eurjchem-1645	32	8	.	.	PUNCT
eurjchem-1645	33	1	the	the	DET
eurjchem-1645	33	2	purity	purity	NOUN
eurjchem-1645	33	3	of	of	ADP
eurjchem-1645	33	4	intermediates	intermediate	NOUN
eurjchem-1645	33	5	was	be	AUX
eurjchem-1645	33	6	pursued	pursue	VERB
eurjchem-1645	33	7	by	by	ADP
eurjchem-1645	33	8	tlc	tlc	PROPN
eurjchem-1645	33	9	,	,	PUNCT
eurjchem-1645	33	10	nmr	nmr	NOUN
eurjchem-1645	33	11	,	,	PUNCT
eurjchem-1645	33	12	and	and	CCONJ
eurjchem-1645	33	13	lc‐	lc‐	ADJ
eurjchem-1645	33	14	ms	ms	PROPN
eurjchem-1645	33	15	.	.	PROPN
eurjchem-1645	33	16	all	all	DET
eurjchem-1645	33	17	final	final	ADJ
eurjchem-1645	33	18	compounds	compound	NOUN
eurjchem-1645	33	19	and	and	CCONJ
eurjchem-1645	33	20	intermediates	intermediate	NOUN
eurjchem-1645	33	21	are	be	AUX
eurjchem-1645	33	22	characterized	characterize	VERB
eurjchem-1645	33	23	by	by	ADP
eurjchem-1645	33	24	nmr	nmr	NOUN
eurjchem-1645	33	25	,	,	PUNCT
eurjchem-1645	33	26	lc‐ms	lc‐ms	NOUN
eurjchem-1645	33	27	and	and	CCONJ
eurjchem-1645	33	28	purity	purity	NOUN
eurjchem-1645	33	29	of	of	ADP
eurjchem-1645	33	30	final	final	ADJ
eurjchem-1645	33	31	compounds	compound	NOUN
eurjchem-1645	33	32	pursued	pursue	VERB
eurjchem-1645	33	33	by	by	ADP
eurjchem-1645	33	34	hplc	hplc	NOUN
eurjchem-1645	33	35	and	and	CCONJ
eurjchem-1645	33	36	all	all	DET
eurjchem-1645	33	37	structures	structure	NOUN
eurjchem-1645	33	38	are	be	AUX
eurjchem-1645	33	39	consistent	consistent	ADJ
eurjchem-1645	33	40	with	with	ADP
eurjchem-1645	33	41	proposed	propose	VERB
eurjchem-1645	33	42	struc‐	struc‐	PROPN
eurjchem-1645	33	43	tures	ture	NOUN
eurjchem-1645	33	44	characterization	characterization	NOUN
eurjchem-1645	33	45	.	.	PUNCT
eurjchem-1645	34	1	the	the	DET
eurjchem-1645	34	2	1h	1h	NUM
eurjchem-1645	34	3	nmr	nmr	NOUN
eurjchem-1645	34	4	spectra	spectra	NOUN
eurjchem-1645	34	5	were	be	AUX
eurjchem-1645	34	6	recorded	record	VERB
eurjchem-1645	34	7	on	on	ADP
eurjchem-1645	34	8	varian	varian	PROPN
eurjchem-1645	34	9	nmr	nmr	NOUN
eurjchem-1645	34	10	(	(	PUNCT
eurjchem-1645	34	11	400	400	NUM
eurjchem-1645	34	12	mhz	mhz	NOUN
eurjchem-1645	34	13	)	)	PUNCT
eurjchem-1645	34	14	spectrometer	spectrometer	NOUN
eurjchem-1645	34	15	.	.	PUNCT
eurjchem-1645	35	1	the	the	DET
eurjchem-1645	35	2	13c	13c	NUM
eurjchem-1645	35	3	nmr	nmr	NOUN
eurjchem-1645	35	4	spectra	spectra	NOUN
eurjchem-1645	35	5	were	be	AUX
eurjchem-1645	35	6	recorded	record	VERB
eurjchem-1645	35	7	on	on	ADP
eurjchem-1645	35	8	varian	varian	PROPN
eurjchem-1645	35	9	nmr	nmr	NOUN
eurjchem-1645	35	10	(	(	PUNCT
eurjchem-1645	35	11	100	100	NUM
eurjchem-1645	35	12	mhz	mhz	NOUN
eurjchem-1645	35	13	)	)	PUNCT
eurjchem-1645	35	14	spectrometer	spectrometer	NOUN
eurjchem-1645	35	15	.	.	PUNCT
eurjchem-1645	36	1	pawar	pawar	PROPN
eurjchem-1645	36	2	et	et	PROPN
eurjchem-1645	36	3	al	al	PROPN
eurjchem-1645	36	4	.	.	PUNCT
eurjchem-1645	36	5	/	/	SYM
eurjchem-1645	36	6	european	european	PROPN
eurjchem-1645	36	7	journal	journal	PROPN
eurjchem-1645	36	8	of	of	ADP
eurjchem-1645	36	9	chemistry	chemistry	NOUN
eurjchem-1645	36	10	8	8	NUM
eurjchem-1645	36	11	(	(	PUNCT
eurjchem-1645	36	12	4	4	NUM
eurjchem-1645	36	13	)	)	PUNCT
eurjchem-1645	36	14	(	(	PUNCT
eurjchem-1645	36	15	2017	2017	NUM
eurjchem-1645	36	16	)	)	PUNCT
eurjchem-1645	36	17	400‐409	400‐409	NUM
eurjchem-1645	36	18	401	401	NUM
eurjchem-1645	36	19	n	n	NOUN
eurjchem-1645	36	20	boc	boc	VERB
eurjchem-1645	36	21	o	o	NOUN
eurjchem-1645	36	22	n	n	CCONJ
eurjchem-1645	36	23	boc	boc	VERB
eurjchem-1645	36	24	o	o	PROPN
eurjchem-1645	36	25	n	n	CCONJ
eurjchem-1645	36	26	n	n	ADV
eurjchem-1645	36	27	boc	boc	VERB
eurjchem-1645	36	28	n	n	CCONJ
eurjchem-1645	36	29	n	n	NOUN
eurjchem-1645	36	30	h	h	NOUN
eurjchem-1645	36	31	n	n	ADV
eurjchem-1645	36	32	boc	boc	VERB
eurjchem-1645	36	33	n	n	CCONJ
eurjchem-1645	36	34	n	n	NOUN
eurjchem-1645	36	35	boc	boc	VERB
eurjchem-1645	36	36	hn	hn	PROPN
eurjchem-1645	36	37	n	n	NOUN
eurjchem-1645	36	38	n	n	ADV
eurjchem-1645	36	39	boc	boc	VERB
eurjchem-1645	36	40	hn	hn	PROPN
eurjchem-1645	36	41	n	n	CCONJ
eurjchem-1645	36	42	n	n	ADV
eurjchem-1645	36	43	boc	boc	VERB
eurjchem-1645	36	44	br	br	ADP
eurjchem-1645	36	45	hn	hn	PROPN
eurjchem-1645	36	46	n	n	CCONJ
eurjchem-1645	36	47	n	n	PRON
eurjchem-1645	36	48	boc	boc	VERB
eurjchem-1645	37	1	oh	oh	INTJ
eurjchem-1645	37	2	n	n	CCONJ
eurjchem-1645	37	3	n	n	CCONJ
eurjchem-1645	37	4	n	n	ADV
eurjchem-1645	37	5	boc	boc	VERB
eurjchem-1645	37	6	oh	oh	INTJ
eurjchem-1645	37	7	n	n	CCONJ
eurjchem-1645	37	8	n	n	CCONJ
eurjchem-1645	37	9	n	n	ADV
eurjchem-1645	37	10	boc	boc	NOUN
eurjchem-1645	37	11	o	o	NOUN
eurjchem-1645	37	12	o	o	X
eurjchem-1645	38	1	ff	ff	INTJ
eurjchem-1645	38	2	f	f	PROPN
eurjchem-1645	38	3	n	n	CCONJ
eurjchem-1645	38	4	n	n	CCONJ
eurjchem-1645	38	5	n	n	ADV
eurjchem-1645	38	6	boc	boc	NOUN
eurjchem-1645	38	7	r1	r1	NOUN
eurjchem-1645	38	8	hn	hn	PROPN
eurjchem-1645	38	9	n	n	CCONJ
eurjchem-1645	38	10	n	n	ADV
eurjchem-1645	38	11	boc	boc	VERB
eurjchem-1645	38	12	r1	r1	PROPN
eurjchem-1645	38	13	n	n	CCONJ
eurjchem-1645	38	14	n	n	CCONJ
eurjchem-1645	38	15	n	n	ADV
eurjchem-1645	38	16	boc	boc	NOUN
eurjchem-1645	38	17	r1	r1	NOUN
eurjchem-1645	38	18	r2	r2	PROPN
eurjchem-1645	38	19	n	n	CCONJ
eurjchem-1645	38	20	n	n	CCONJ
eurjchem-1645	38	21	n	n	NOUN
eurjchem-1645	38	22	h	h	NOUN
eurjchem-1645	38	23	r1	r1	NOUN
eurjchem-1645	38	24	r2	r2	PROPN
eurjchem-1645	38	25	1	1	NUM
eurjchem-1645	38	26	2	2	NUM
eurjchem-1645	38	27	67	67	NUM
eurjchem-1645	38	28	3	3	NUM
eurjchem-1645	38	29	4	4	NUM
eurjchem-1645	38	30	5	5	NUM
eurjchem-1645	38	31	8	8	NUM
eurjchem-1645	38	32	9	9	NUM
eurjchem-1645	38	33	10a	10a	NOUN
eurjchem-1645	38	34	-	-	PUNCT
eurjchem-1645	38	35	d	d	NOUN
eurjchem-1645	38	36	11a	11a	NOUN
eurjchem-1645	38	37	-	-	SYM
eurjchem-1645	38	38	d	d	NOUN
eurjchem-1645	38	39	13a	13a	PROPN
eurjchem-1645	38	40	-	-	PUNCT
eurjchem-1645	38	41	h	h	NOUN
eurjchem-1645	38	42	12a	12a	NOUN
eurjchem-1645	38	43	-	-	PUNCT
eurjchem-1645	38	44	h	h	NOUN
eurjchem-1645	38	45	g	g	PROPN
eurjchem-1645	38	46	b	b	PROPN
eurjchem-1645	38	47	c	c	PROPN
eurjchem-1645	38	48	d	d	PROPN
eurjchem-1645	38	49	a	a	DET
eurjchem-1645	38	50	ef	ef	X
eurjchem-1645	38	51	h	h	NOUN
eurjchem-1645	39	1	i	i	INTJ
eurjchem-1645	39	2	j	j	PROPN
eurjchem-1645	39	3	k	k	PROPN
eurjchem-1645	39	4	l	l	NOUN
eurjchem-1645	39	5	reagents	reagent	NOUN
eurjchem-1645	39	6	and	and	CCONJ
eurjchem-1645	39	7	conditions	condition	NOUN
eurjchem-1645	39	8	:	:	PUNCT
eurjchem-1645	39	9	(	(	PUNCT
eurjchem-1645	39	10	a	a	X
eurjchem-1645	39	11	)	)	PUNCT
eurjchem-1645	39	12	dmf‐dma	dmf‐dma	NOUN
eurjchem-1645	39	13	at	at	ADP
eurjchem-1645	39	14	100	100	NUM
eurjchem-1645	39	15	°	°	NOUN
eurjchem-1645	39	16	c	c	NOUN
eurjchem-1645	39	17	,	,	PUNCT
eurjchem-1645	39	18	1	1	NUM
eurjchem-1645	39	19	h	h	NOUN
eurjchem-1645	39	20	;	;	PUNCT
eurjchem-1645	39	21	(	(	PUNCT
eurjchem-1645	39	22	b	b	X
eurjchem-1645	39	23	)	)	PUNCT
eurjchem-1645	39	24	n2h4.h2o	n2h4.h2o	NOUN
eurjchem-1645	39	25	,	,	PUNCT
eurjchem-1645	39	26	etoh	etoh	NOUN
eurjchem-1645	39	27	,	,	PUNCT
eurjchem-1645	39	28	80	80	NUM
eurjchem-1645	39	29	°	°	NOUN
eurjchem-1645	39	30	c	c	NOUN
eurjchem-1645	39	31	,	,	PUNCT
eurjchem-1645	39	32	8	8	NUM
eurjchem-1645	39	33	h	h	NOUN
eurjchem-1645	39	34	;	;	PUNCT
eurjchem-1645	39	35	(	(	PUNCT
eurjchem-1645	39	36	c	c	X
eurjchem-1645	39	37	)	)	PUNCT
eurjchem-1645	39	38	(	(	PUNCT
eurjchem-1645	39	39	boc)2o	boc)2o	PROPN
eurjchem-1645	39	40	,	,	PUNCT
eurjchem-1645	39	41	tea	tea	NOUN
eurjchem-1645	39	42	,	,	PUNCT
eurjchem-1645	39	43	dcm	dcm	PROPN
eurjchem-1645	39	44	,	,	PUNCT
eurjchem-1645	39	45	room	room	NOUN
eurjchem-1645	39	46	temperature	temperature	NOUN
eurjchem-1645	39	47	,	,	PUNCT
eurjchem-1645	39	48	3	3	NUM
eurjchem-1645	39	49	h	h	NOUN
eurjchem-1645	39	50	;	;	PUNCT
eurjchem-1645	39	51	(	(	PUNCT
eurjchem-1645	39	52	d	d	X
eurjchem-1645	39	53	)	)	PUNCT
eurjchem-1645	39	54	2	2	NUM
eurjchem-1645	39	55	n	n	NOUN
eurjchem-1645	39	56	aq	aq	NOUN
eurjchem-1645	39	57	.	.	PUNCT
eurjchem-1645	39	58	hcl	hcl	PROPN
eurjchem-1645	39	59	,	,	PUNCT
eurjchem-1645	39	60	room	room	NOUN
eurjchem-1645	39	61	temperature	temperature	NOUN
eurjchem-1645	39	62	,	,	PUNCT
eurjchem-1645	39	63	2	2	NUM
eurjchem-1645	39	64	h	h	NOUN
eurjchem-1645	39	65	;	;	PUNCT
eurjchem-1645	39	66	(	(	PUNCT
eurjchem-1645	39	67	e	e	NOUN
eurjchem-1645	39	68	)	)	PUNCT
eurjchem-1645	39	69	pyridine	pyridine	ADJ
eurjchem-1645	39	70	br2	br2	PROPN
eurjchem-1645	39	71	,	,	PUNCT
eurjchem-1645	39	72	thf	thf	NOUN
eurjchem-1645	39	73	,	,	PUNCT
eurjchem-1645	39	74	room	room	NOUN
eurjchem-1645	39	75	temperature	temperature	NOUN
eurjchem-1645	39	76	,	,	PUNCT
eurjchem-1645	39	77	3	3	NUM
eurjchem-1645	39	78	h	h	NOUN
eurjchem-1645	39	79	;	;	PUNCT
eurjchem-1645	39	80	(	(	PUNCT
eurjchem-1645	39	81	f	f	X
eurjchem-1645	39	82	)	)	PUNCT
eurjchem-1645	39	83	2	2	NUM
eurjchem-1645	39	84	n	n	DET
eurjchem-1645	39	85	naoh	naoh	NOUN
eurjchem-1645	39	86	,	,	PUNCT
eurjchem-1645	39	87	100	100	NUM
eurjchem-1645	39	88	°	°	NOUN
eurjchem-1645	39	89	c	c	NOUN
eurjchem-1645	39	90	,	,	PUNCT
eurjchem-1645	39	91	3	3	NUM
eurjchem-1645	39	92	h	h	NOUN
eurjchem-1645	39	93	(	(	PUNCT
eurjchem-1645	39	94	g	g	NOUN
eurjchem-1645	39	95	)	)	PUNCT
eurjchem-1645	39	96	benzyl	benzyl	NOUN
eurjchem-1645	39	97	bromide	bromide	NOUN
eurjchem-1645	39	98	,	,	PUNCT
eurjchem-1645	39	99	2,6‐lutidine	2,6‐lutidine	NUM
eurjchem-1645	39	100	,	,	PUNCT
eurjchem-1645	39	101	dmap	dmap	NOUN
eurjchem-1645	39	102	,	,	PUNCT
eurjchem-1645	39	103	thf	thf	NOUN
eurjchem-1645	39	104	,	,	PUNCT
eurjchem-1645	39	105	room	room	NOUN
eurjchem-1645	39	106	temperature	temperature	NOUN
eurjchem-1645	39	107	,	,	PUNCT
eurjchem-1645	39	108	8	8	NUM
eurjchem-1645	39	109	h	h	NOUN
eurjchem-1645	39	110	;	;	PUNCT
eurjchem-1645	39	111	(	(	PUNCT
eurjchem-1645	39	112	h	h	NOUN
eurjchem-1645	39	113	)	)	PUNCT
eurjchem-1645	39	114	triflic	triflic	ADJ
eurjchem-1645	39	115	anhydride	anhydride	NOUN
eurjchem-1645	39	116	,	,	PUNCT
eurjchem-1645	39	117	tea	tea	NOUN
eurjchem-1645	39	118	,	,	PUNCT
eurjchem-1645	39	119	dcm	dcm	PROPN
eurjchem-1645	39	120	,	,	PUNCT
eurjchem-1645	39	121	room	room	NOUN
eurjchem-1645	39	122	temperature	temperature	NOUN
eurjchem-1645	39	123	,	,	PUNCT
eurjchem-1645	39	124	6	6	NUM
eurjchem-1645	39	125	h	h	NOUN
eurjchem-1645	39	126	;	;	PUNCT
eurjchem-1645	39	127	(	(	PUNCT
eurjchem-1645	39	128	i	i	NOUN
eurjchem-1645	39	129	)	)	PUNCT
eurjchem-1645	39	130	aromatic	aromatic	ADJ
eurjchem-1645	39	131	boronic	boronic	ADJ
eurjchem-1645	39	132	acid	acid	NOUN
eurjchem-1645	39	133	,	,	PUNCT
eurjchem-1645	39	134	pd2(dba)3	pd2(dba)3	ADJ
eurjchem-1645	39	135	,	,	PUNCT
eurjchem-1645	39	136	ruphos	ruphos	NOUN
eurjchem-1645	39	137	,	,	PUNCT
eurjchem-1645	39	138	cs2co3	cs2co3	ADJ
eurjchem-1645	39	139	,	,	PUNCT
eurjchem-1645	39	140	toluene	toluene	NOUN
eurjchem-1645	39	141	,	,	PUNCT
eurjchem-1645	39	142	100	100	NUM
eurjchem-1645	39	143	°	°	NOUN
eurjchem-1645	39	144	c	c	NOUN
eurjchem-1645	39	145	,	,	PUNCT
eurjchem-1645	39	146	6	6	NUM
eurjchem-1645	39	147	h	h	NOUN
eurjchem-1645	39	148	,	,	PUNCT
eurjchem-1645	39	149	(	(	PUNCT
eurjchem-1645	39	150	general	general	ADJ
eurjchem-1645	39	151	procedure	procedure	NOUN
eurjchem-1645	39	152	)	)	PUNCT
eurjchem-1645	39	153	;	;	PUNCT
eurjchem-1645	39	154	(	(	PUNCT
eurjchem-1645	39	155	j	j	NOUN
eurjchem-1645	39	156	)	)	PUNCT
eurjchem-1645	39	157	pd	pd	PROPN
eurjchem-1645	39	158	/	/	SYM
eurjchem-1645	39	159	c	c	PROPN
eurjchem-1645	39	160	,	,	PUNCT
eurjchem-1645	39	161	h2	h2	PROPN
eurjchem-1645	39	162	,	,	PUNCT
eurjchem-1645	39	163	meoh	meoh	NOUN
eurjchem-1645	39	164	,	,	PUNCT
eurjchem-1645	39	165	50	50	NUM
eurjchem-1645	39	166	psi	psi	NOUN
eurjchem-1645	39	167	,	,	PUNCT
eurjchem-1645	39	168	room	room	NOUN
eurjchem-1645	39	169	temperature	temperature	NOUN
eurjchem-1645	39	170	,	,	PUNCT
eurjchem-1645	39	171	3	3	NUM
eurjchem-1645	39	172	h	h	NOUN
eurjchem-1645	39	173	(	(	PUNCT
eurjchem-1645	39	174	general	general	ADJ
eurjchem-1645	39	175	procedure	procedure	NOUN
eurjchem-1645	39	176	)	)	PUNCT
eurjchem-1645	39	177	;	;	PUNCT
eurjchem-1645	39	178	(	(	PUNCT
eurjchem-1645	39	179	k	k	NOUN
eurjchem-1645	39	180	)	)	PUNCT
eurjchem-1645	39	181	alkyl	alkyl	ADJ
eurjchem-1645	39	182	bromide	bromide	NOUN
eurjchem-1645	39	183	,	,	PUNCT
eurjchem-1645	39	184	2,6‐lutidine	2,6‐lutidine	NUM
eurjchem-1645	39	185	,	,	PUNCT
eurjchem-1645	39	186	dmap	dmap	NOUN
eurjchem-1645	39	187	,	,	PUNCT
eurjchem-1645	39	188	thf	thf	NOUN
eurjchem-1645	39	189	,	,	PUNCT
eurjchem-1645	39	190	room	room	NOUN
eurjchem-1645	39	191	temperature	temperature	NOUN
eurjchem-1645	39	192	,	,	PUNCT
eurjchem-1645	39	193	8	8	NUM
eurjchem-1645	39	194	h	h	NOUN
eurjchem-1645	39	195	(	(	PUNCT
eurjchem-1645	39	196	general	general	ADJ
eurjchem-1645	39	197	procedure	procedure	NOUN
eurjchem-1645	39	198	)	)	PUNCT
eurjchem-1645	39	199	;	;	PUNCT
eurjchem-1645	39	200	(	(	PUNCT
eurjchem-1645	39	201	l	l	NOUN
eurjchem-1645	39	202	)	)	PUNCT
eurjchem-1645	39	203	6	6	NUM
eurjchem-1645	39	204	n	n	NUM
eurjchem-1645	39	205	aq	aq	NOUN
eurjchem-1645	39	206	.	.	PUNCT
eurjchem-1645	39	207	hcl	hcl	PROPN
eurjchem-1645	39	208	,	,	PUNCT
eurjchem-1645	39	209	room	room	NOUN
eurjchem-1645	39	210	temperature	temperature	NOUN
eurjchem-1645	39	211	,	,	PUNCT
eurjchem-1645	39	212	6	6	NUM
eurjchem-1645	39	213	h	h	NOUN
eurjchem-1645	39	214	(	(	PUNCT
eurjchem-1645	39	215	general	general	ADJ
eurjchem-1645	39	216	procedure	procedure	NOUN
eurjchem-1645	39	217	)	)	PUNCT
eurjchem-1645	39	218	.	.	PUNCT
eurjchem-1645	40	1	scheme	scheme	NOUN
eurjchem-1645	40	2	1	1	NUM
eurjchem-1645	40	3	the	the	DET
eurjchem-1645	40	4	chemical	chemical	ADJ
eurjchem-1645	40	5	shifts	shift	NOUN
eurjchem-1645	40	6	are	be	AUX
eurjchem-1645	40	7	reported	report	VERB
eurjchem-1645	40	8	as	as	ADP
eurjchem-1645	40	9	nmr	nmr	NOUN
eurjchem-1645	40	10	spectra	spectra	ADJ
eurjchem-1645	40	11	δppm	δppm	ADJ
eurjchem-1645	40	12	units	unit	NOUN
eurjchem-1645	40	13	.	.	PUNCT
eurjchem-1645	41	1	the	the	DET
eurjchem-1645	41	2	following	follow	VERB
eurjchem-1645	41	3	abbreviations	abbreviation	NOUN
eurjchem-1645	41	4	are	be	AUX
eurjchem-1645	41	5	used	use	VERB
eurjchem-1645	41	6	;	;	PUNCT
eurjchem-1645	41	7	singlet	singlet	NOUN
eurjchem-1645	41	8	(	(	PUNCT
eurjchem-1645	41	9	s	s	NOUN
eurjchem-1645	41	10	)	)	PUNCT
eurjchem-1645	41	11	,	,	PUNCT
eurjchem-1645	41	12	doublet	doublet	NOUN
eurjchem-1645	41	13	(	(	PUNCT
eurjchem-1645	41	14	d	d	NOUN
eurjchem-1645	41	15	)	)	PUNCT
eurjchem-1645	41	16	,	,	PUNCT
eurjchem-1645	41	17	triplet	triplet	NOUN
eurjchem-1645	41	18	(	(	PUNCT
eurjchem-1645	41	19	t	t	NOUN
eurjchem-1645	41	20	)	)	PUNCT
eurjchem-1645	41	21	,	,	PUNCT
eurjchem-1645	41	22	quartet	quartet	NOUN
eurjchem-1645	41	23	(	(	PUNCT
eurjchem-1645	41	24	q	q	NOUN
eurjchem-1645	41	25	)	)	PUNCT
eurjchem-1645	41	26	,	,	PUNCT
eurjchem-1645	41	27	multiplet	multiplet	NOUN
eurjchem-1645	41	28	(	(	PUNCT
eurjchem-1645	41	29	m	m	NOUN
eurjchem-1645	41	30	)	)	PUNCT
eurjchem-1645	41	31	and	and	CCONJ
eurjchem-1645	41	32	broad	broad	ADJ
eurjchem-1645	41	33	(	(	PUNCT
eurjchem-1645	41	34	br	br	NOUN
eurjchem-1645	41	35	)	)	PUNCT
eurjchem-1645	41	36	.	.	PUNCT
eurjchem-1645	42	1	mass	mass	PROPN
eurjchem-1645	42	2	spectra	spectra	PROPN
eurjchem-1645	42	3	were	be	AUX
eurjchem-1645	42	4	taken	take	VERB
eurjchem-1645	42	5	using	use	VERB
eurjchem-1645	42	6	varian	varian	NOUN
eurjchem-1645	42	7	vg	vg	ADP
eurjchem-1645	42	8	7070	7070	NUM
eurjchem-1645	42	9	spectrometer	spectrometer	NOUN
eurjchem-1645	42	10	at	at	ADP
eurjchem-1645	42	11	nominal	nominal	ADJ
eurjchem-1645	42	12	5000	5000	NUM
eurjchem-1645	42	13	resolution	resolution	NOUN
eurjchem-1645	42	14	.	.	PUNCT
eurjchem-1645	43	1	the	the	DET
eurjchem-1645	43	2	purity	purity	NOUN
eurjchem-1645	43	3	of	of	ADP
eurjchem-1645	43	4	final	final	ADJ
eurjchem-1645	43	5	compounds	compound	NOUN
eurjchem-1645	43	6	was	be	AUX
eurjchem-1645	43	7	determined	determine	VERB
eurjchem-1645	43	8	by	by	ADP
eurjchem-1645	43	9	hplc	hplc	NOUN
eurjchem-1645	43	10	on	on	ADP
eurjchem-1645	43	11	an	an	DET
eurjchem-1645	43	12	alltech	alltech	ADJ
eurjchem-1645	43	13	alltima	alltima	NOUN
eurjchem-1645	43	14	c18	c18	NOUN
eurjchem-1645	43	15	column	column	NOUN
eurjchem-1645	43	16	(	(	PUNCT
eurjchem-1645	43	17	3.2	3.2	NUM
eurjchem-1645	43	18	×	×	NOUN
eurjchem-1645	43	19	150	150	NUM
eurjchem-1645	43	20	mm	mm	NOUN
eurjchem-1645	43	21	,	,	PUNCT
eurjchem-1645	43	22	5	5	NUM
eurjchem-1645	43	23	µm	µm	NOUN
eurjchem-1645	43	24	)	)	PUNCT
eurjchem-1645	43	25	eluting	eluting	NOUN
eurjchem-1645	43	26	with	with	ADP
eurjchem-1645	43	27	5‐80	5‐80	NUM
eurjchem-1645	43	28	%	%	NOUN
eurjchem-1645	43	29	acetonitrile	acetonitrile	NOUN
eurjchem-1645	43	30	/	/	PUNCT
eurjchem-1645	43	31	45	45	NUM
eurjchem-1645	43	32	nm	nm	ADJ
eurjchem-1645	43	33	sodium	sodium	NOUN
eurjchem-1645	43	34	bicarbonate	bicarbonate	NOUN
eurjchem-1645	43	35	.	.	PUNCT
eurjchem-1645	44	1	2.2	2.2	NUM
eurjchem-1645	44	2	.	.	PUNCT
eurjchem-1645	44	3	synthesis	synthesis	NOUN
eurjchem-1645	44	4	2.2.1	2.2.1	NUM
eurjchem-1645	44	5	.	.	PUNCT
eurjchem-1645	44	6	synthesis	synthesis	NOUN
eurjchem-1645	44	7	of	of	ADP
eurjchem-1645	44	8	tert‐butyl‐4‐((dimethylamino)methyl	tert‐butyl‐4‐((dimethylamino)methyl	NOUN
eurjchem-1645	44	9	ene)‐3‐oxopiperidine‐1‐carboxylate	ene)‐3‐oxopiperidine‐1‐carboxylate	PROPN
eurjchem-1645	44	10	(	(	PUNCT
eurjchem-1645	44	11	2	2	NUM
eurjchem-1645	44	12	)	)	PUNCT
eurjchem-1645	44	13	,	,	PUNCT
eurjchem-1645	44	14	step	step	NOUN
eurjchem-1645	44	15	(	(	PUNCT
eurjchem-1645	44	16	a	a	NOUN
eurjchem-1645	44	17	)	)	PUNCT
eurjchem-1645	44	18	to	to	ADP
eurjchem-1645	44	19	a	a	DET
eurjchem-1645	44	20	stirred	stir	VERB
eurjchem-1645	44	21	solution	solution	NOUN
eurjchem-1645	44	22	of	of	ADP
eurjchem-1645	44	23	n‐tert‐butoxycarbonyl‐3‐piperi‐	n‐tert‐butoxycarbonyl‐3‐piperi‐	PROPN
eurjchem-1645	44	24	done	do	VERB
eurjchem-1645	44	25	(	(	PUNCT
eurjchem-1645	44	26	1	1	NUM
eurjchem-1645	44	27	)	)	PUNCT
eurjchem-1645	44	28	(	(	PUNCT
eurjchem-1645	44	29	10.0	10.0	NUM
eurjchem-1645	44	30	g	g	NOUN
eurjchem-1645	44	31	,	,	PUNCT
eurjchem-1645	44	32	50.2	50.2	NUM
eurjchem-1645	44	33	mmol	mmol	NOUN
eurjchem-1645	44	34	)	)	PUNCT
eurjchem-1645	44	35	in	in	ADP
eurjchem-1645	44	36	n	n	CCONJ
eurjchem-1645	44	37	,	,	PUNCT
eurjchem-1645	44	38	n‐dimethylformamide	n‐dimethylformamide	X
eurjchem-1645	44	39	dimethylacetal	dimethylacetal	ADJ
eurjchem-1645	44	40	(	(	PUNCT
eurjchem-1645	44	41	50	50	NUM
eurjchem-1645	44	42	ml	ml	NOUN
eurjchem-1645	44	43	)	)	PUNCT
eurjchem-1645	44	44	.	.	PUNCT
eurjchem-1645	45	1	the	the	DET
eurjchem-1645	45	2	reaction	reaction	NOUN
eurjchem-1645	45	3	mixture	mixture	NOUN
eurjchem-1645	45	4	was	be	AUX
eurjchem-1645	45	5	heated	heat	VERB
eurjchem-1645	45	6	at	at	ADP
eurjchem-1645	45	7	100	100	NUM
eurjchem-1645	45	8	°	°	ADP
eurjchem-1645	45	9	c	c	NOUN
eurjchem-1645	45	10	for	for	ADP
eurjchem-1645	45	11	1	1	NUM
eurjchem-1645	45	12	h.	h.	NOUN
eurjchem-1645	45	13	progress	progress	NOUN
eurjchem-1645	45	14	of	of	ADP
eurjchem-1645	45	15	reaction	reaction	NOUN
eurjchem-1645	45	16	was	be	AUX
eurjchem-1645	45	17	monitored	monitor	VERB
eurjchem-1645	45	18	by	by	ADP
eurjchem-1645	45	19	lc	lc	PROPN
eurjchem-1645	45	20	/	/	SYM
eurjchem-1645	45	21	ms	ms	NOUN
eurjchem-1645	45	22	for	for	ADP
eurjchem-1645	45	23	the	the	DET
eurjchem-1645	45	24	consumption	consumption	NOUN
eurjchem-1645	45	25	of	of	ADP
eurjchem-1645	45	26	starting	start	VERB
eurjchem-1645	45	27	material	material	NOUN
eurjchem-1645	45	28	.	.	PUNCT
eurjchem-1645	46	1	after	after	ADP
eurjchem-1645	46	2	completion	completion	NOUN
eurjchem-1645	46	3	the	the	DET
eurjchem-1645	46	4	reaction	reaction	NOUN
eurjchem-1645	46	5	,	,	PUNCT
eurjchem-1645	46	6	the	the	DET
eurjchem-1645	46	7	reaction	reaction	NOUN
eurjchem-1645	46	8	mixture	mixture	NOUN
eurjchem-1645	46	9	cooled	cool	VERB
eurjchem-1645	46	10	to	to	ADP
eurjchem-1645	46	11	room	room	NOUN
eurjchem-1645	46	12	temperature	temperature	NOUN
eurjchem-1645	46	13	and	and	CCONJ
eurjchem-1645	46	14	evaporated	evaporate	VERB
eurjchem-1645	46	15	under	under	ADP
eurjchem-1645	46	16	reduced	reduce	VERB
eurjchem-1645	46	17	pressure	pressure	NOUN
eurjchem-1645	46	18	to	to	PART
eurjchem-1645	46	19	obtain	obtain	VERB
eurjchem-1645	46	20	yellow	yellow	ADJ
eurjchem-1645	46	21	gummy	gummy	ADJ
eurjchem-1645	46	22	material	material	NOUN
eurjchem-1645	46	23	.	.	PUNCT
eurjchem-1645	47	1	the	the	DET
eurjchem-1645	47	2	obtained	obtain	VERB
eurjchem-1645	47	3	crude	crude	NOUN
eurjchem-1645	47	4	was	be	AUX
eurjchem-1645	47	5	diluted	dilute	VERB
eurjchem-1645	47	6	it	it	PRON
eurjchem-1645	47	7	with	with	ADP
eurjchem-1645	47	8	h2o	h2o	PROPN
eurjchem-1645	47	9	(	(	PUNCT
eurjchem-1645	47	10	100	100	NUM
eurjchem-1645	47	11	ml	ml	NOUN
eurjchem-1645	47	12	)	)	PUNCT
eurjchem-1645	47	13	and	and	CCONJ
eurjchem-1645	47	14	extracted	extract	VERB
eurjchem-1645	47	15	it	it	PRON
eurjchem-1645	47	16	with	with	ADP
eurjchem-1645	47	17	etoac	etoac	ADJ
eurjchem-1645	47	18	(	(	PUNCT
eurjchem-1645	47	19	2	2	NUM
eurjchem-1645	47	20	×	×	NOUN
eurjchem-1645	47	21	50	50	NUM
eurjchem-1645	47	22	ml	ml	NOUN
eurjchem-1645	47	23	)	)	PUNCT
eurjchem-1645	47	24	.	.	PUNCT
eurjchem-1645	48	1	the	the	DET
eurjchem-1645	48	2	organic	organic	ADJ
eurjchem-1645	48	3	layer	layer	NOUN
eurjchem-1645	48	4	was	be	AUX
eurjchem-1645	48	5	washed	wash	VERB
eurjchem-1645	48	6	with	with	ADP
eurjchem-1645	48	7	h2o	h2o	PROPN
eurjchem-1645	48	8	(	(	PUNCT
eurjchem-1645	48	9	50	50	NUM
eurjchem-1645	48	10	ml	ml	NOUN
eurjchem-1645	48	11	)	)	PUNCT
eurjchem-1645	48	12	and	and	CCONJ
eurjchem-1645	48	13	brine	brine	NOUN
eurjchem-1645	48	14	(	(	PUNCT
eurjchem-1645	48	15	50	50	NUM
eurjchem-1645	48	16	ml	ml	NOUN
eurjchem-1645	48	17	)	)	PUNCT
eurjchem-1645	48	18	,	,	PUNCT
eurjchem-1645	48	19	dried	dry	VERB
eurjchem-1645	48	20	it	it	PRON
eurjchem-1645	48	21	over	over	ADP
eurjchem-1645	48	22	anhydrous	anhydrous	ADJ
eurjchem-1645	48	23	na2so4	na2so4	NOUN
eurjchem-1645	48	24	to	to	PART
eurjchem-1645	48	25	obtain	obtain	VERB
eurjchem-1645	48	26	yellow	yellow	ADJ
eurjchem-1645	48	27	solid	solid	ADJ
eurjchem-1645	48	28	.	.	PUNCT
eurjchem-1645	49	1	the	the	DET
eurjchem-1645	49	2	crude	crude	ADJ
eurjchem-1645	49	3	material	material	NOUN
eurjchem-1645	49	4	was	be	AUX
eurjchem-1645	49	5	washed	wash	VERB
eurjchem-1645	49	6	with	with	ADP
eurjchem-1645	49	7	10	10	NUM
eurjchem-1645	49	8	%	%	NOUN
eurjchem-1645	49	9	ethyl	ethyl	PROPN
eurjchem-1645	49	10	acetate	acetate	NOUN
eurjchem-1645	49	11	:	:	PUNCT
eurjchem-1645	49	12	hexane	hexane	NOUN
eurjchem-1645	49	13	(	(	PUNCT
eurjchem-1645	49	14	v	v	NOUN
eurjchem-1645	49	15	:	:	PUNCT
eurjchem-1645	49	16	v	v	NOUN
eurjchem-1645	49	17	,	,	PUNCT
eurjchem-1645	49	18	10:90	10:90	NUM
eurjchem-1645	49	19	,	,	PUNCT
eurjchem-1645	49	20	100	100	NUM
eurjchem-1645	49	21	ml	ml	NOUN
eurjchem-1645	49	22	)	)	PUNCT
eurjchem-1645	49	23	,	,	PUNCT
eurjchem-1645	49	24	hexane	hexane	NOUN
eurjchem-1645	49	25	(	(	PUNCT
eurjchem-1645	49	26	100	100	NUM
eurjchem-1645	49	27	ml	ml	NOUN
eurjchem-1645	49	28	)	)	PUNCT
eurjchem-1645	49	29	and	and	CCONJ
eurjchem-1645	49	30	diethyl	diethyl	NOUN
eurjchem-1645	49	31	ether	ether	NOUN
eurjchem-1645	49	32	(	(	PUNCT
eurjchem-1645	49	33	100	100	NUM
eurjchem-1645	49	34	ml	ml	NOUN
eurjchem-1645	49	35	)	)	PUNCT
eurjchem-1645	49	36	to	to	PART
eurjchem-1645	49	37	obtain	obtain	VERB
eurjchem-1645	49	38	compound	compound	NOUN
eurjchem-1645	49	39	2	2	NUM
eurjchem-1645	49	40	.	.	PUNCT
eurjchem-1645	50	1	color	color	NOUN
eurjchem-1645	50	2	:	:	PUNCT
eurjchem-1645	50	3	yellow	yellow	ADJ
eurjchem-1645	50	4	.	.	PUNCT
eurjchem-1645	51	1	yield	yield	NOUN
eurjchem-1645	51	2	:	:	PUNCT
eurjchem-1645	51	3	78	78	NUM
eurjchem-1645	51	4	%	%	NOUN
eurjchem-1645	51	5	(	(	PUNCT
eurjchem-1645	51	6	10.0	10.0	NUM
eurjchem-1645	51	7	g	g	NOUN
eurjchem-1645	51	8	)	)	PUNCT
eurjchem-1645	51	9	.	.	PUNCT
eurjchem-1645	52	1	m.p	m.p	PROPN
eurjchem-1645	52	2	.	.	PROPN
eurjchem-1645	52	3	:	:	PUNCT
eurjchem-1645	52	4	48‐49	48‐49	NUM
eurjchem-1645	52	5	°	°	SYM
eurjchem-1645	52	6	c	c	X
eurjchem-1645	52	7	.	.	PUNCT
eurjchem-1645	53	1	1h	1h	NUM
eurjchem-1645	53	2	nmr	nmr	NOUN
eurjchem-1645	53	3	(	(	PUNCT
eurjchem-1645	53	4	400	400	NUM
eurjchem-1645	53	5	mhz	mhz	NOUN
eurjchem-1645	53	6	,	,	PUNCT
eurjchem-1645	53	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	53	8	,	,	PUNCT
eurjchem-1645	53	9	δ	δ	PROPN
eurjchem-1645	53	10	,	,	PUNCT
eurjchem-1645	53	11	ppm	ppm	NUM
eurjchem-1645	53	12	):	):	PUNCT
eurjchem-1645	53	13	1.41	1.41	NUM
eurjchem-1645	53	14	(	(	PUNCT
eurjchem-1645	53	15	ss	ss	PROPN
eurjchem-1645	53	16	,	,	PUNCT
eurjchem-1645	53	17	9h	9h	NUM
eurjchem-1645	53	18	,	,	PUNCT
eurjchem-1645	53	19	t‐bu	t‐bu	NOUN
eurjchem-1645	53	20	)	)	PUNCT
eurjchem-1645	53	21	,	,	PUNCT
eurjchem-1645	53	22	2.22	2.22	NUM
eurjchem-1645	53	23	(	(	PUNCT
eurjchem-1645	53	24	d	d	PROPN
eurjchem-1645	53	25	,	,	PUNCT
eurjchem-1645	53	26	2h	2h	NUM
eurjchem-1645	53	27	,	,	PUNCT
eurjchem-1645	53	28	j	j	PROPN
eurjchem-1645	53	29	=	=	PROPN
eurjchem-1645	53	30	6.4	6.4	NUM
eurjchem-1645	53	31	hz	hz	NOUN
eurjchem-1645	53	32	,	,	PUNCT
eurjchem-1645	53	33	ch2	ch2	PROPN
eurjchem-1645	53	34	)	)	PUNCT
eurjchem-1645	53	35	,	,	PUNCT
eurjchem-1645	53	36	2.44	2.44	NUM
eurjchem-1645	53	37	(	(	PUNCT
eurjchem-1645	53	38	s	s	PROPN
eurjchem-1645	53	39	,	,	PUNCT
eurjchem-1645	53	40	6h	6h	NUM
eurjchem-1645	53	41	,	,	PUNCT
eurjchem-1645	53	42	n‐(ch3)2	n‐(ch3)2	NOUN
eurjchem-1645	53	43	)	)	PUNCT
eurjchem-1645	53	44	,	,	PUNCT
eurjchem-1645	53	45	2.81	2.81	NUM
eurjchem-1645	53	46	(	(	PUNCT
eurjchem-1645	53	47	m	m	PROPN
eurjchem-1645	53	48	,	,	PUNCT
eurjchem-1645	53	49	2h	2h	NUM
eurjchem-1645	53	50	,	,	PUNCT
eurjchem-1645	53	51	ch2	ch2	PROPN
eurjchem-1645	53	52	)	)	PUNCT
eurjchem-1645	53	53	,	,	PUNCT
eurjchem-1645	53	54	3.81	3.81	NUM
eurjchem-1645	53	55	(	(	PUNCT
eurjchem-1645	53	56	s	s	PROPN
eurjchem-1645	53	57	,	,	PUNCT
eurjchem-1645	53	58	2h	2h	NUM
eurjchem-1645	53	59	,	,	PUNCT
eurjchem-1645	53	60	nh‐ch2	nh‐ch2	NOUN
eurjchem-1645	53	61	)	)	PUNCT
eurjchem-1645	53	62	,	,	PUNCT
eurjchem-1645	53	63	6.89	6.89	NUM
eurjchem-1645	53	64	(	(	PUNCT
eurjchem-1645	53	65	s	s	PROPN
eurjchem-1645	53	66	,	,	PUNCT
eurjchem-1645	53	67	1h	1h	NUM
eurjchem-1645	53	68	,	,	PUNCT
eurjchem-1645	53	69	n‐ch	n‐ch	NOUN
eurjchem-1645	53	70	)	)	PUNCT
eurjchem-1645	53	71	.	.	PUNCT
eurjchem-1645	54	1	13c	13c	NOUN
eurjchem-1645	54	2	nmr	nmr	NOUN
eurjchem-1645	54	3	(	(	PUNCT
eurjchem-1645	54	4	100	100	NUM
eurjchem-1645	54	5	mhz	mhz	NOUN
eurjchem-1645	54	6	,	,	PUNCT
eurjchem-1645	54	7	cdcl3	cdcl3	PROPN
eurjchem-1645	54	8	,	,	PUNCT
eurjchem-1645	54	9	δ	δ	PROPN
eurjchem-1645	54	10	,	,	PUNCT
eurjchem-1645	54	11	ppm	ppm	NOUN
eurjchem-1645	54	12	):	):	PUNCT
eurjchem-1645	54	13	28.55	28.55	NUM
eurjchem-1645	54	14	,	,	PUNCT
eurjchem-1645	54	15	30.32	30.32	NUM
eurjchem-1645	54	16	,	,	PUNCT
eurjchem-1645	54	17	43.47	43.47	NUM
eurjchem-1645	54	18	,	,	PUNCT
eurjchem-1645	54	19	47.46	47.46	NUM
eurjchem-1645	54	20	,	,	PUNCT
eurjchem-1645	54	21	58.89	58.89	NUM
eurjchem-1645	54	22	,	,	PUNCT
eurjchem-1645	54	23	81.2	81.2	NUM
eurjchem-1645	54	24	,	,	PUNCT
eurjchem-1645	54	25	101.21	101.21	NUM
eurjchem-1645	54	26	,	,	PUNCT
eurjchem-1645	54	27	146.12	146.12	NUM
eurjchem-1645	54	28	,	,	PUNCT
eurjchem-1645	54	29	154.42	154.42	NUM
eurjchem-1645	54	30	,	,	PUNCT
eurjchem-1645	54	31	192.22	192.22	NUM
eurjchem-1645	54	32	.	.	PUNCT
eurjchem-1645	55	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	55	2	(	(	PUNCT
eurjchem-1645	55	3	ei	ei	PROPN
eurjchem-1645	55	4	,	,	PUNCT
eurjchem-1645	55	5	m	m	PROPN
eurjchem-1645	55	6	/	/	SYM
eurjchem-1645	55	7	z	z	NOUN
eurjchem-1645	55	8	):	):	PUNCT
eurjchem-1645	55	9	255	255	NUM
eurjchem-1645	55	10	(	(	PUNCT
eurjchem-1645	55	11	m+h	m+h	NOUN
eurjchem-1645	55	12	)	)	PUNCT
eurjchem-1645	55	13	.	.	PUNCT
eurjchem-1645	56	1	anal	anal	PROPN
eurjchem-1645	56	2	.	.	PUNCT
eurjchem-1645	56	3	calcd	calcd	NOUN
eurjchem-1645	56	4	.	.	PUNCT
eurjchem-1645	57	1	for	for	ADP
eurjchem-1645	57	2	c13h22n2o3	c13h22n2o3	NOUN
eurjchem-1645	57	3	:	:	PUNCT
eurjchem-1645	57	4	c	c	NOUN
eurjchem-1645	57	5	,	,	PUNCT
eurjchem-1645	57	6	61.39	61.39	NUM
eurjchem-1645	57	7	;	;	PUNCT
eurjchem-1645	57	8	h	h	NOUN
eurjchem-1645	57	9	,	,	PUNCT
eurjchem-1645	57	10	8.72	8.72	NUM
eurjchem-1645	57	11	;	;	PUNCT
eurjchem-1645	57	12	n	n	CCONJ
eurjchem-1645	57	13	,	,	PUNCT
eurjchem-1645	57	14	11.01	11.01	NUM
eurjchem-1645	57	15	.	.	PUNCT
eurjchem-1645	57	16	found	find	VERB
eurjchem-1645	57	17	:	:	PUNCT
eurjchem-1645	58	1	c	c	X
eurjchem-1645	58	2	,	,	PUNCT
eurjchem-1645	58	3	61.36	61.36	NUM
eurjchem-1645	58	4	;	;	PUNCT
eurjchem-1645	58	5	h	h	NOUN
eurjchem-1645	58	6	,	,	PUNCT
eurjchem-1645	58	7	8.73	8.73	NUM
eurjchem-1645	58	8	;	;	PUNCT
eurjchem-1645	58	9	n	n	CCONJ
eurjchem-1645	58	10	,	,	PUNCT
eurjchem-1645	58	11	11.03	11.03	NUM
eurjchem-1645	58	12	%	%	NOUN
eurjchem-1645	58	13	.	.	PUNCT
eurjchem-1645	59	1	2.2.2	2.2.2	X
eurjchem-1645	59	2	.	.	X
eurjchem-1645	60	1	synthesis	synthesis	NOUN
eurjchem-1645	60	2	of	of	ADP
eurjchem-1645	60	3	4,5,6,7‐tetrahydro‐1h‐pyrazolo[4,3‐c	4,5,6,7‐tetrahydro‐1h‐pyrazolo[4,3‐c	NUM
eurjchem-1645	60	4	]	]	X
eurjchem-1645	60	5	pyridine	pyridine	NOUN
eurjchem-1645	60	6	(	(	PUNCT
eurjchem-1645	60	7	3	3	NUM
eurjchem-1645	60	8	)	)	PUNCT
eurjchem-1645	60	9	,	,	PUNCT
eurjchem-1645	60	10	step	step	NOUN
eurjchem-1645	60	11	(	(	PUNCT
eurjchem-1645	60	12	b	b	NOUN
eurjchem-1645	60	13	)	)	PUNCT
eurjchem-1645	60	14	to	to	ADP
eurjchem-1645	60	15	a	a	DET
eurjchem-1645	60	16	stirred	stir	VERB
eurjchem-1645	60	17	solution	solution	NOUN
eurjchem-1645	60	18	of	of	ADP
eurjchem-1645	60	19	compound	compound	NOUN
eurjchem-1645	60	20	2	2	NUM
eurjchem-1645	60	21	(	(	PUNCT
eurjchem-1645	60	22	10.0	10.0	NUM
eurjchem-1645	60	23	g	g	NOUN
eurjchem-1645	60	24	,	,	PUNCT
eurjchem-1645	60	25	39.4	39.4	NUM
eurjchem-1645	60	26	mmol	mmol	NOUN
eurjchem-1645	60	27	)	)	PUNCT
eurjchem-1645	60	28	was	be	AUX
eurjchem-1645	60	29	dissolved	dissolve	VERB
eurjchem-1645	60	30	in	in	ADP
eurjchem-1645	60	31	ethanol	ethanol	NOUN
eurjchem-1645	60	32	(	(	PUNCT
eurjchem-1645	60	33	50	50	NUM
eurjchem-1645	60	34	ml	ml	NOUN
eurjchem-1645	60	35	)	)	PUNCT
eurjchem-1645	60	36	and	and	CCONJ
eurjchem-1645	60	37	hydrazine	hydrazine	NOUN
eurjchem-1645	60	38	hydrate	hydrate	NOUN
eurjchem-1645	60	39	(	(	PUNCT
eurjchem-1645	60	40	3.94	3.94	NUM
eurjchem-1645	60	41	g	g	NOUN
eurjchem-1645	60	42	,	,	PUNCT
eurjchem-1645	60	43	78.7	78.7	NUM
eurjchem-1645	60	44	mmol	mmol	NOUN
eurjchem-1645	60	45	)	)	PUNCT
eurjchem-1645	60	46	.	.	PUNCT
eurjchem-1645	61	1	the	the	DET
eurjchem-1645	61	2	reaction	reaction	NOUN
eurjchem-1645	61	3	mixture	mixture	NOUN
eurjchem-1645	61	4	was	be	AUX
eurjchem-1645	61	5	heated	heat	VERB
eurjchem-1645	61	6	at	at	ADP
eurjchem-1645	61	7	80	80	NUM
eurjchem-1645	61	8	°	°	NUM
eurjchem-1645	61	9	c	c	NOUN
eurjchem-1645	61	10	for	for	ADP
eurjchem-1645	61	11	8	8	NUM
eurjchem-1645	61	12	h	h	NOUN
eurjchem-1645	61	13	and	and	CCONJ
eurjchem-1645	61	14	the	the	DET
eurjchem-1645	61	15	progress	progress	NOUN
eurjchem-1645	61	16	of	of	ADP
eurjchem-1645	61	17	reaction	reaction	NOUN
eurjchem-1645	61	18	was	be	AUX
eurjchem-1645	61	19	monitored	monitor	VERB
eurjchem-1645	61	20	by	by	ADP
eurjchem-1645	61	21	lc‐ms	lc‐ms	PRON
eurjchem-1645	61	22	for	for	ADP
eurjchem-1645	61	23	the	the	DET
eurjchem-1645	61	24	consumption	consumption	NOUN
eurjchem-1645	61	25	of	of	ADP
eurjchem-1645	61	26	starting	start	VERB
eurjchem-1645	61	27	material	material	NOUN
eurjchem-1645	61	28	.	.	PUNCT
eurjchem-1645	62	1	402	402	NUM
eurjchem-1645	62	2	pawar	pawar	PROPN
eurjchem-1645	62	3	et	et	PROPN
eurjchem-1645	62	4	al	al	PROPN
eurjchem-1645	62	5	.	.	PUNCT
eurjchem-1645	62	6	/	/	SYM
eurjchem-1645	62	7	european	european	PROPN
eurjchem-1645	62	8	journal	journal	PROPN
eurjchem-1645	62	9	of	of	ADP
eurjchem-1645	62	10	chemistry	chemistry	NOUN
eurjchem-1645	62	11	8	8	NUM
eurjchem-1645	62	12	(	(	PUNCT
eurjchem-1645	62	13	4	4	NUM
eurjchem-1645	62	14	)	)	PUNCT
eurjchem-1645	62	15	(	(	PUNCT
eurjchem-1645	62	16	2017	2017	NUM
eurjchem-1645	62	17	)	)	PUNCT
eurjchem-1645	62	18	400‐409	400‐409	NUM
eurjchem-1645	62	19	reagents	reagent	NOUN
eurjchem-1645	62	20	and	and	CCONJ
eurjchem-1645	62	21	conditions	condition	NOUN
eurjchem-1645	62	22	:	:	PUNCT
eurjchem-1645	62	23	(	(	PUNCT
eurjchem-1645	62	24	a	a	X
eurjchem-1645	62	25	)	)	PUNCT
eurjchem-1645	62	26	kmno4	kmno4	PROPN
eurjchem-1645	62	27	,	,	PUNCT
eurjchem-1645	62	28	18‐crown‐6	18‐crown‐6	NUM
eurjchem-1645	62	29	,	,	PUNCT
eurjchem-1645	62	30	dcm	dcm	PROPN
eurjchem-1645	62	31	,	,	PUNCT
eurjchem-1645	62	32	room	room	NOUN
eurjchem-1645	62	33	temperature	temperature	NOUN
eurjchem-1645	62	34	,	,	PUNCT
eurjchem-1645	62	35	6	6	NUM
eurjchem-1645	62	36	h	h	NOUN
eurjchem-1645	62	37	,	,	PUNCT
eurjchem-1645	62	38	(	(	PUNCT
eurjchem-1645	62	39	general	general	ADJ
eurjchem-1645	62	40	procedure	procedure	NOUN
eurjchem-1645	62	41	)	)	PUNCT
eurjchem-1645	62	42	;	;	PUNCT
eurjchem-1645	62	43	(	(	PUNCT
eurjchem-1645	62	44	b	b	X
eurjchem-1645	62	45	)	)	PUNCT
eurjchem-1645	62	46	6	6	NUM
eurjchem-1645	62	47	n	n	PRON
eurjchem-1645	62	48	hcl	hcl	PROPN
eurjchem-1645	62	49	,	,	PUNCT
eurjchem-1645	62	50	room	room	NOUN
eurjchem-1645	62	51	temperature	temperature	NOUN
eurjchem-1645	62	52	,	,	PUNCT
eurjchem-1645	62	53	6	6	NUM
eurjchem-1645	62	54	h	h	NOUN
eurjchem-1645	62	55	(	(	PUNCT
eurjchem-1645	62	56	general	general	ADJ
eurjchem-1645	62	57	procedure	procedure	NOUN
eurjchem-1645	62	58	)	)	PUNCT
eurjchem-1645	62	59	.	.	PUNCT
eurjchem-1645	63	1	scheme	scheme	NOUN
eurjchem-1645	63	2	2	2	NUM
eurjchem-1645	63	3	the	the	DET
eurjchem-1645	63	4	reaction	reaction	NOUN
eurjchem-1645	63	5	mixture	mixture	NOUN
eurjchem-1645	63	6	was	be	AUX
eurjchem-1645	63	7	cooled	cool	VERB
eurjchem-1645	63	8	to	to	ADP
eurjchem-1645	63	9	room	room	NOUN
eurjchem-1645	63	10	temperature	temperature	NOUN
eurjchem-1645	63	11	and	and	CCONJ
eurjchem-1645	63	12	evaporated	evaporate	VERB
eurjchem-1645	63	13	under	under	ADP
eurjchem-1645	63	14	reduced	reduce	VERB
eurjchem-1645	63	15	pressure	pressure	NOUN
eurjchem-1645	63	16	to	to	PART
eurjchem-1645	63	17	obtain	obtain	VERB
eurjchem-1645	63	18	yellow	yellow	ADJ
eurjchem-1645	63	19	gummy	gummy	ADJ
eurjchem-1645	63	20	material	material	NOUN
eurjchem-1645	63	21	.	.	PUNCT
eurjchem-1645	64	1	the	the	DET
eurjchem-1645	64	2	obtained	obtain	VERB
eurjchem-1645	64	3	crude	crude	ADJ
eurjchem-1645	64	4	material	material	NOUN
eurjchem-1645	64	5	was	be	AUX
eurjchem-1645	64	6	purified	purify	VERB
eurjchem-1645	64	7	by	by	ADP
eurjchem-1645	64	8	silica	silica	NOUN
eurjchem-1645	64	9	gel	gel	NOUN
eurjchem-1645	64	10	(	(	PUNCT
eurjchem-1645	64	11	100‐200	100‐200	NUM
eurjchem-1645	64	12	mesh	mesh	NOUN
eurjchem-1645	64	13	)	)	PUNCT
eurjchem-1645	64	14	column	column	NOUN
eurjchem-1645	64	15	chromatography	chromatography	NOUN
eurjchem-1645	64	16	by	by	ADP
eurjchem-1645	64	17	using	use	VERB
eurjchem-1645	64	18	10‐40	10‐40	NUM
eurjchem-1645	64	19	%	%	PROPN
eurjchem-1645	64	20	ethyl	ethyl	PROPN
eurjchem-1645	64	21	acetate	acetate	NOUN
eurjchem-1645	64	22	:	:	PUNCT
eurjchem-1645	64	23	hexane	hexane	NOUN
eurjchem-1645	64	24	(	(	PUNCT
eurjchem-1645	64	25	v	v	NOUN
eurjchem-1645	64	26	:	:	PUNCT
eurjchem-1645	64	27	v	v	NOUN
eurjchem-1645	64	28	,	,	PUNCT
eurjchem-1645	64	29	10‐40:90‐60	10‐40:90‐60	NUM
eurjchem-1645	64	30	)	)	PUNCT
eurjchem-1645	64	31	.	.	PUNCT
eurjchem-1645	65	1	the	the	DET
eurjchem-1645	65	2	obtained	obtain	VERB
eurjchem-1645	65	3	compound	compound	NOUN
eurjchem-1645	65	4	was	be	AUX
eurjchem-1645	65	5	washed	wash	VERB
eurjchem-1645	65	6	with	with	ADP
eurjchem-1645	65	7	diethyl	diethyl	NOUN
eurjchem-1645	65	8	ether	ether	NOUN
eurjchem-1645	65	9	(	(	PUNCT
eurjchem-1645	65	10	100	100	NUM
eurjchem-1645	65	11	ml	ml	NOUN
eurjchem-1645	65	12	)	)	PUNCT
eurjchem-1645	65	13	to	to	PART
eurjchem-1645	65	14	obtain	obtain	VERB
eurjchem-1645	65	15	compound	compound	NOUN
eurjchem-1645	65	16	3	3	NUM
eurjchem-1645	65	17	[	[	X
eurjchem-1645	65	18	13	13	NUM
eurjchem-1645	65	19	]	]	PUNCT
eurjchem-1645	65	20	.	.	PUNCT
eurjchem-1645	66	1	color	color	NOUN
eurjchem-1645	66	2	:	:	PUNCT
eurjchem-1645	66	3	yellow	yellow	ADJ
eurjchem-1645	66	4	.	.	PUNCT
eurjchem-1645	67	1	yield	yield	NOUN
eurjchem-1645	67	2	:	:	PUNCT
eurjchem-1645	67	3	68.3	68.3	NUM
eurjchem-1645	67	4	%	%	NOUN
eurjchem-1645	67	5	,	,	PUNCT
eurjchem-1645	67	6	6	6	NUM
eurjchem-1645	67	7	g.	g.	NOUN
eurjchem-1645	67	8	m.p	m.p	PROPN
eurjchem-1645	67	9	.	.	PROPN
eurjchem-1645	67	10	:	:	PUNCT
eurjchem-1645	67	11	74‐75	74‐75	NUM
eurjchem-1645	67	12	°	°	PROPN
eurjchem-1645	67	13	c	c	PROPN
eurjchem-1645	67	14	.	.	PUNCT
eurjchem-1645	68	1	1h	1h	NUM
eurjchem-1645	68	2	nmr	nmr	NOUN
eurjchem-1645	68	3	(	(	PUNCT
eurjchem-1645	68	4	400	400	NUM
eurjchem-1645	68	5	mhz	mhz	NOUN
eurjchem-1645	68	6	,	,	PUNCT
eurjchem-1645	68	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	68	8	,	,	PUNCT
eurjchem-1645	68	9	δ	δ	PROPN
eurjchem-1645	68	10	,	,	PUNCT
eurjchem-1645	68	11	ppm	ppm	NOUN
eurjchem-1645	68	12	):	):	PUNCT
eurjchem-1645	68	13	1.46	1.46	NUM
eurjchem-1645	68	14	(	(	PUNCT
eurjchem-1645	68	15	s	s	PROPN
eurjchem-1645	68	16	,	,	PUNCT
eurjchem-1645	68	17	9h	9h	NUM
eurjchem-1645	68	18	,	,	PUNCT
eurjchem-1645	68	19	t‐bu	t‐bu	NOUN
eurjchem-1645	68	20	)	)	PUNCT
eurjchem-1645	68	21	,	,	PUNCT
eurjchem-1645	68	22	2.22	2.22	NUM
eurjchem-1645	68	23	(	(	PUNCT
eurjchem-1645	68	24	d	d	PROPN
eurjchem-1645	68	25	,	,	PUNCT
eurjchem-1645	68	26	2h	2h	NUM
eurjchem-1645	68	27	,	,	PUNCT
eurjchem-1645	68	28	j	j	PROPN
eurjchem-1645	68	29	=	=	PROPN
eurjchem-1645	68	30	6.4	6.4	NUM
eurjchem-1645	68	31	hz	hz	NOUN
eurjchem-1645	68	32	,	,	PUNCT
eurjchem-1645	68	33	ch2	ch2	PROPN
eurjchem-1645	68	34	)	)	PUNCT
eurjchem-1645	68	35	,	,	PUNCT
eurjchem-1645	68	36	2.80	2.80	NUM
eurjchem-1645	68	37	(	(	PUNCT
eurjchem-1645	68	38	m	m	PROPN
eurjchem-1645	68	39	,	,	PUNCT
eurjchem-1645	68	40	2h	2h	NUM
eurjchem-1645	68	41	,	,	PUNCT
eurjchem-1645	68	42	ch2	ch2	PROPN
eurjchem-1645	68	43	)	)	PUNCT
eurjchem-1645	68	44	,	,	PUNCT
eurjchem-1645	68	45	3.84	3.84	NUM
eurjchem-1645	68	46	(	(	PUNCT
eurjchem-1645	68	47	s	s	PROPN
eurjchem-1645	68	48	,	,	PUNCT
eurjchem-1645	68	49	2h	2h	NUM
eurjchem-1645	68	50	,	,	PUNCT
eurjchem-1645	68	51	nh‐	nh‐	ADJ
eurjchem-1645	68	52	ch2	ch2	NOUN
eurjchem-1645	68	53	)	)	PUNCT
eurjchem-1645	68	54	,	,	PUNCT
eurjchem-1645	68	55	7.31	7.31	NUM
eurjchem-1645	68	56	(	(	PUNCT
eurjchem-1645	68	57	s	s	PROPN
eurjchem-1645	68	58	,	,	PUNCT
eurjchem-1645	68	59	1h	1h	NUM
eurjchem-1645	68	60	,	,	PUNCT
eurjchem-1645	68	61	ar‐h	ar‐h	NOUN
eurjchem-1645	68	62	)	)	PUNCT
eurjchem-1645	68	63	,	,	PUNCT
eurjchem-1645	68	64	12.6	12.6	NUM
eurjchem-1645	68	65	(	(	PUNCT
eurjchem-1645	68	66	br	br	PROPN
eurjchem-1645	68	67	,	,	PUNCT
eurjchem-1645	68	68	1h	1h	NUM
eurjchem-1645	68	69	,	,	PUNCT
eurjchem-1645	68	70	ar‐nh	ar‐nh	NOUN
eurjchem-1645	68	71	)	)	PUNCT
eurjchem-1645	68	72	.	.	PUNCT
eurjchem-1645	69	1	13c	13c	NOUN
eurjchem-1645	69	2	nmr	nmr	NOUN
eurjchem-1645	69	3	(	(	PUNCT
eurjchem-1645	69	4	100	100	NUM
eurjchem-1645	69	5	mhz	mhz	NOUN
eurjchem-1645	69	6	,	,	PUNCT
eurjchem-1645	69	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	69	8	,	,	PUNCT
eurjchem-1645	69	9	δ	δ	PROPN
eurjchem-1645	69	10	,	,	PUNCT
eurjchem-1645	69	11	ppm	ppm	NOUN
eurjchem-1645	69	12	):	):	PUNCT
eurjchem-1645	69	13	19.21	19.21	NUM
eurjchem-1645	69	14	,	,	PUNCT
eurjchem-1645	69	15	28.88	28.88	NUM
eurjchem-1645	69	16	,	,	PUNCT
eurjchem-1645	69	17	38.41	38.41	NUM
eurjchem-1645	69	18	,	,	PUNCT
eurjchem-1645	69	19	47.11	47.11	NUM
eurjchem-1645	69	20	,	,	PUNCT
eurjchem-1645	69	21	80.2	80.2	NUM
eurjchem-1645	69	22	,	,	PUNCT
eurjchem-1645	69	23	114.12	114.12	NUM
eurjchem-1645	69	24	,	,	PUNCT
eurjchem-1645	69	25	133.57	133.57	NUM
eurjchem-1645	69	26	,	,	PUNCT
eurjchem-1645	69	27	142.26	142.26	NUM
eurjchem-1645	69	28	,	,	PUNCT
eurjchem-1645	69	29	152.88	152.88	NUM
eurjchem-1645	69	30	.	.	PUNCT
eurjchem-1645	70	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	70	2	(	(	PUNCT
eurjchem-1645	70	3	ei	ei	PROPN
eurjchem-1645	70	4	,	,	PUNCT
eurjchem-1645	70	5	m	m	PROPN
eurjchem-1645	70	6	/	/	SYM
eurjchem-1645	70	7	z	z	NOUN
eurjchem-1645	70	8	):	):	PUNCT
eurjchem-1645	70	9	225	225	NUM
eurjchem-1645	70	10	(	(	PUNCT
eurjchem-1645	70	11	m+h	m+h	NOUN
eurjchem-1645	70	12	)	)	PUNCT
eurjchem-1645	70	13	.	.	PUNCT
eurjchem-1645	71	1	anal	anal	PROPN
eurjchem-1645	71	2	.	.	PUNCT
eurjchem-1645	71	3	calcd	calcd	NOUN
eurjchem-1645	71	4	.	.	PUNCT
eurjchem-1645	72	1	for	for	ADP
eurjchem-1645	72	2	c11h17n3o2	c11h17n3o2	PROPN
eurjchem-1645	72	3	:	:	PUNCT
eurjchem-1645	72	4	c	c	X
eurjchem-1645	72	5	,	,	PUNCT
eurjchem-1645	72	6	59.17	59.17	NUM
eurjchem-1645	72	7	;	;	PUNCT
eurjchem-1645	72	8	h	h	NOUN
eurjchem-1645	72	9	,	,	PUNCT
eurjchem-1645	72	10	7.67	7.67	NUM
eurjchem-1645	72	11	;	;	PUNCT
eurjchem-1645	72	12	n	n	CCONJ
eurjchem-1645	72	13	,	,	PUNCT
eurjchem-1645	72	14	18.82	18.82	NUM
eurjchem-1645	72	15	.	.	PUNCT
eurjchem-1645	72	16	found	find	VERB
eurjchem-1645	72	17	:	:	PUNCT
eurjchem-1645	73	1	c	c	X
eurjchem-1645	73	2	,	,	PUNCT
eurjchem-1645	73	3	59.14	59.14	NUM
eurjchem-1645	73	4	;	;	PUNCT
eurjchem-1645	73	5	h	h	X
eurjchem-1645	73	6	,	,	PUNCT
eurjchem-1645	73	7	7.68	7.68	NUM
eurjchem-1645	73	8	;	;	PUNCT
eurjchem-1645	73	9	n	n	CCONJ
eurjchem-1645	73	10	,	,	PUNCT
eurjchem-1645	73	11	18.80	18.80	NUM
eurjchem-1645	73	12	%	%	NOUN
eurjchem-1645	73	13	.	.	PUNCT
eurjchem-1645	74	1	2.2.3	2.2.3	X
eurjchem-1645	74	2	.	.	X
eurjchem-1645	75	1	synthesis	synthesis	NOUN
eurjchem-1645	75	2	of	of	ADP
eurjchem-1645	75	3	di‐tert‐butyl	di‐tert‐butyl	PROPN
eurjchem-1645	75	4	4,5‐dihydro‐7h‐pyrazolo	4,5‐dihydro‐7h‐pyrazolo	NOUN
eurjchem-1645	76	1	[	[	X
eurjchem-1645	76	2	3,4‐c]pyridine‐1,6‐dicarboxylate	3,4‐c]pyridine‐1,6‐dicarboxylate	NUM
eurjchem-1645	76	3	(	(	PUNCT
eurjchem-1645	76	4	4	4	NUM
eurjchem-1645	76	5	)	)	PUNCT
eurjchem-1645	76	6	,	,	PUNCT
eurjchem-1645	76	7	step	step	NOUN
eurjchem-1645	76	8	(	(	PUNCT
eurjchem-1645	76	9	c	c	NOUN
eurjchem-1645	76	10	)	)	PUNCT
eurjchem-1645	76	11	to	to	ADP
eurjchem-1645	76	12	a	a	DET
eurjchem-1645	76	13	stirred	stir	VERB
eurjchem-1645	76	14	solution	solution	NOUN
eurjchem-1645	76	15	of	of	ADP
eurjchem-1645	76	16	compound	compound	NOUN
eurjchem-1645	76	17	3	3	NUM
eurjchem-1645	76	18	(	(	PUNCT
eurjchem-1645	76	19	5.00	5.00	NUM
eurjchem-1645	76	20	g	g	NOUN
eurjchem-1645	76	21	,	,	PUNCT
eurjchem-1645	76	22	22.4	22.4	NUM
eurjchem-1645	76	23	mmol	mmol	NOUN
eurjchem-1645	76	24	)	)	PUNCT
eurjchem-1645	76	25	in	in	ADP
eurjchem-1645	76	26	dcm	dcm	PROPN
eurjchem-1645	76	27	(	(	PUNCT
eurjchem-1645	76	28	50	50	NUM
eurjchem-1645	76	29	ml	ml	NOUN
eurjchem-1645	76	30	)	)	PUNCT
eurjchem-1645	76	31	,	,	PUNCT
eurjchem-1645	76	32	triethylamine	triethylamine	NOUN
eurjchem-1645	76	33	(	(	PUNCT
eurjchem-1645	76	34	6.00	6.00	NUM
eurjchem-1645	76	35	ml	ml	NOUN
eurjchem-1645	76	36	,	,	PUNCT
eurjchem-1645	76	37	44.8	44.8	NUM
eurjchem-1645	76	38	mmol	mmol	NOUN
eurjchem-1645	76	39	)	)	PUNCT
eurjchem-1645	76	40	was	be	AUX
eurjchem-1645	76	41	added	add	VERB
eurjchem-1645	76	42	boc	boc	NOUN
eurjchem-1645	76	43	anhydride	anhydride	NOUN
eurjchem-1645	76	44	(	(	PUNCT
eurjchem-1645	76	45	7.33	7.33	NUM
eurjchem-1645	76	46	g	g	NOUN
eurjchem-1645	76	47	,	,	PUNCT
eurjchem-1645	76	48	33.6	33.6	NUM
eurjchem-1645	76	49	mmol	mmol	NOUN
eurjchem-1645	76	50	)	)	PUNCT
eurjchem-1645	76	51	and	and	CCONJ
eurjchem-1645	76	52	stirred	stir	VERB
eurjchem-1645	76	53	reaction	reaction	NOUN
eurjchem-1645	76	54	mixture	mixture	NOUN
eurjchem-1645	76	55	to	to	PART
eurjchem-1645	76	56	room	room	VERB
eurjchem-1645	76	57	temperature	temperature	NOUN
eurjchem-1645	76	58	for	for	ADP
eurjchem-1645	76	59	3	3	NUM
eurjchem-1645	76	60	h.	h.	NOUN
eurjchem-1645	76	61	progress	progress	NOUN
eurjchem-1645	76	62	of	of	ADP
eurjchem-1645	76	63	reaction	reaction	NOUN
eurjchem-1645	76	64	was	be	AUX
eurjchem-1645	76	65	monitored	monitor	VERB
eurjchem-1645	76	66	by	by	ADP
eurjchem-1645	76	67	lc‐ms	lc‐ms	PRON
eurjchem-1645	76	68	for	for	ADP
eurjchem-1645	76	69	the	the	DET
eurjchem-1645	76	70	consumption	consumption	NOUN
eurjchem-1645	76	71	of	of	ADP
eurjchem-1645	76	72	starting	start	VERB
eurjchem-1645	76	73	material	material	NOUN
eurjchem-1645	76	74	.	.	PUNCT
eurjchem-1645	77	1	after	after	ADP
eurjchem-1645	77	2	completion	completion	NOUN
eurjchem-1645	77	3	the	the	DET
eurjchem-1645	77	4	reaction	reaction	NOUN
eurjchem-1645	77	5	,	,	PUNCT
eurjchem-1645	77	6	the	the	DET
eurjchem-1645	77	7	reaction	reaction	NOUN
eurjchem-1645	77	8	mixture	mixture	NOUN
eurjchem-1645	77	9	evaporated	evaporate	VERB
eurjchem-1645	77	10	under	under	ADP
eurjchem-1645	77	11	reduced	reduced	ADJ
eurjchem-1645	77	12	pressure	pressure	NOUN
eurjchem-1645	77	13	to	to	PART
eurjchem-1645	77	14	obtain	obtain	VERB
eurjchem-1645	77	15	yellow	yellow	ADJ
eurjchem-1645	77	16	gummy	gummy	ADJ
eurjchem-1645	77	17	material	material	NOUN
eurjchem-1645	77	18	.	.	PUNCT
eurjchem-1645	78	1	the	the	DET
eurjchem-1645	78	2	obtained	obtain	VERB
eurjchem-1645	78	3	crude	crude	NOUN
eurjchem-1645	78	4	was	be	AUX
eurjchem-1645	78	5	washed	wash	VERB
eurjchem-1645	78	6	with	with	ADP
eurjchem-1645	78	7	10	10	NUM
eurjchem-1645	78	8	%	%	NOUN
eurjchem-1645	78	9	ethyl	ethyl	PROPN
eurjchem-1645	78	10	acetate	acetate	NOUN
eurjchem-1645	78	11	:	:	PUNCT
eurjchem-1645	78	12	hexane	hexane	NOUN
eurjchem-1645	78	13	(	(	PUNCT
eurjchem-1645	78	14	v	v	NOUN
eurjchem-1645	78	15	:	:	PUNCT
eurjchem-1645	78	16	v	v	NOUN
eurjchem-1645	78	17	,	,	PUNCT
eurjchem-1645	78	18	10:90	10:90	NUM
eurjchem-1645	78	19	)	)	PUNCT
eurjchem-1645	78	20	(	(	PUNCT
eurjchem-1645	78	21	25	25	NUM
eurjchem-1645	78	22	ml	ml	NOUN
eurjchem-1645	78	23	)	)	PUNCT
eurjchem-1645	78	24	,	,	PUNCT
eurjchem-1645	78	25	hexane	hexane	NOUN
eurjchem-1645	78	26	(	(	PUNCT
eurjchem-1645	78	27	50	50	NUM
eurjchem-1645	78	28	ml	ml	NOUN
eurjchem-1645	78	29	)	)	PUNCT
eurjchem-1645	78	30	and	and	CCONJ
eurjchem-1645	78	31	diethyl	diethyl	NOUN
eurjchem-1645	78	32	ether	ether	NOUN
eurjchem-1645	78	33	(	(	PUNCT
eurjchem-1645	78	34	50	50	NUM
eurjchem-1645	78	35	ml	ml	NOUN
eurjchem-1645	78	36	)	)	PUNCT
eurjchem-1645	78	37	to	to	PART
eurjchem-1645	78	38	obtain	obtain	VERB
eurjchem-1645	78	39	compound	compound	NOUN
eurjchem-1645	78	40	4	4	NUM
eurjchem-1645	78	41	.	.	PUNCT
eurjchem-1645	79	1	color	color	NOUN
eurjchem-1645	79	2	:	:	PUNCT
eurjchem-1645	79	3	yellow	yellow	ADJ
eurjchem-1645	79	4	.	.	PUNCT
eurjchem-1645	80	1	yield	yield	NOUN
eurjchem-1645	80	2	:	:	PUNCT
eurjchem-1645	80	3	91	91	NUM
eurjchem-1645	80	4	%	%	NOUN
eurjchem-1645	80	5	,	,	PUNCT
eurjchem-1645	80	6	6.6	6.6	NUM
eurjchem-1645	80	7	g.	g.	NOUN
eurjchem-1645	80	8	m.p	m.p	PROPN
eurjchem-1645	80	9	.	.	PROPN
eurjchem-1645	80	10	:	:	PUNCT
eurjchem-1645	81	1	55‐56	55‐56	NUM
eurjchem-1645	81	2	°	°	PRON
eurjchem-1645	81	3	c	c	NOUN
eurjchem-1645	81	4	.	.	PUNCT
eurjchem-1645	82	1	1h	1h	NUM
eurjchem-1645	82	2	nmr	nmr	NOUN
eurjchem-1645	82	3	(	(	PUNCT
eurjchem-1645	82	4	400	400	NUM
eurjchem-1645	82	5	mhz	mhz	NOUN
eurjchem-1645	82	6	,	,	PUNCT
eurjchem-1645	82	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	82	8	,	,	PUNCT
eurjchem-1645	82	9	δ	δ	PROPN
eurjchem-1645	82	10	,	,	PUNCT
eurjchem-1645	82	11	ppm	ppm	NUM
eurjchem-1645	82	12	):	):	PUNCT
eurjchem-1645	82	13	1.56	1.56	NUM
eurjchem-1645	82	14	(	(	PUNCT
eurjchem-1645	82	15	s	s	PROPN
eurjchem-1645	82	16	,	,	PUNCT
eurjchem-1645	82	17	18h	18h	NOUN
eurjchem-1645	82	18	,	,	PUNCT
eurjchem-1645	82	19	n‐(t‐bu)2	n‐(t‐bu)2	PROPN
eurjchem-1645	82	20	)	)	PUNCT
eurjchem-1645	82	21	,	,	PUNCT
eurjchem-1645	82	22	2.21	2.21	NUM
eurjchem-1645	82	23	(	(	PUNCT
eurjchem-1645	82	24	d	d	PROPN
eurjchem-1645	82	25	,	,	PUNCT
eurjchem-1645	82	26	2h	2h	NUM
eurjchem-1645	82	27	,	,	PUNCT
eurjchem-1645	82	28	j	j	PROPN
eurjchem-1645	82	29	=	=	SYM
eurjchem-1645	82	30	6.2	6.2	NUM
eurjchem-1645	82	31	hz	hz	NOUN
eurjchem-1645	82	32	,	,	PUNCT
eurjchem-1645	82	33	ch2	ch2	PROPN
eurjchem-1645	82	34	)	)	PUNCT
eurjchem-1645	82	35	,	,	PUNCT
eurjchem-1645	82	36	2.79	2.79	NUM
eurjchem-1645	82	37	(	(	PUNCT
eurjchem-1645	82	38	m	m	PROPN
eurjchem-1645	82	39	,	,	PUNCT
eurjchem-1645	82	40	2h	2h	NUM
eurjchem-1645	82	41	,	,	PUNCT
eurjchem-1645	82	42	ch2	ch2	PROPN
eurjchem-1645	82	43	)	)	PUNCT
eurjchem-1645	82	44	,	,	PUNCT
eurjchem-1645	82	45	3.83	3.83	NUM
eurjchem-1645	82	46	(	(	PUNCT
eurjchem-1645	82	47	s	s	PROPN
eurjchem-1645	82	48	,	,	PUNCT
eurjchem-1645	82	49	2h	2h	NUM
eurjchem-1645	82	50	,	,	PUNCT
eurjchem-1645	82	51	n‐ch2	n‐ch2	PROPN
eurjchem-1645	82	52	)	)	PUNCT
eurjchem-1645	82	53	,	,	PUNCT
eurjchem-1645	82	54	7.31	7.31	NUM
eurjchem-1645	82	55	(	(	PUNCT
eurjchem-1645	82	56	s	s	PROPN
eurjchem-1645	82	57	,	,	PUNCT
eurjchem-1645	82	58	1h	1h	NUM
eurjchem-1645	82	59	,	,	PUNCT
eurjchem-1645	82	60	ar‐h	ar‐h	NOUN
eurjchem-1645	82	61	)	)	PUNCT
eurjchem-1645	82	62	.	.	PUNCT
eurjchem-1645	83	1	13c	13c	NOUN
eurjchem-1645	83	2	nmr	nmr	NOUN
eurjchem-1645	83	3	(	(	PUNCT
eurjchem-1645	83	4	100	100	NUM
eurjchem-1645	83	5	mhz	mhz	NOUN
eurjchem-1645	83	6	,	,	PUNCT
eurjchem-1645	83	7	cdcl3	cdcl3	PROPN
eurjchem-1645	83	8	,	,	PUNCT
eurjchem-1645	83	9	δ	δ	PROPN
eurjchem-1645	83	10	,	,	PUNCT
eurjchem-1645	83	11	ppm	ppm	NOUN
eurjchem-1645	83	12	):	):	PUNCT
eurjchem-1645	83	13	21.92	21.92	NUM
eurjchem-1645	83	14	,	,	PUNCT
eurjchem-1645	83	15	28.41	28.41	NUM
eurjchem-1645	83	16	,	,	PUNCT
eurjchem-1645	83	17	31.32	31.32	NUM
eurjchem-1645	83	18	,	,	PUNCT
eurjchem-1645	83	19	44.38	44.38	NUM
eurjchem-1645	83	20	,	,	PUNCT
eurjchem-1645	83	21	77.2	77.2	NUM
eurjchem-1645	83	22	,	,	PUNCT
eurjchem-1645	83	23	116.6	116.6	NUM
eurjchem-1645	83	24	,	,	PUNCT
eurjchem-1645	83	25	135.23	135.23	NUM
eurjchem-1645	83	26	,	,	PUNCT
eurjchem-1645	83	27	143.84	143.84	NUM
eurjchem-1645	83	28	,	,	PUNCT
eurjchem-1645	83	29	148.66	148.66	NUM
eurjchem-1645	83	30	.	.	PUNCT
eurjchem-1645	84	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	84	2	(	(	PUNCT
eurjchem-1645	84	3	ei	ei	PROPN
eurjchem-1645	84	4	,	,	PUNCT
eurjchem-1645	84	5	m	m	PROPN
eurjchem-1645	84	6	/	/	SYM
eurjchem-1645	84	7	z	z	NOUN
eurjchem-1645	84	8	):	):	PUNCT
eurjchem-1645	84	9	325	325	NUM
eurjchem-1645	84	10	(	(	PUNCT
eurjchem-1645	84	11	m+h	m+h	PROPN
eurjchem-1645	84	12	)	)	PUNCT
eurjchem-1645	84	13	.	.	PUNCT
eurjchem-1645	85	1	anal	anal	PROPN
eurjchem-1645	85	2	.	.	PUNCT
eurjchem-1645	85	3	calcd	calcd	NOUN
eurjchem-1645	85	4	.	.	PUNCT
eurjchem-1645	86	1	for	for	ADP
eurjchem-1645	86	2	c16h25n3o4	c16h25n3o4	NOUN
eurjchem-1645	86	3	:	:	PUNCT
eurjchem-1645	86	4	c	c	X
eurjchem-1645	86	5	,	,	PUNCT
eurjchem-1645	86	6	59.42	59.42	NUM
eurjchem-1645	86	7	;	;	PUNCT
eurjchem-1645	86	8	h	h	NOUN
eurjchem-1645	86	9	,	,	PUNCT
eurjchem-1645	86	10	7.79	7.79	NUM
eurjchem-1645	86	11	;	;	PUNCT
eurjchem-1645	86	12	n	n	CCONJ
eurjchem-1645	86	13	,	,	PUNCT
eurjchem-1645	86	14	12.99	12.99	NUM
eurjchem-1645	86	15	.	.	PUNCT
eurjchem-1645	86	16	found	find	VERB
eurjchem-1645	86	17	:	:	PUNCT
eurjchem-1645	87	1	c	c	X
eurjchem-1645	87	2	,	,	PUNCT
eurjchem-1645	87	3	59.40	59.40	NUM
eurjchem-1645	87	4	;	;	PUNCT
eurjchem-1645	87	5	h	h	NOUN
eurjchem-1645	87	6	,	,	PUNCT
eurjchem-1645	87	7	7.80	7.80	NUM
eurjchem-1645	87	8	;	;	PUNCT
eurjchem-1645	87	9	n	n	CCONJ
eurjchem-1645	87	10	,	,	PUNCT
eurjchem-1645	87	11	12.97	12.97	NUM
eurjchem-1645	87	12	%	%	NOUN
eurjchem-1645	87	13	.	.	PUNCT
eurjchem-1645	88	1	2.2.4	2.2.4	X
eurjchem-1645	88	2	.	.	X
eurjchem-1645	88	3	synthesis	synthesis	NOUN
eurjchem-1645	88	4	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	88	5	4,5,6,7‐tetrahydropyrazolo[3,4‐c	4,5,6,7‐tetrahydropyrazolo[3,4‐c	NOUN
eurjchem-1645	88	6	]	]	PUNCT
eurjchem-1645	88	7	pyridine‐1‐carboxylate	pyridine‐1‐carboxylate	ADJ
eurjchem-1645	88	8	(	(	PUNCT
eurjchem-1645	88	9	5	5	NUM
eurjchem-1645	88	10	)	)	PUNCT
eurjchem-1645	88	11	,	,	PUNCT
eurjchem-1645	88	12	step	step	NOUN
eurjchem-1645	88	13	(	(	PUNCT
eurjchem-1645	88	14	d	d	NOUN
eurjchem-1645	88	15	)	)	PUNCT
eurjchem-1645	88	16	to	to	ADP
eurjchem-1645	88	17	a	a	DET
eurjchem-1645	88	18	stirred	stir	VERB
eurjchem-1645	88	19	solution	solution	NOUN
eurjchem-1645	88	20	compound	compound	NOUN
eurjchem-1645	88	21	4	4	NUM
eurjchem-1645	88	22	(	(	PUNCT
eurjchem-1645	88	23	6.50	6.50	NUM
eurjchem-1645	88	24	g	g	NOUN
eurjchem-1645	88	25	,	,	PUNCT
eurjchem-1645	88	26	20.1	20.1	NUM
eurjchem-1645	88	27	mmol	mmol	NOUN
eurjchem-1645	88	28	)	)	PUNCT
eurjchem-1645	88	29	was	be	AUX
eurjchem-1645	88	30	dissolved	dissolve	VERB
eurjchem-1645	88	31	in	in	ADP
eurjchem-1645	88	32	2	2	NUM
eurjchem-1645	88	33	n	n	PRON
eurjchem-1645	88	34	hcl	hcl	PROPN
eurjchem-1645	88	35	(	(	PUNCT
eurjchem-1645	88	36	65	65	NUM
eurjchem-1645	88	37	ml	ml	NOUN
eurjchem-1645	88	38	)	)	PUNCT
eurjchem-1645	88	39	and	and	CCONJ
eurjchem-1645	88	40	stirred	stir	VERB
eurjchem-1645	88	41	reaction	reaction	NOUN
eurjchem-1645	88	42	mixture	mixture	NOUN
eurjchem-1645	88	43	to	to	PART
eurjchem-1645	88	44	room	room	VERB
eurjchem-1645	88	45	temperature	temperature	NOUN
eurjchem-1645	88	46	for	for	ADP
eurjchem-1645	88	47	2	2	NUM
eurjchem-1645	88	48	h.	h.	NOUN
eurjchem-1645	88	49	progress	progress	NOUN
eurjchem-1645	88	50	of	of	ADP
eurjchem-1645	88	51	reaction	reaction	NOUN
eurjchem-1645	88	52	was	be	AUX
eurjchem-1645	88	53	monitored	monitor	VERB
eurjchem-1645	88	54	by	by	ADP
eurjchem-1645	88	55	lc‐ms	lc‐ms	PRON
eurjchem-1645	88	56	for	for	ADP
eurjchem-1645	88	57	the	the	DET
eurjchem-1645	88	58	consumption	consumption	NOUN
eurjchem-1645	88	59	of	of	ADP
eurjchem-1645	88	60	starting	start	VERB
eurjchem-1645	88	61	material	material	NOUN
eurjchem-1645	88	62	.	.	PUNCT
eurjchem-1645	89	1	after	after	ADP
eurjchem-1645	89	2	completion	completion	NOUN
eurjchem-1645	89	3	the	the	DET
eurjchem-1645	89	4	reaction	reaction	NOUN
eurjchem-1645	89	5	,	,	PUNCT
eurjchem-1645	89	6	the	the	DET
eurjchem-1645	89	7	reaction	reaction	NOUN
eurjchem-1645	89	8	mixture	mixture	NOUN
eurjchem-1645	89	9	evaporated	evaporate	VERB
eurjchem-1645	89	10	under	under	ADP
eurjchem-1645	89	11	reduced	reduced	ADJ
eurjchem-1645	89	12	pressure	pressure	NOUN
eurjchem-1645	89	13	to	to	PART
eurjchem-1645	89	14	obtain	obtain	VERB
eurjchem-1645	89	15	yellow	yellow	ADJ
eurjchem-1645	89	16	gummy	gummy	ADJ
eurjchem-1645	89	17	material	material	NOUN
eurjchem-1645	89	18	.	.	PUNCT
eurjchem-1645	90	1	the	the	DET
eurjchem-1645	90	2	obtained	obtain	VERB
eurjchem-1645	90	3	crude	crude	NOUN
eurjchem-1645	90	4	was	be	AUX
eurjchem-1645	90	5	washed	wash	VERB
eurjchem-1645	90	6	with	with	ADP
eurjchem-1645	90	7	10	10	NUM
eurjchem-1645	90	8	%	%	NOUN
eurjchem-1645	90	9	ethyl	ethyl	PROPN
eurjchem-1645	90	10	acetate	acetate	NOUN
eurjchem-1645	90	11	:	:	PUNCT
eurjchem-1645	90	12	hexane	hexane	NOUN
eurjchem-1645	90	13	(	(	PUNCT
eurjchem-1645	90	14	v	v	NOUN
eurjchem-1645	90	15	:	:	PUNCT
eurjchem-1645	90	16	v,10:90	v,10:90	ADJ
eurjchem-1645	90	17	,	,	PUNCT
eurjchem-1645	90	18	25	25	NUM
eurjchem-1645	90	19	ml	ml	NOUN
eurjchem-1645	90	20	)	)	PUNCT
eurjchem-1645	90	21	,	,	PUNCT
eurjchem-1645	90	22	hexane	hexane	NOUN
eurjchem-1645	90	23	(	(	PUNCT
eurjchem-1645	90	24	50	50	NUM
eurjchem-1645	90	25	ml	ml	NOUN
eurjchem-1645	90	26	)	)	PUNCT
eurjchem-1645	90	27	and	and	CCONJ
eurjchem-1645	90	28	diethyl	diethyl	NOUN
eurjchem-1645	90	29	ether	ether	NOUN
eurjchem-1645	90	30	(	(	PUNCT
eurjchem-1645	90	31	50	50	NUM
eurjchem-1645	90	32	ml	ml	NOUN
eurjchem-1645	90	33	)	)	PUNCT
eurjchem-1645	90	34	to	to	PART
eurjchem-1645	90	35	obtain	obtain	VERB
eurjchem-1645	90	36	compound	compound	NOUN
eurjchem-1645	90	37	5	5	NUM
eurjchem-1645	90	38	.	.	PUNCT
eurjchem-1645	91	1	color	color	NOUN
eurjchem-1645	91	2	:	:	PUNCT
eurjchem-1645	91	3	yellow	yellow	ADJ
eurjchem-1645	91	4	.	.	PUNCT
eurjchem-1645	92	1	yield	yield	NOUN
eurjchem-1645	92	2	:	:	PUNCT
eurjchem-1645	92	3	89.3	89.3	NUM
eurjchem-1645	92	4	%	%	NOUN
eurjchem-1645	92	5	,	,	PUNCT
eurjchem-1645	92	6	4	4	NUM
eurjchem-1645	92	7	g.	g.	NOUN
eurjchem-1645	92	8	m.p	m.p	PROPN
eurjchem-1645	92	9	.	.	PROPN
eurjchem-1645	92	10	:	:	PUNCT
eurjchem-1645	92	11	61‐62	61‐62	NUM
eurjchem-1645	92	12	°	°	ADP
eurjchem-1645	92	13	c	c	NOUN
eurjchem-1645	92	14	.	.	PUNCT
eurjchem-1645	93	1	1h	1h	NUM
eurjchem-1645	93	2	nmr	nmr	NOUN
eurjchem-1645	93	3	(	(	PUNCT
eurjchem-1645	93	4	400	400	NUM
eurjchem-1645	93	5	mhz	mhz	NOUN
eurjchem-1645	93	6	,	,	PUNCT
eurjchem-1645	93	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	93	8	,	,	PUNCT
eurjchem-1645	93	9	δ	δ	PROPN
eurjchem-1645	93	10	,	,	PUNCT
eurjchem-1645	93	11	ppm	ppm	NUM
eurjchem-1645	93	12	):	):	PUNCT
eurjchem-1645	93	13	1.56	1.56	NUM
eurjchem-1645	93	14	(	(	PUNCT
eurjchem-1645	93	15	s	s	PROPN
eurjchem-1645	93	16	,	,	PUNCT
eurjchem-1645	93	17	9h	9h	NUM
eurjchem-1645	93	18	,	,	PUNCT
eurjchem-1645	93	19	n‐	n‐	NOUN
eurjchem-1645	93	20	t‐bu	t‐bu	NOUN
eurjchem-1645	93	21	)	)	PUNCT
eurjchem-1645	93	22	,	,	PUNCT
eurjchem-1645	93	23	2.21	2.21	NUM
eurjchem-1645	93	24	(	(	PUNCT
eurjchem-1645	93	25	d	d	PROPN
eurjchem-1645	93	26	,	,	PUNCT
eurjchem-1645	93	27	2h	2h	NUM
eurjchem-1645	93	28	,	,	PUNCT
eurjchem-1645	93	29	j	j	PROPN
eurjchem-1645	93	30	=	=	SYM
eurjchem-1645	93	31	6.2	6.2	NUM
eurjchem-1645	93	32	hz	hz	NOUN
eurjchem-1645	93	33	,	,	PUNCT
eurjchem-1645	93	34	ch2	ch2	PROPN
eurjchem-1645	93	35	)	)	PUNCT
eurjchem-1645	93	36	,	,	PUNCT
eurjchem-1645	93	37	2.78	2.78	NUM
eurjchem-1645	93	38	(	(	PUNCT
eurjchem-1645	93	39	m	m	PROPN
eurjchem-1645	93	40	,	,	PUNCT
eurjchem-1645	93	41	2h	2h	NUM
eurjchem-1645	93	42	,	,	PUNCT
eurjchem-1645	93	43	ch2	ch2	PROPN
eurjchem-1645	93	44	)	)	PUNCT
eurjchem-1645	93	45	,	,	PUNCT
eurjchem-1645	93	46	3.83	3.83	NUM
eurjchem-1645	93	47	(	(	PUNCT
eurjchem-1645	93	48	s	s	PROPN
eurjchem-1645	93	49	,	,	PUNCT
eurjchem-1645	93	50	2h	2h	NUM
eurjchem-1645	93	51	,	,	PUNCT
eurjchem-1645	93	52	n‐ch2	n‐ch2	PROPN
eurjchem-1645	93	53	)	)	PUNCT
eurjchem-1645	93	54	,	,	PUNCT
eurjchem-1645	93	55	7.31	7.31	NUM
eurjchem-1645	93	56	(	(	PUNCT
eurjchem-1645	93	57	s	s	PROPN
eurjchem-1645	93	58	,	,	PUNCT
eurjchem-1645	93	59	1h	1h	NUM
eurjchem-1645	93	60	,	,	PUNCT
eurjchem-1645	93	61	ar‐h	ar‐h	NOUN
eurjchem-1645	93	62	)	)	PUNCT
eurjchem-1645	93	63	.	.	PUNCT
eurjchem-1645	94	1	13c	13c	NOUN
eurjchem-1645	94	2	nmr	nmr	NOUN
eurjchem-1645	94	3	(	(	PUNCT
eurjchem-1645	94	4	100	100	NUM
eurjchem-1645	94	5	mhz	mhz	NOUN
eurjchem-1645	94	6	,	,	PUNCT
eurjchem-1645	94	7	cdcl3	cdcl3	PROPN
eurjchem-1645	94	8	,	,	PUNCT
eurjchem-1645	94	9	δ	δ	PROPN
eurjchem-1645	94	10	,	,	PUNCT
eurjchem-1645	94	11	ppm	ppm	NOUN
eurjchem-1645	94	12	):	):	PUNCT
eurjchem-1645	94	13	12.26	12.26	NUM
eurjchem-1645	94	14	,	,	PUNCT
eurjchem-1645	94	15	28.85	28.85	NUM
eurjchem-1645	94	16	,	,	PUNCT
eurjchem-1645	94	17	31.52	31.52	NUM
eurjchem-1645	94	18	,	,	PUNCT
eurjchem-1645	94	19	44.28	44.28	NUM
eurjchem-1645	94	20	,	,	PUNCT
eurjchem-1645	94	21	78.84	78.84	NUM
eurjchem-1645	94	22	,	,	PUNCT
eurjchem-1645	94	23	98.62	98.62	NUM
eurjchem-1645	94	24	,	,	PUNCT
eurjchem-1645	94	25	134.36	134.36	NUM
eurjchem-1645	94	26	,	,	PUNCT
eurjchem-1645	94	27	144.18	144.18	NUM
eurjchem-1645	94	28	,	,	PUNCT
eurjchem-1645	94	29	148.77	148.77	NUM
eurjchem-1645	94	30	.	.	PUNCT
eurjchem-1645	95	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	95	2	(	(	PUNCT
eurjchem-1645	95	3	ei	ei	PROPN
eurjchem-1645	95	4	,	,	PUNCT
eurjchem-1645	95	5	m	m	PROPN
eurjchem-1645	95	6	/	/	SYM
eurjchem-1645	95	7	z	z	NOUN
eurjchem-1645	95	8	):	):	PUNCT
eurjchem-1645	95	9	225	225	NUM
eurjchem-1645	95	10	(	(	PUNCT
eurjchem-1645	95	11	m+h	m+h	NOUN
eurjchem-1645	95	12	)	)	PUNCT
eurjchem-1645	95	13	.	.	PUNCT
eurjchem-1645	96	1	anal	anal	PROPN
eurjchem-1645	96	2	.	.	PUNCT
eurjchem-1645	96	3	calcd	calcd	NOUN
eurjchem-1645	96	4	.	.	PUNCT
eurjchem-1645	97	1	for	for	ADP
eurjchem-1645	97	2	c11h17n3o2	c11h17n3o2	PROPN
eurjchem-1645	97	3	:	:	PUNCT
eurjchem-1645	97	4	c	c	X
eurjchem-1645	97	5	,	,	PUNCT
eurjchem-1645	97	6	59.17	59.17	NUM
eurjchem-1645	97	7	;	;	PUNCT
eurjchem-1645	97	8	h	h	NOUN
eurjchem-1645	97	9	,	,	PUNCT
eurjchem-1645	97	10	7.67	7.67	NUM
eurjchem-1645	97	11	;	;	PUNCT
eurjchem-1645	97	12	n	n	CCONJ
eurjchem-1645	97	13	,	,	PUNCT
eurjchem-1645	97	14	18.82	18.82	NUM
eurjchem-1645	97	15	.	.	PUNCT
eurjchem-1645	97	16	found	find	VERB
eurjchem-1645	97	17	:	:	PUNCT
eurjchem-1645	98	1	c	c	X
eurjchem-1645	98	2	,	,	PUNCT
eurjchem-1645	98	3	59.19	59.19	NUM
eurjchem-1645	98	4	;	;	PUNCT
eurjchem-1645	98	5	h	h	NOUN
eurjchem-1645	98	6	,	,	PUNCT
eurjchem-1645	98	7	7.64	7.64	NUM
eurjchem-1645	98	8	;	;	PUNCT
eurjchem-1645	98	9	n	n	CCONJ
eurjchem-1645	98	10	,	,	PUNCT
eurjchem-1645	98	11	18.80	18.80	NUM
eurjchem-1645	98	12	%	%	NOUN
eurjchem-1645	98	13	.	.	PUNCT
eurjchem-1645	99	1	2.2.5	2.2.5	X
eurjchem-1645	99	2	.	.	X
eurjchem-1645	99	3	synthesis	synthesis	NOUN
eurjchem-1645	99	4	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	99	5	3‐bromo‐4,5,6,7‐tetrahydro	3‐bromo‐4,5,6,7‐tetrahydro	NUM
eurjchem-1645	99	6	pyrazolo[3,4‐c]pyridine‐1‐carboxylate	pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	99	7	(	(	PUNCT
eurjchem-1645	99	8	6	6	NUM
eurjchem-1645	99	9	)	)	PUNCT
eurjchem-1645	99	10	,	,	PUNCT
eurjchem-1645	99	11	step	step	NOUN
eurjchem-1645	99	12	(	(	PUNCT
eurjchem-1645	99	13	e	e	NOUN
eurjchem-1645	99	14	)	)	PUNCT
eurjchem-1645	99	15	to	to	ADP
eurjchem-1645	99	16	a	a	DET
eurjchem-1645	99	17	stirred	stir	VERB
eurjchem-1645	99	18	solution	solution	NOUN
eurjchem-1645	99	19	compound	compound	NOUN
eurjchem-1645	99	20	5	5	NUM
eurjchem-1645	99	21	(	(	PUNCT
eurjchem-1645	99	22	4.00	4.00	NUM
eurjchem-1645	99	23	g	g	NOUN
eurjchem-1645	99	24	,	,	PUNCT
eurjchem-1645	99	25	17.9	17.9	NUM
eurjchem-1645	99	26	mmol	mmol	NOUN
eurjchem-1645	99	27	)	)	PUNCT
eurjchem-1645	99	28	in	in	ADP
eurjchem-1645	99	29	thf	thf	NOUN
eurjchem-1645	99	30	(	(	PUNCT
eurjchem-1645	99	31	40	40	NUM
eurjchem-1645	99	32	ml	ml	NOUN
eurjchem-1645	99	33	)	)	PUNCT
eurjchem-1645	99	34	was	be	AUX
eurjchem-1645	99	35	added	add	VERB
eurjchem-1645	99	36	pyridine	pyridine	ADJ
eurjchem-1645	99	37	hydrobromide	hydrobromide	NOUN
eurjchem-1645	99	38	(	(	PUNCT
eurjchem-1645	99	39	5.74	5.74	NUM
eurjchem-1645	99	40	g	g	NOUN
eurjchem-1645	99	41	,	,	PUNCT
eurjchem-1645	99	42	35.8	35.8	NUM
eurjchem-1645	99	43	mmol	mmol	NOUN
eurjchem-1645	99	44	)	)	PUNCT
eurjchem-1645	99	45	drop	drop	NOUN
eurjchem-1645	99	46	wise	wise	ADJ
eurjchem-1645	99	47	at	at	ADP
eurjchem-1645	99	48	0	0	NUM
eurjchem-1645	99	49	°	°	NOUN
eurjchem-1645	99	50	c	c	NOUN
eurjchem-1645	99	51	.	.	PUNCT
eurjchem-1645	100	1	the	the	DET
eurjchem-1645	100	2	reaction	reaction	NOUN
eurjchem-1645	100	3	mixture	mixture	NOUN
eurjchem-1645	100	4	was	be	AUX
eurjchem-1645	100	5	stirred	stir	VERB
eurjchem-1645	100	6	at	at	ADP
eurjchem-1645	100	7	room	room	NOUN
eurjchem-1645	100	8	temperature	temperature	NOUN
eurjchem-1645	100	9	for	for	ADP
eurjchem-1645	100	10	3	3	NUM
eurjchem-1645	100	11	h.	h.	NOUN
eurjchem-1645	100	12	progress	progress	NOUN
eurjchem-1645	100	13	of	of	ADP
eurjchem-1645	100	14	reaction	reaction	NOUN
eurjchem-1645	100	15	was	be	AUX
eurjchem-1645	100	16	monitored	monitor	VERB
eurjchem-1645	100	17	by	by	ADP
eurjchem-1645	100	18	lc‐ms	lc‐ms	PRON
eurjchem-1645	100	19	for	for	ADP
eurjchem-1645	100	20	the	the	DET
eurjchem-1645	100	21	consumption	consumption	NOUN
eurjchem-1645	100	22	of	of	ADP
eurjchem-1645	100	23	starting	start	VERB
eurjchem-1645	100	24	material	material	NOUN
eurjchem-1645	100	25	.	.	PUNCT
eurjchem-1645	101	1	after	after	ADP
eurjchem-1645	101	2	comp‐	comp‐	VERB
eurjchem-1645	101	3	letion	letion	NOUN
eurjchem-1645	101	4	the	the	DET
eurjchem-1645	101	5	reaction	reaction	NOUN
eurjchem-1645	101	6	,	,	PUNCT
eurjchem-1645	101	7	the	the	DET
eurjchem-1645	101	8	reaction	reaction	NOUN
eurjchem-1645	101	9	mixture	mixture	NOUN
eurjchem-1645	101	10	evaporated	evaporate	VERB
eurjchem-1645	101	11	under	under	ADP
eurjchem-1645	101	12	reduced	reduced	ADJ
eurjchem-1645	101	13	pressure	pressure	NOUN
eurjchem-1645	101	14	to	to	PART
eurjchem-1645	101	15	obtain	obtain	VERB
eurjchem-1645	101	16	yellow	yellow	ADJ
eurjchem-1645	101	17	gummy	gummy	ADJ
eurjchem-1645	101	18	material	material	NOUN
eurjchem-1645	101	19	.	.	PUNCT
eurjchem-1645	102	1	the	the	DET
eurjchem-1645	102	2	obtained	obtain	VERB
eurjchem-1645	102	3	crude	crude	NOUN
eurjchem-1645	102	4	was	be	AUX
eurjchem-1645	102	5	washed	wash	VERB
eurjchem-1645	102	6	with	with	ADP
eurjchem-1645	102	7	10	10	NUM
eurjchem-1645	102	8	%	%	NOUN
eurjchem-1645	102	9	ethyl	ethyl	PROPN
eurjchem-1645	102	10	acetate	acetate	NOUN
eurjchem-1645	102	11	:	:	PUNCT
eurjchem-1645	102	12	hexane	hexane	NOUN
eurjchem-1645	102	13	(	(	PUNCT
eurjchem-1645	102	14	v	v	NOUN
eurjchem-1645	102	15	:	:	PUNCT
eurjchem-1645	102	16	v	v	NOUN
eurjchem-1645	102	17	,	,	PUNCT
eurjchem-1645	102	18	10	10	NUM
eurjchem-1645	102	19	:	:	SYM
eurjchem-1645	102	20	90	90	NUM
eurjchem-1645	102	21	,	,	PUNCT
eurjchem-1645	102	22	25	25	NUM
eurjchem-1645	102	23	ml	ml	NOUN
eurjchem-1645	102	24	)	)	PUNCT
eurjchem-1645	102	25	,	,	PUNCT
eurjchem-1645	102	26	hexane	hexane	NOUN
eurjchem-1645	102	27	(	(	PUNCT
eurjchem-1645	102	28	50	50	NUM
eurjchem-1645	102	29	ml	ml	NOUN
eurjchem-1645	102	30	)	)	PUNCT
eurjchem-1645	102	31	,	,	PUNCT
eurjchem-1645	102	32	and	and	CCONJ
eurjchem-1645	102	33	diethyl	diethyl	NOUN
eurjchem-1645	102	34	ether	ether	NOUN
eurjchem-1645	102	35	(	(	PUNCT
eurjchem-1645	102	36	50	50	NUM
eurjchem-1645	102	37	ml	ml	NOUN
eurjchem-1645	102	38	)	)	PUNCT
eurjchem-1645	102	39	,	,	PUNCT
eurjchem-1645	102	40	to	to	PART
eurjchem-1645	102	41	obtain	obtain	VERB
eurjchem-1645	102	42	compound	compound	NOUN
eurjchem-1645	102	43	6	6	NUM
eurjchem-1645	102	44	.	.	PUNCT
eurjchem-1645	103	1	color	color	NOUN
eurjchem-1645	103	2	:	:	PUNCT
eurjchem-1645	103	3	yellow	yellow	ADJ
eurjchem-1645	103	4	.	.	PUNCT
eurjchem-1645	104	1	yield	yield	NOUN
eurjchem-1645	104	2	:	:	PUNCT
eurjchem-1645	104	3	92	92	NUM
eurjchem-1645	104	4	%	%	NOUN
eurjchem-1645	104	5	,	,	PUNCT
eurjchem-1645	104	6	5	5	NUM
eurjchem-1645	104	7	g.	g.	PROPN
eurjchem-1645	104	8	m.p	m.p	PROPN
eurjchem-1645	104	9	.	.	PROPN
eurjchem-1645	104	10	:	:	PUNCT
eurjchem-1645	105	1	145‐146	145‐146	NUM
eurjchem-1645	105	2	°	°	PROPN
eurjchem-1645	105	3	c	c	PROPN
eurjchem-1645	105	4	.	.	PUNCT
eurjchem-1645	105	5	1h	1h	NUM
eurjchem-1645	105	6	nmr	nmr	NOUN
eurjchem-1645	105	7	(	(	PUNCT
eurjchem-1645	105	8	400	400	NUM
eurjchem-1645	105	9	mhz	mhz	NOUN
eurjchem-1645	105	10	,	,	PUNCT
eurjchem-1645	105	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	105	12	,	,	PUNCT
eurjchem-1645	105	13	δ	δ	PROPN
eurjchem-1645	105	14	,	,	PUNCT
eurjchem-1645	105	15	ppm	ppm	NOUN
eurjchem-1645	105	16	):	):	PUNCT
eurjchem-1645	105	17	1.39	1.39	NUM
eurjchem-1645	105	18	(	(	PUNCT
eurjchem-1645	105	19	s	s	PROPN
eurjchem-1645	105	20	,	,	PUNCT
eurjchem-1645	105	21	9h	9h	NOUN
eurjchem-1645	105	22	,	,	PUNCT
eurjchem-1645	105	23	n‐t‐bu	n‐t‐bu	PROPN
eurjchem-1645	105	24	)	)	PUNCT
eurjchem-1645	105	25	,	,	PUNCT
eurjchem-1645	105	26	2.49	2.49	NUM
eurjchem-1645	105	27	(	(	PUNCT
eurjchem-1645	105	28	d	d	NOUN
eurjchem-1645	105	29	,	,	PUNCT
eurjchem-1645	105	30	2h	2h	NUM
eurjchem-1645	105	31	,	,	PUNCT
eurjchem-1645	105	32	j	j	PROPN
eurjchem-1645	105	33	=	=	SYM
eurjchem-1645	105	34	6.2	6.2	NUM
eurjchem-1645	105	35	hz	hz	NOUN
eurjchem-1645	105	36	,	,	PUNCT
eurjchem-1645	105	37	ch2	ch2	PROPN
eurjchem-1645	105	38	)	)	PUNCT
eurjchem-1645	105	39	,	,	PUNCT
eurjchem-1645	105	40	2.88	2.88	NUM
eurjchem-1645	105	41	(	(	PUNCT
eurjchem-1645	105	42	m	m	PROPN
eurjchem-1645	105	43	,	,	PUNCT
eurjchem-1645	105	44	2h	2h	NUM
eurjchem-1645	105	45	,	,	PUNCT
eurjchem-1645	105	46	ch2	ch2	PROPN
eurjchem-1645	105	47	)	)	PUNCT
eurjchem-1645	105	48	,	,	PUNCT
eurjchem-1645	105	49	3.79	3.79	NUM
eurjchem-1645	105	50	(	(	PUNCT
eurjchem-1645	105	51	s	s	PROPN
eurjchem-1645	105	52	,	,	PUNCT
eurjchem-1645	105	53	2h	2h	NUM
eurjchem-1645	105	54	,	,	PUNCT
eurjchem-1645	105	55	n‐ch2	n‐ch2	PROPN
eurjchem-1645	105	56	)	)	PUNCT
eurjchem-1645	105	57	.	.	PUNCT
eurjchem-1645	106	1	13c	13c	NOUN
eurjchem-1645	106	2	nmr	nmr	NOUN
eurjchem-1645	106	3	(	(	PUNCT
eurjchem-1645	106	4	100	100	NUM
eurjchem-1645	106	5	mhz	mhz	NOUN
eurjchem-1645	106	6	,	,	PUNCT
eurjchem-1645	106	7	cdcl3	cdcl3	PROPN
eurjchem-1645	106	8	,	,	PUNCT
eurjchem-1645	106	9	δ	δ	PROPN
eurjchem-1645	106	10	,	,	PUNCT
eurjchem-1645	106	11	ppm	ppm	NOUN
eurjchem-1645	106	12	):	):	PUNCT
eurjchem-1645	106	13	14.33	14.33	NUM
eurjchem-1645	106	14	,	,	PUNCT
eurjchem-1645	106	15	28.41	28.41	NUM
eurjchem-1645	106	16	,	,	PUNCT
eurjchem-1645	106	17	30.76	30.76	NUM
eurjchem-1645	106	18	,	,	PUNCT
eurjchem-1645	106	19	4312	4312	NUM
eurjchem-1645	106	20	,	,	PUNCT
eurjchem-1645	106	21	78.81	78.81	NUM
eurjchem-1645	106	22	,	,	PUNCT
eurjchem-1645	106	23	115.61	115.61	NUM
eurjchem-1645	106	24	,	,	PUNCT
eurjchem-1645	106	25	123.10	123.10	NUM
eurjchem-1645	106	26	,	,	PUNCT
eurjchem-1645	106	27	139.18	139.18	NUM
eurjchem-1645	106	28	,	,	PUNCT
eurjchem-1645	106	29	148.88	148.88	NUM
eurjchem-1645	106	30	.	.	PUNCT
eurjchem-1645	107	1	lc‐	lc‐	ADJ
eurjchem-1645	107	2	ms	ms	PROPN
eurjchem-1645	107	3	(	(	PUNCT
eurjchem-1645	107	4	ei	ei	PROPN
eurjchem-1645	107	5	,	,	PUNCT
eurjchem-1645	107	6	m	m	PROPN
eurjchem-1645	107	7	/	/	SYM
eurjchem-1645	107	8	z	z	NOUN
eurjchem-1645	107	9	):	):	PUNCT
eurjchem-1645	107	10	303	303	NUM
eurjchem-1645	107	11	(	(	PUNCT
eurjchem-1645	107	12	m+h	m+h	NOUN
eurjchem-1645	107	13	)	)	PUNCT
eurjchem-1645	107	14	.	.	PUNCT
eurjchem-1645	108	1	anal	anal	PROPN
eurjchem-1645	108	2	.	.	PUNCT
eurjchem-1645	108	3	calcd	calcd	NOUN
eurjchem-1645	108	4	.	.	PUNCT
eurjchem-1645	109	1	for	for	ADP
eurjchem-1645	109	2	c11h16brn3o2	c11h16brn3o2	NOUN
eurjchem-1645	109	3	:	:	PUNCT
eurjchem-1645	109	4	c	c	X
eurjchem-1645	109	5	,	,	PUNCT
eurjchem-1645	109	6	47.72	47.72	NUM
eurjchem-1645	109	7	;	;	PUNCT
eurjchem-1645	109	8	h	h	NOUN
eurjchem-1645	109	9	,	,	PUNCT
eurjchem-1645	109	10	5.34	5.34	NUM
eurjchem-1645	109	11	;	;	PUNCT
eurjchem-1645	109	12	n	n	CCONJ
eurjchem-1645	109	13	,	,	PUNCT
eurjchem-1645	109	14	13.91	13.91	NUM
eurjchem-1645	109	15	.	.	PUNCT
eurjchem-1645	109	16	found	find	VERB
eurjchem-1645	109	17	:	:	PUNCT
eurjchem-1645	110	1	c	c	X
eurjchem-1645	110	2	,	,	PUNCT
eurjchem-1645	110	3	47.73	47.73	NUM
eurjchem-1645	110	4	;	;	PUNCT
eurjchem-1645	110	5	h	h	NOUN
eurjchem-1645	110	6	,	,	PUNCT
eurjchem-1645	110	7	5.32	5.32	NUM
eurjchem-1645	110	8	;	;	PUNCT
eurjchem-1645	110	9	n	n	CCONJ
eurjchem-1645	110	10	,	,	PUNCT
eurjchem-1645	110	11	13.90	13.90	NUM
eurjchem-1645	110	12	%	%	NOUN
eurjchem-1645	110	13	.	.	PUNCT
eurjchem-1645	111	1	2.2.6	2.2.6	X
eurjchem-1645	111	2	.	.	PUNCT
eurjchem-1645	112	1	synthesis	synthesis	NOUN
eurjchem-1645	112	2	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	112	3	4,5,6,7‐tetrahydro‐3‐hydroxy	4,5,6,7‐tetrahydro‐3‐hydroxy	NUM
eurjchem-1645	112	4	pyrazolo[3,4‐c]pyridine‐1‐carboxylate	pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	112	5	(	(	PUNCT
eurjchem-1645	112	6	7	7	NUM
eurjchem-1645	112	7	)	)	PUNCT
eurjchem-1645	112	8	,	,	PUNCT
eurjchem-1645	112	9	step	step	NOUN
eurjchem-1645	112	10	(	(	PUNCT
eurjchem-1645	112	11	f	f	X
eurjchem-1645	112	12	)	)	PUNCT
eurjchem-1645	112	13	to	to	ADP
eurjchem-1645	112	14	a	a	DET
eurjchem-1645	112	15	stirred	stir	VERB
eurjchem-1645	112	16	solution	solution	NOUN
eurjchem-1645	112	17	compound	compound	NOUN
eurjchem-1645	112	18	6	6	NUM
eurjchem-1645	112	19	(	(	PUNCT
eurjchem-1645	112	20	5.00	5.00	NUM
eurjchem-1645	112	21	g	g	NOUN
eurjchem-1645	112	22	,	,	PUNCT
eurjchem-1645	112	23	16.5	16.5	NUM
eurjchem-1645	112	24	mmol	mmol	NOUN
eurjchem-1645	112	25	)	)	PUNCT
eurjchem-1645	112	26	in	in	ADP
eurjchem-1645	112	27	2	2	NUM
eurjchem-1645	112	28	n	n	NOUN
eurjchem-1645	112	29	naoh	naoh	NOUN
eurjchem-1645	112	30	(	(	PUNCT
eurjchem-1645	112	31	50	50	NUM
eurjchem-1645	112	32	ml	ml	NOUN
eurjchem-1645	112	33	)	)	PUNCT
eurjchem-1645	112	34	and	and	CCONJ
eurjchem-1645	112	35	heat	heat	NOUN
eurjchem-1645	112	36	reaction	reaction	NOUN
eurjchem-1645	112	37	mixture	mixture	NOUN
eurjchem-1645	112	38	to	to	ADP
eurjchem-1645	112	39	100	100	NUM
eurjchem-1645	112	40	°	°	ADP
eurjchem-1645	112	41	c	c	NOUN
eurjchem-1645	112	42	for	for	ADP
eurjchem-1645	112	43	3	3	NUM
eurjchem-1645	112	44	h.	h.	NOUN
eurjchem-1645	112	45	progress	progress	NOUN
eurjchem-1645	112	46	of	of	ADP
eurjchem-1645	112	47	reaction	reaction	NOUN
eurjchem-1645	112	48	was	be	AUX
eurjchem-1645	112	49	monitored	monitor	VERB
eurjchem-1645	112	50	by	by	ADP
eurjchem-1645	112	51	lc‐ms	lc‐ms	PRON
eurjchem-1645	112	52	for	for	ADP
eurjchem-1645	112	53	the	the	DET
eurjchem-1645	112	54	con‐	con‐	NOUN
eurjchem-1645	112	55	sumption	sumption	NOUN
eurjchem-1645	112	56	of	of	ADP
eurjchem-1645	112	57	starting	start	VERB
eurjchem-1645	112	58	material	material	NOUN
eurjchem-1645	112	59	.	.	PUNCT
eurjchem-1645	113	1	after	after	ADP
eurjchem-1645	113	2	completion	completion	NOUN
eurjchem-1645	113	3	the	the	DET
eurjchem-1645	113	4	reaction	reaction	NOUN
eurjchem-1645	113	5	,	,	PUNCT
eurjchem-1645	113	6	the	the	DET
eurjchem-1645	113	7	reaction	reaction	NOUN
eurjchem-1645	113	8	mixture	mixture	NOUN
eurjchem-1645	113	9	evaporated	evaporate	VERB
eurjchem-1645	113	10	under	under	ADP
eurjchem-1645	113	11	reduced	reduced	ADJ
eurjchem-1645	113	12	pressure	pressure	NOUN
eurjchem-1645	113	13	to	to	PART
eurjchem-1645	113	14	obtain	obtain	VERB
eurjchem-1645	113	15	yellow	yellow	ADJ
eurjchem-1645	113	16	gummy	gummy	ADJ
eurjchem-1645	113	17	material	material	NOUN
eurjchem-1645	113	18	.	.	PUNCT
eurjchem-1645	114	1	the	the	DET
eurjchem-1645	114	2	obtained	obtain	VERB
eurjchem-1645	114	3	crude	crude	NOUN
eurjchem-1645	114	4	was	be	AUX
eurjchem-1645	114	5	washed	wash	VERB
eurjchem-1645	114	6	with	with	ADP
eurjchem-1645	114	7	10	10	NUM
eurjchem-1645	114	8	%	%	NOUN
eurjchem-1645	114	9	ethyl	ethyl	PROPN
eurjchem-1645	114	10	acetate	acetate	NOUN
eurjchem-1645	114	11	:	:	PUNCT
eurjchem-1645	114	12	hexane	hexane	NOUN
eurjchem-1645	114	13	(	(	PUNCT
eurjchem-1645	114	14	v	v	NOUN
eurjchem-1645	114	15	:	:	PUNCT
eurjchem-1645	114	16	v	v	NOUN
eurjchem-1645	114	17	,	,	PUNCT
eurjchem-1645	114	18	10:90	10:90	NUM
eurjchem-1645	114	19	,	,	PUNCT
eurjchem-1645	114	20	50	50	NUM
eurjchem-1645	114	21	ml	ml	NOUN
eurjchem-1645	114	22	)	)	PUNCT
eurjchem-1645	114	23	,	,	PUNCT
eurjchem-1645	114	24	hexane	hexane	NOUN
eurjchem-1645	114	25	(	(	PUNCT
eurjchem-1645	114	26	50	50	NUM
eurjchem-1645	114	27	ml	ml	NOUN
eurjchem-1645	114	28	)	)	PUNCT
eurjchem-1645	114	29	and	and	CCONJ
eurjchem-1645	114	30	diethyl	diethyl	NOUN
eurjchem-1645	114	31	ether	ether	NOUN
eurjchem-1645	114	32	(	(	PUNCT
eurjchem-1645	114	33	50	50	NUM
eurjchem-1645	114	34	ml	ml	NOUN
eurjchem-1645	114	35	)	)	PUNCT
eurjchem-1645	114	36	to	to	PART
eurjchem-1645	114	37	obtain	obtain	VERB
eurjchem-1645	114	38	compound	compound	NOUN
eurjchem-1645	114	39	7	7	NUM
eurjchem-1645	114	40	.	.	PUNCT
eurjchem-1645	115	1	color	color	NOUN
eurjchem-1645	115	2	:	:	PUNCT
eurjchem-1645	115	3	yellow	yellow	ADJ
eurjchem-1645	115	4	.	.	PUNCT
eurjchem-1645	116	1	yield	yield	NOUN
eurjchem-1645	116	2	:	:	PUNCT
eurjchem-1645	116	3	88.4	88.4	NUM
eurjchem-1645	116	4	%	%	NOUN
eurjchem-1645	116	5	,	,	PUNCT
eurjchem-1645	116	6	3.5	3.5	NUM
eurjchem-1645	116	7	g.	g.	NOUN
eurjchem-1645	116	8	m.p	m.p	PROPN
eurjchem-1645	116	9	.	.	PROPN
eurjchem-1645	116	10	:	:	PUNCT
eurjchem-1645	116	11	87‐88	87‐88	NUM
eurjchem-1645	116	12	°	°	ADP
eurjchem-1645	116	13	c	c	NOUN
eurjchem-1645	116	14	.	.	PUNCT
eurjchem-1645	117	1	1h	1h	NUM
eurjchem-1645	117	2	nmr	nmr	NOUN
eurjchem-1645	117	3	(	(	PUNCT
eurjchem-1645	117	4	400	400	NUM
eurjchem-1645	117	5	mhz	mhz	NOUN
eurjchem-1645	117	6	,	,	PUNCT
eurjchem-1645	117	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	117	8	,	,	PUNCT
eurjchem-1645	117	9	δ	δ	PROPN
eurjchem-1645	117	10	,	,	PUNCT
eurjchem-1645	117	11	ppm	ppm	NOUN
eurjchem-1645	117	12	):	):	PUNCT
eurjchem-1645	117	13	1.54	1.54	NUM
eurjchem-1645	117	14	(	(	PUNCT
eurjchem-1645	117	15	s	s	PROPN
eurjchem-1645	117	16	,	,	PUNCT
eurjchem-1645	117	17	9h	9h	NOUN
eurjchem-1645	117	18	,	,	PUNCT
eurjchem-1645	117	19	n‐t‐bu	n‐t‐bu	PROPN
eurjchem-1645	117	20	)	)	PUNCT
eurjchem-1645	117	21	,	,	PUNCT
eurjchem-1645	117	22	2.20	2.20	NUM
eurjchem-1645	117	23	(	(	PUNCT
eurjchem-1645	117	24	d	d	PROPN
eurjchem-1645	117	25	,	,	PUNCT
eurjchem-1645	117	26	2h	2h	NUM
eurjchem-1645	117	27	,	,	PUNCT
eurjchem-1645	117	28	j	j	PROPN
eurjchem-1645	117	29	=	=	SYM
eurjchem-1645	117	30	6.2	6.2	NUM
eurjchem-1645	117	31	hz	hz	NOUN
eurjchem-1645	117	32	,	,	PUNCT
eurjchem-1645	117	33	ch2	ch2	PROPN
eurjchem-1645	117	34	)	)	PUNCT
eurjchem-1645	117	35	,	,	PUNCT
eurjchem-1645	117	36	2.78	2.78	NUM
eurjchem-1645	117	37	(	(	PUNCT
eurjchem-1645	117	38	m	m	PROPN
eurjchem-1645	117	39	,	,	PUNCT
eurjchem-1645	117	40	2h	2h	NUM
eurjchem-1645	117	41	,	,	PUNCT
eurjchem-1645	117	42	ch2	ch2	PROPN
eurjchem-1645	117	43	)	)	PUNCT
eurjchem-1645	117	44	,	,	PUNCT
eurjchem-1645	117	45	3.79	3.79	NUM
eurjchem-1645	117	46	(	(	PUNCT
eurjchem-1645	117	47	s	s	PROPN
eurjchem-1645	117	48	,	,	PUNCT
eurjchem-1645	117	49	2h	2h	NUM
eurjchem-1645	117	50	,	,	PUNCT
eurjchem-1645	117	51	n‐ch2	n‐ch2	PROPN
eurjchem-1645	117	52	)	)	PUNCT
eurjchem-1645	117	53	.	.	PUNCT
eurjchem-1645	118	1	13c	13c	NOUN
eurjchem-1645	118	2	nmr	nmr	NOUN
eurjchem-1645	118	3	(	(	PUNCT
eurjchem-1645	118	4	100	100	NUM
eurjchem-1645	118	5	mhz	mhz	NOUN
eurjchem-1645	118	6	,	,	PUNCT
eurjchem-1645	118	7	cdcl3	cdcl3	PROPN
eurjchem-1645	118	8	,	,	PUNCT
eurjchem-1645	118	9	δ	δ	PROPN
eurjchem-1645	118	10	,	,	PUNCT
eurjchem-1645	118	11	ppm	ppm	NUM
eurjchem-1645	118	12	):	):	PUNCT
eurjchem-1645	118	13	12.23	12.23	NUM
eurjchem-1645	118	14	,	,	PUNCT
eurjchem-1645	118	15	28.41	28.41	NUM
eurjchem-1645	118	16	,	,	PUNCT
eurjchem-1645	118	17	31.76	31.76	NUM
eurjchem-1645	118	18	,	,	PUNCT
eurjchem-1645	118	19	44.36	44.36	NUM
eurjchem-1645	118	20	,	,	PUNCT
eurjchem-1645	118	21	78.88	78.88	NUM
eurjchem-1645	118	22	,	,	PUNCT
eurjchem-1645	118	23	99.10	99.10	NUM
eurjchem-1645	118	24	,	,	PUNCT
eurjchem-1645	118	25	134.17	134.17	NUM
eurjchem-1645	118	26	,	,	PUNCT
eurjchem-1645	118	27	144.16	144.16	NUM
eurjchem-1645	118	28	,	,	PUNCT
eurjchem-1645	118	29	147.46	147.46	NUM
eurjchem-1645	118	30	.	.	PUNCT
eurjchem-1645	119	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	119	2	(	(	PUNCT
eurjchem-1645	119	3	ei	ei	PROPN
eurjchem-1645	119	4	,	,	PUNCT
eurjchem-1645	119	5	m	m	PROPN
eurjchem-1645	119	6	/	/	SYM
eurjchem-1645	119	7	z	z	NOUN
eurjchem-1645	119	8	):	):	PUNCT
eurjchem-1645	119	9	240	240	NUM
eurjchem-1645	119	10	(	(	PUNCT
eurjchem-1645	119	11	m+h	m+h	NOUN
eurjchem-1645	119	12	)	)	PUNCT
eurjchem-1645	119	13	.	.	PUNCT
eurjchem-1645	120	1	anal	anal	PROPN
eurjchem-1645	120	2	.	.	PUNCT
eurjchem-1645	120	3	calcd	calcd	NOUN
eurjchem-1645	120	4	.	.	PUNCT
eurjchem-1645	121	1	for	for	ADP
eurjchem-1645	121	2	c11h17n3o3	c11h17n3o3	PROPN
eurjchem-1645	121	3	:	:	PUNCT
eurjchem-1645	121	4	c	c	X
eurjchem-1645	121	5	,	,	PUNCT
eurjchem-1645	121	6	55.22	55.22	NUM
eurjchem-1645	121	7	;	;	PUNCT
eurjchem-1645	121	8	h	h	X
eurjchem-1645	121	9	,	,	PUNCT
eurjchem-1645	121	10	7.16	7.16	NUM
eurjchem-1645	121	11	;	;	PUNCT
eurjchem-1645	121	12	n	n	CCONJ
eurjchem-1645	121	13	,	,	PUNCT
eurjchem-1645	121	14	17.56	17.56	NUM
eurjchem-1645	121	15	.	.	PUNCT
eurjchem-1645	122	1	found	find	VERB
eurjchem-1645	122	2	:	:	PUNCT
eurjchem-1645	123	1	c	c	X
eurjchem-1645	123	2	,	,	PUNCT
eurjchem-1645	123	3	55.20	55.20	NUM
eurjchem-1645	123	4	;	;	PUNCT
eurjchem-1645	123	5	h	h	X
eurjchem-1645	123	6	,	,	PUNCT
eurjchem-1645	123	7	7.18	7.18	NUM
eurjchem-1645	123	8	;	;	PUNCT
eurjchem-1645	123	9	n	n	CCONJ
eurjchem-1645	123	10	,	,	PUNCT
eurjchem-1645	123	11	17.58	17.58	NUM
eurjchem-1645	123	12	%	%	NOUN
eurjchem-1645	123	13	.	.	PUNCT
eurjchem-1645	124	1	2.2.7	2.2.7	X
eurjchem-1645	124	2	.	.	PUNCT
eurjchem-1645	125	1	synthesis	synthesis	NOUN
eurjchem-1645	125	2	of	of	ADP
eurjchem-1645	125	3	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	125	4	6‐benzyl‐4,5,6,7‐tetrahydro‐3‐	6‐benzyl‐4,5,6,7‐tetrahydro‐3‐	NUM
eurjchem-1645	125	5	hydroxypyrazolo[3,4‐c]pyridine‐1‐carboxylate	hydroxypyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	125	6	(	(	PUNCT
eurjchem-1645	125	7	8)	8)	NUM
eurjchem-1645	125	8	,	,	PUNCT
eurjchem-1645	125	9	step	step	NOUN
eurjchem-1645	125	10	(	(	PUNCT
eurjchem-1645	125	11	g	g	NOUN
eurjchem-1645	125	12	)	)	PUNCT
eurjchem-1645	125	13	to	to	ADP
eurjchem-1645	125	14	a	a	DET
eurjchem-1645	125	15	stirred	stir	VERB
eurjchem-1645	125	16	solution	solution	NOUN
eurjchem-1645	125	17	of	of	ADP
eurjchem-1645	125	18	compound	compound	NOUN
eurjchem-1645	125	19	7	7	NUM
eurjchem-1645	125	20	(	(	PUNCT
eurjchem-1645	125	21	3.50	3.50	NUM
eurjchem-1645	125	22	g	g	NOUN
eurjchem-1645	125	23	,	,	PUNCT
eurjchem-1645	125	24	14.6	14.6	NUM
eurjchem-1645	125	25	mmol	mmol	NOUN
eurjchem-1645	125	26	)	)	PUNCT
eurjchem-1645	125	27	in	in	ADP
eurjchem-1645	125	28	thf	thf	NOUN
eurjchem-1645	125	29	(	(	PUNCT
eurjchem-1645	125	30	35	35	NUM
eurjchem-1645	125	31	ml	ml	NOUN
eurjchem-1645	125	32	)	)	PUNCT
eurjchem-1645	125	33	was	be	AUX
eurjchem-1645	125	34	added	add	VERB
eurjchem-1645	125	35	2,6‐lutidine	2,6‐lutidine	NUM
eurjchem-1645	125	36	(	(	PUNCT
eurjchem-1645	125	37	3.14	3.14	NUM
eurjchem-1645	125	38	g	g	NOUN
eurjchem-1645	125	39	,	,	PUNCT
eurjchem-1645	125	40	29.3	29.3	NUM
eurjchem-1645	125	41	mmol	mmol	NOUN
eurjchem-1645	125	42	)	)	PUNCT
eurjchem-1645	125	43	,	,	PUNCT
eurjchem-1645	125	44	dmap	dmap	NOUN
eurjchem-1645	125	45	(	(	PUNCT
eurjchem-1645	125	46	0.36	0.36	NUM
eurjchem-1645	125	47	g	g	NOUN
eurjchem-1645	125	48	,	,	PUNCT
eurjchem-1645	125	49	2.93	2.93	NUM
eurjchem-1645	125	50	mmol	mmol	NOUN
eurjchem-1645	125	51	)	)	PUNCT
eurjchem-1645	125	52	and	and	CCONJ
eurjchem-1645	125	53	benzyl	benzyl	NOUN
eurjchem-1645	125	54	bromide	bromide	NOUN
eurjchem-1645	125	55	(	(	PUNCT
eurjchem-1645	125	56	2.98	2.98	NUM
eurjchem-1645	125	57	g	g	NOUN
eurjchem-1645	125	58	,	,	PUNCT
eurjchem-1645	125	59	16.1	16.1	NUM
eurjchem-1645	125	60	mmol	mmol	NOUN
eurjchem-1645	125	61	)	)	PUNCT
eurjchem-1645	125	62	.	.	PUNCT
eurjchem-1645	126	1	the	the	DET
eurjchem-1645	126	2	reaction	reaction	NOUN
eurjchem-1645	126	3	mixture	mixture	NOUN
eurjchem-1645	126	4	was	be	AUX
eurjchem-1645	126	5	stirred	stir	VERB
eurjchem-1645	126	6	at	at	ADP
eurjchem-1645	126	7	room	room	NOUN
eurjchem-1645	126	8	temperature	temperature	NOUN
eurjchem-1645	126	9	for	for	ADP
eurjchem-1645	126	10	6	6	NUM
eurjchem-1645	126	11	h.	h.	NOUN
eurjchem-1645	126	12	progress	progress	NOUN
eurjchem-1645	126	13	of	of	ADP
eurjchem-1645	126	14	reaction	reaction	NOUN
eurjchem-1645	126	15	was	be	AUX
eurjchem-1645	126	16	monitored	monitor	VERB
eurjchem-1645	126	17	by	by	ADP
eurjchem-1645	126	18	lc‐ms	lc‐ms	PRON
eurjchem-1645	126	19	for	for	ADP
eurjchem-1645	126	20	the	the	DET
eurjchem-1645	126	21	consumption	consumption	NOUN
eurjchem-1645	126	22	of	of	ADP
eurjchem-1645	126	23	starting	start	VERB
eurjchem-1645	126	24	material	material	NOUN
eurjchem-1645	126	25	.	.	PUNCT
eurjchem-1645	127	1	after	after	ADP
eurjchem-1645	127	2	completion	completion	NOUN
eurjchem-1645	127	3	the	the	DET
eurjchem-1645	127	4	reaction	reaction	NOUN
eurjchem-1645	127	5	,	,	PUNCT
eurjchem-1645	127	6	the	the	DET
eurjchem-1645	127	7	reaction	reaction	NOUN
eurjchem-1645	127	8	mixture	mixture	NOUN
eurjchem-1645	127	9	evaporated	evaporate	VERB
eurjchem-1645	127	10	under	under	ADP
eurjchem-1645	127	11	reduced	reduced	ADJ
eurjchem-1645	127	12	pressure	pressure	NOUN
eurjchem-1645	127	13	to	to	PART
eurjchem-1645	127	14	obtain	obtain	VERB
eurjchem-1645	127	15	yellow	yellow	ADJ
eurjchem-1645	127	16	gummy	gummy	ADJ
eurjchem-1645	127	17	material	material	NOUN
eurjchem-1645	127	18	.	.	PUNCT
eurjchem-1645	128	1	the	the	DET
eurjchem-1645	128	2	obtained	obtain	VERB
eurjchem-1645	128	3	crude	crude	NOUN
eurjchem-1645	128	4	was	be	AUX
eurjchem-1645	128	5	washed	wash	VERB
eurjchem-1645	128	6	with	with	ADP
eurjchem-1645	128	7	10	10	NUM
eurjchem-1645	128	8	%	%	NOUN
eurjchem-1645	128	9	ethyl	ethyl	PROPN
eurjchem-1645	128	10	acetate	acetate	NOUN
eurjchem-1645	128	11	:	:	PUNCT
eurjchem-1645	128	12	hexane	hexane	NOUN
eurjchem-1645	128	13	(	(	PUNCT
eurjchem-1645	128	14	v	v	NOUN
eurjchem-1645	128	15	:	:	PUNCT
eurjchem-1645	128	16	v	v	NOUN
eurjchem-1645	128	17	,	,	PUNCT
eurjchem-1645	128	18	10:90	10:90	NUM
eurjchem-1645	128	19	,	,	PUNCT
eurjchem-1645	128	20	50	50	NUM
eurjchem-1645	128	21	ml	ml	NOUN
eurjchem-1645	128	22	)	)	PUNCT
eurjchem-1645	128	23	,	,	PUNCT
eurjchem-1645	128	24	hexane	hexane	NOUN
eurjchem-1645	128	25	(	(	PUNCT
eurjchem-1645	128	26	50	50	NUM
eurjchem-1645	128	27	ml	ml	NOUN
eurjchem-1645	128	28	)	)	PUNCT
eurjchem-1645	128	29	,	,	PUNCT
eurjchem-1645	128	30	and	and	CCONJ
eurjchem-1645	128	31	diethyl	diethyl	NOUN
eurjchem-1645	128	32	ether	ether	NOUN
eurjchem-1645	128	33	(	(	PUNCT
eurjchem-1645	128	34	50	50	NUM
eurjchem-1645	128	35	ml	ml	NOUN
eurjchem-1645	128	36	)	)	PUNCT
eurjchem-1645	128	37	,	,	PUNCT
eurjchem-1645	128	38	to	to	PART
eurjchem-1645	128	39	obtain	obtain	VERB
eurjchem-1645	128	40	compound	compound	NOUN
eurjchem-1645	128	41	8	8	NUM
eurjchem-1645	128	42	.	.	PUNCT
eurjchem-1645	129	1	color	color	NOUN
eurjchem-1645	129	2	:	:	PUNCT
eurjchem-1645	129	3	yellow	yellow	ADJ
eurjchem-1645	129	4	.	.	PUNCT
eurjchem-1645	130	1	yield	yield	NOUN
eurjchem-1645	130	2	:	:	PUNCT
eurjchem-1645	130	3	83	83	NUM
eurjchem-1645	130	4	%	%	NOUN
eurjchem-1645	130	5	,	,	PUNCT
eurjchem-1645	130	6	4.5	4.5	NUM
eurjchem-1645	130	7	g.	g.	PROPN
eurjchem-1645	130	8	m.p	m.p	PROPN
eurjchem-1645	130	9	.	.	PROPN
eurjchem-1645	130	10	:	:	PUNCT
eurjchem-1645	131	1	133‐134	133‐134	NUM
eurjchem-1645	131	2	°	°	SYM
eurjchem-1645	131	3	c	c	PROPN
eurjchem-1645	131	4	.	.	PUNCT
eurjchem-1645	131	5	1h	1h	NUM
eurjchem-1645	131	6	nmr	nmr	NOUN
eurjchem-1645	131	7	(	(	PUNCT
eurjchem-1645	131	8	400	400	NUM
eurjchem-1645	131	9	mhz	mhz	NOUN
eurjchem-1645	131	10	,	,	PUNCT
eurjchem-1645	131	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	131	12	,	,	PUNCT
eurjchem-1645	131	13	δ	δ	PROPN
eurjchem-1645	131	14	,	,	PUNCT
eurjchem-1645	131	15	ppm	ppm	NOUN
eurjchem-1645	131	16	):	):	PUNCT
eurjchem-1645	131	17	1.42	1.42	NUM
eurjchem-1645	131	18	(	(	PUNCT
eurjchem-1645	131	19	s	s	PROPN
eurjchem-1645	131	20	,	,	PUNCT
eurjchem-1645	131	21	9h	9h	NUM
eurjchem-1645	131	22	,	,	PUNCT
eurjchem-1645	131	23	t‐bu	t‐bu	NOUN
eurjchem-1645	131	24	)	)	PUNCT
eurjchem-1645	131	25	,	,	PUNCT
eurjchem-1645	131	26	2.34	2.34	NUM
eurjchem-1645	131	27	(	(	PUNCT
eurjchem-1645	131	28	d	d	PROPN
eurjchem-1645	131	29	,	,	PUNCT
eurjchem-1645	131	30	2h	2h	NUM
eurjchem-1645	131	31	,	,	PUNCT
eurjchem-1645	131	32	j	j	PROPN
eurjchem-1645	131	33	=	=	PROPN
eurjchem-1645	131	34	6.4	6.4	NUM
eurjchem-1645	131	35	hz	hz	NOUN
eurjchem-1645	131	36	,	,	PUNCT
eurjchem-1645	131	37	ch2	ch2	PROPN
eurjchem-1645	131	38	)	)	PUNCT
eurjchem-1645	131	39	,	,	PUNCT
eurjchem-1645	131	40	2.68	2.68	NUM
eurjchem-1645	131	41	(	(	PUNCT
eurjchem-1645	131	42	m	m	PROPN
eurjchem-1645	131	43	,	,	PUNCT
eurjchem-1645	131	44	2h	2h	NUM
eurjchem-1645	131	45	,	,	PUNCT
eurjchem-1645	131	46	ch2	ch2	PROPN
eurjchem-1645	131	47	)	)	PUNCT
eurjchem-1645	131	48	,	,	PUNCT
eurjchem-1645	131	49	3.60	3.60	NUM
eurjchem-1645	131	50	(	(	PUNCT
eurjchem-1645	131	51	s	s	PROPN
eurjchem-1645	131	52	,	,	PUNCT
eurjchem-1645	131	53	2h	2h	NUM
eurjchem-1645	131	54	,	,	PUNCT
eurjchem-1645	131	55	ch2	ch2	PROPN
eurjchem-1645	131	56	)	)	PUNCT
eurjchem-1645	131	57	,	,	PUNCT
eurjchem-1645	131	58	3.70	3.70	NUM
eurjchem-1645	131	59	(	(	PUNCT
eurjchem-1645	131	60	s	s	PROPN
eurjchem-1645	131	61	,	,	PUNCT
eurjchem-1645	131	62	2h	2h	NUM
eurjchem-1645	131	63	,	,	PUNCT
eurjchem-1645	131	64	n‐ch2	n‐ch2	PROPN
eurjchem-1645	131	65	)	)	PUNCT
eurjchem-1645	131	66	,	,	PUNCT
eurjchem-1645	132	1	7.38‐7.28	7.38‐7.28	NUM
eurjchem-1645	132	2	(	(	PUNCT
eurjchem-1645	132	3	m	m	PROPN
eurjchem-1645	132	4	,	,	PUNCT
eurjchem-1645	132	5	5h	5h	NUM
eurjchem-1645	132	6	,	,	PUNCT
eurjchem-1645	132	7	ar‐h	ar‐h	NOUN
eurjchem-1645	132	8	)	)	PUNCT
eurjchem-1645	132	9	.	.	PUNCT
eurjchem-1645	133	1	13c	13c	NOUN
eurjchem-1645	133	2	nmr	nmr	NOUN
eurjchem-1645	133	3	(	(	PUNCT
eurjchem-1645	133	4	100	100	NUM
eurjchem-1645	133	5	mhz	mhz	NOUN
eurjchem-1645	133	6	,	,	PUNCT
eurjchem-1645	133	7	cdcl3	cdcl3	PROPN
eurjchem-1645	133	8	,	,	PUNCT
eurjchem-1645	133	9	δ	δ	PROPN
eurjchem-1645	133	10	,	,	PUNCT
eurjchem-1645	133	11	ppm	ppm	NOUN
eurjchem-1645	133	12	):	):	PUNCT
eurjchem-1645	133	13	9.88	9.88	NUM
eurjchem-1645	133	14	,	,	PUNCT
eurjchem-1645	133	15	28.41	28.41	NUM
eurjchem-1645	133	16	,	,	PUNCT
eurjchem-1645	133	17	43.44	43.44	NUM
eurjchem-1645	133	18	,	,	PUNCT
eurjchem-1645	133	19	52.12	52.12	NUM
eurjchem-1645	133	20	,	,	PUNCT
eurjchem-1645	133	21	60.18	60.18	NUM
eurjchem-1645	133	22	,	,	PUNCT
eurjchem-1645	133	23	pawar	pawar	PROPN
eurjchem-1645	133	24	et	et	PROPN
eurjchem-1645	133	25	al	al	PROPN
eurjchem-1645	133	26	.	.	PUNCT
eurjchem-1645	133	27	/	/	SYM
eurjchem-1645	133	28	european	european	PROPN
eurjchem-1645	133	29	journal	journal	PROPN
eurjchem-1645	133	30	of	of	ADP
eurjchem-1645	133	31	chemistry	chemistry	NOUN
eurjchem-1645	133	32	8	8	NUM
eurjchem-1645	133	33	(	(	PUNCT
eurjchem-1645	133	34	4	4	NUM
eurjchem-1645	133	35	)	)	PUNCT
eurjchem-1645	133	36	(	(	PUNCT
eurjchem-1645	133	37	2017	2017	NUM
eurjchem-1645	133	38	)	)	PUNCT
eurjchem-1645	133	39	400‐409	400‐409	NUM
eurjchem-1645	133	40	403	403	NUM
eurjchem-1645	133	41	78.81	78.81	NUM
eurjchem-1645	133	42	,	,	PUNCT
eurjchem-1645	133	43	98.67	98.67	NUM
eurjchem-1645	133	44	,	,	PUNCT
eurjchem-1645	133	45	127.62	127.62	NUM
eurjchem-1645	133	46	,	,	PUNCT
eurjchem-1645	133	47	128.21	128.21	NUM
eurjchem-1645	133	48	,	,	PUNCT
eurjchem-1645	133	49	128.34	128.34	NUM
eurjchem-1645	133	50	,	,	PUNCT
eurjchem-1645	133	51	128.46	128.46	NUM
eurjchem-1645	133	52	,	,	PUNCT
eurjchem-1645	133	53	128.58	128.58	NUM
eurjchem-1645	133	54	,	,	PUNCT
eurjchem-1645	133	55	135.11	135.11	NUM
eurjchem-1645	133	56	,	,	PUNCT
eurjchem-1645	133	57	135.21	135.21	NUM
eurjchem-1645	133	58	,	,	PUNCT
eurjchem-1645	133	59	144.66	144.66	NUM
eurjchem-1645	133	60	,	,	PUNCT
eurjchem-1645	133	61	148.78	148.78	NUM
eurjchem-1645	133	62	.	.	PUNCT
eurjchem-1645	134	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	134	2	(	(	PUNCT
eurjchem-1645	134	3	ei	ei	PROPN
eurjchem-1645	134	4	,	,	PUNCT
eurjchem-1645	134	5	m	m	PROPN
eurjchem-1645	134	6	/	/	SYM
eurjchem-1645	134	7	z	z	NOUN
eurjchem-1645	134	8	):	):	PUNCT
eurjchem-1645	134	9	330	330	NUM
eurjchem-1645	134	10	(	(	PUNCT
eurjchem-1645	134	11	m+h	m+h	NOUN
eurjchem-1645	134	12	)	)	PUNCT
eurjchem-1645	134	13	.	.	PUNCT
eurjchem-1645	135	1	anal	anal	PROPN
eurjchem-1645	135	2	.	.	PUNCT
eurjchem-1645	135	3	calcd	calcd	NOUN
eurjchem-1645	135	4	.	.	PUNCT
eurjchem-1645	136	1	for	for	ADP
eurjchem-1645	136	2	c18h23n3o3	c18h23n3o3	PROPN
eurjchem-1645	136	3	:	:	PUNCT
eurjchem-1645	136	4	c	c	X
eurjchem-1645	136	5	,	,	PUNCT
eurjchem-1645	136	6	65.63	65.63	NUM
eurjchem-1645	136	7	;	;	PUNCT
eurjchem-1645	136	8	h	h	NOUN
eurjchem-1645	136	9	,	,	PUNCT
eurjchem-1645	136	10	7.04	7.04	NUM
eurjchem-1645	136	11	;	;	PUNCT
eurjchem-1645	136	12	n	n	CCONJ
eurjchem-1645	136	13	,	,	PUNCT
eurjchem-1645	136	14	12.76	12.76	NUM
eurjchem-1645	136	15	.	.	PUNCT
eurjchem-1645	136	16	found	find	VERB
eurjchem-1645	136	17	:	:	PUNCT
eurjchem-1645	137	1	c	c	X
eurjchem-1645	137	2	,	,	PUNCT
eurjchem-1645	137	3	65.65	65.65	NUM
eurjchem-1645	137	4	;	;	PUNCT
eurjchem-1645	137	5	h	h	NOUN
eurjchem-1645	137	6	,	,	PUNCT
eurjchem-1645	137	7	7.01	7.01	NUM
eurjchem-1645	137	8	;	;	PUNCT
eurjchem-1645	137	9	n	n	CCONJ
eurjchem-1645	137	10	,	,	PUNCT
eurjchem-1645	137	11	12.78	12.78	NUM
eurjchem-1645	137	12	%	%	NOUN
eurjchem-1645	137	13	.	.	PUNCT
eurjchem-1645	138	1	2.2.8	2.2.8	X
eurjchem-1645	138	2	.	.	PUNCT
eurjchem-1645	139	1	synthesis	synthesis	NOUN
eurjchem-1645	139	2	of	of	ADP
eurjchem-1645	139	3	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	139	4	3‐(2,2,2‐trifluoroacetoyloxy)‐6‐	3‐(2,2,2‐trifluoroacetoyloxy)‐6‐	NUM
eurjchem-1645	139	5	benzyl‐4,5,6,7‐tetrahydropyrazolo[3,4‐c]pyridine‐1‐	benzyl‐4,5,6,7‐tetrahydropyrazolo[3,4‐c]pyridine‐1‐	ADJ
eurjchem-1645	139	6	carboxylate	carboxylate	NOUN
eurjchem-1645	139	7	(	(	PUNCT
eurjchem-1645	139	8	9	9	NUM
eurjchem-1645	139	9	)	)	PUNCT
eurjchem-1645	139	10	,	,	PUNCT
eurjchem-1645	139	11	step	step	NOUN
eurjchem-1645	139	12	(	(	PUNCT
eurjchem-1645	139	13	h	h	NOUN
eurjchem-1645	139	14	)	)	PUNCT
eurjchem-1645	139	15	to	to	ADP
eurjchem-1645	139	16	a	a	DET
eurjchem-1645	139	17	stirred	stir	VERB
eurjchem-1645	139	18	solution	solution	NOUN
eurjchem-1645	139	19	of	of	ADP
eurjchem-1645	139	20	synthesis	synthesis	NOUN
eurjchem-1645	139	21	of	of	ADP
eurjchem-1645	139	22	compound	compound	NOUN
eurjchem-1645	139	23	8	8	NUM
eurjchem-1645	139	24	(	(	PUNCT
eurjchem-1645	139	25	3.50	3.50	NUM
eurjchem-1645	139	26	g	g	NOUN
eurjchem-1645	139	27	,	,	PUNCT
eurjchem-1645	139	28	10.6	10.6	NUM
eurjchem-1645	139	29	mmol	mmol	NOUN
eurjchem-1645	139	30	)	)	PUNCT
eurjchem-1645	139	31	in	in	ADP
eurjchem-1645	139	32	dcm	dcm	PROPN
eurjchem-1645	139	33	(	(	PUNCT
eurjchem-1645	139	34	35	35	NUM
eurjchem-1645	139	35	ml	ml	NOUN
eurjchem-1645	139	36	)	)	PUNCT
eurjchem-1645	139	37	,	,	PUNCT
eurjchem-1645	139	38	triethylamine	triethylamine	NOUN
eurjchem-1645	139	39	(	(	PUNCT
eurjchem-1645	139	40	2.12	2.12	NUM
eurjchem-1645	139	41	ml	ml	NOUN
eurjchem-1645	139	42	,	,	PUNCT
eurjchem-1645	139	43	15.9	15.9	NUM
eurjchem-1645	139	44	mmol	mmol	NOUN
eurjchem-1645	139	45	)	)	PUNCT
eurjchem-1645	139	46	was	be	AUX
eurjchem-1645	139	47	added	add	VERB
eurjchem-1645	139	48	triflouromethanesulfonicanhydride	triflouromethanesulfonicanhydride	ADJ
eurjchem-1645	139	49	(	(	PUNCT
eurjchem-1645	139	50	3.60	3.60	NUM
eurjchem-1645	139	51	g	g	NOUN
eurjchem-1645	139	52	,	,	PUNCT
eurjchem-1645	139	53	12.8	12.8	NUM
eurjchem-1645	139	54	mmol	mmol	NOUN
eurjchem-1645	139	55	)	)	PUNCT
eurjchem-1645	139	56	drop	drop	NOUN
eurjchem-1645	139	57	wise	wise	ADJ
eurjchem-1645	139	58	at	at	ADP
eurjchem-1645	139	59	0	0	NUM
eurjchem-1645	139	60	°	°	NOUN
eurjchem-1645	139	61	c	c	NOUN
eurjchem-1645	139	62	.	.	PUNCT
eurjchem-1645	140	1	the	the	DET
eurjchem-1645	140	2	reaction	reaction	NOUN
eurjchem-1645	140	3	mixture	mixture	NOUN
eurjchem-1645	140	4	was	be	AUX
eurjchem-1645	140	5	stirred	stir	VERB
eurjchem-1645	140	6	at	at	ADP
eurjchem-1645	140	7	room	room	NOUN
eurjchem-1645	140	8	temperature	temperature	NOUN
eurjchem-1645	140	9	for	for	ADP
eurjchem-1645	140	10	12	12	NUM
eurjchem-1645	140	11	h.	h.	NOUN
eurjchem-1645	140	12	progress	progress	NOUN
eurjchem-1645	140	13	of	of	ADP
eurjchem-1645	140	14	reaction	reaction	NOUN
eurjchem-1645	140	15	was	be	AUX
eurjchem-1645	140	16	monitored	monitor	VERB
eurjchem-1645	140	17	by	by	ADP
eurjchem-1645	140	18	lc‐ms	lc‐ms	PRON
eurjchem-1645	140	19	for	for	ADP
eurjchem-1645	140	20	the	the	DET
eurjchem-1645	140	21	consumption	consumption	NOUN
eurjchem-1645	140	22	of	of	ADP
eurjchem-1645	140	23	starting	start	VERB
eurjchem-1645	140	24	material	material	NOUN
eurjchem-1645	140	25	.	.	PUNCT
eurjchem-1645	141	1	after	after	ADP
eurjchem-1645	141	2	completion	completion	NOUN
eurjchem-1645	141	3	the	the	DET
eurjchem-1645	141	4	reaction	reaction	NOUN
eurjchem-1645	141	5	,	,	PUNCT
eurjchem-1645	141	6	the	the	DET
eurjchem-1645	141	7	reaction	reaction	NOUN
eurjchem-1645	141	8	mixture	mixture	NOUN
eurjchem-1645	141	9	evaporated	evaporate	VERB
eurjchem-1645	141	10	under	under	ADP
eurjchem-1645	141	11	reduced	reduced	ADJ
eurjchem-1645	141	12	pressure	pressure	NOUN
eurjchem-1645	141	13	to	to	PART
eurjchem-1645	141	14	obtain	obtain	VERB
eurjchem-1645	141	15	yellow	yellow	ADJ
eurjchem-1645	141	16	gummy	gummy	ADJ
eurjchem-1645	141	17	material	material	NOUN
eurjchem-1645	141	18	.	.	PUNCT
eurjchem-1645	142	1	the	the	DET
eurjchem-1645	142	2	obtained	obtain	VERB
eurjchem-1645	142	3	crude	crude	NOUN
eurjchem-1645	142	4	was	be	AUX
eurjchem-1645	142	5	washed	wash	VERB
eurjchem-1645	142	6	with	with	ADP
eurjchem-1645	142	7	10	10	NUM
eurjchem-1645	142	8	%	%	NOUN
eurjchem-1645	142	9	ethyl	ethyl	PROPN
eurjchem-1645	142	10	acetate	acetate	NOUN
eurjchem-1645	142	11	:	:	PUNCT
eurjchem-1645	142	12	hexane	hexane	NOUN
eurjchem-1645	142	13	(	(	PUNCT
eurjchem-1645	142	14	v	v	NOUN
eurjchem-1645	142	15	:	:	PUNCT
eurjchem-1645	142	16	v	v	NOUN
eurjchem-1645	142	17	,	,	PUNCT
eurjchem-1645	142	18	10:90	10:90	NUM
eurjchem-1645	142	19	,	,	PUNCT
eurjchem-1645	142	20	50	50	NUM
eurjchem-1645	142	21	ml	ml	NOUN
eurjchem-1645	142	22	)	)	PUNCT
eurjchem-1645	142	23	,	,	PUNCT
eurjchem-1645	142	24	hexane	hexane	NOUN
eurjchem-1645	142	25	(	(	PUNCT
eurjchem-1645	142	26	50	50	NUM
eurjchem-1645	142	27	ml	ml	NOUN
eurjchem-1645	142	28	)	)	PUNCT
eurjchem-1645	142	29	,	,	PUNCT
eurjchem-1645	142	30	and	and	CCONJ
eurjchem-1645	142	31	diethyl	diethyl	NOUN
eurjchem-1645	142	32	ether	ether	NOUN
eurjchem-1645	142	33	(	(	PUNCT
eurjchem-1645	142	34	50	50	NUM
eurjchem-1645	142	35	ml	ml	NOUN
eurjchem-1645	142	36	)	)	PUNCT
eurjchem-1645	142	37	,	,	PUNCT
eurjchem-1645	142	38	to	to	PART
eurjchem-1645	142	39	obtain	obtain	VERB
eurjchem-1645	142	40	compound	compound	NOUN
eurjchem-1645	142	41	9	9	NUM
eurjchem-1645	142	42	.	.	PUNCT
eurjchem-1645	143	1	color	color	NOUN
eurjchem-1645	143	2	:	:	PUNCT
eurjchem-1645	143	3	yellow	yellow	ADJ
eurjchem-1645	143	4	.	.	PUNCT
eurjchem-1645	144	1	yield	yield	NOUN
eurjchem-1645	144	2	:	:	PUNCT
eurjchem-1645	144	3	88.5	88.5	NUM
eurjchem-1645	144	4	%	%	NOUN
eurjchem-1645	144	5	,	,	PUNCT
eurjchem-1645	144	6	4	4	NUM
eurjchem-1645	144	7	g.	g.	NOUN
eurjchem-1645	144	8	m.p	m.p	PROPN
eurjchem-1645	144	9	.	.	PROPN
eurjchem-1645	144	10	:	:	PUNCT
eurjchem-1645	145	1	173‐174	173‐174	PROPN
eurjchem-1645	145	2	°	°	PROPN
eurjchem-1645	145	3	c	c	PROPN
eurjchem-1645	145	4	.	.	PUNCT
eurjchem-1645	146	1	1h	1h	NUM
eurjchem-1645	146	2	nmr	nmr	NOUN
eurjchem-1645	146	3	(	(	PUNCT
eurjchem-1645	146	4	400	400	NUM
eurjchem-1645	146	5	mhz	mhz	NOUN
eurjchem-1645	146	6	,	,	PUNCT
eurjchem-1645	146	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	146	8	,	,	PUNCT
eurjchem-1645	146	9	δ	δ	PROPN
eurjchem-1645	146	10	,	,	PUNCT
eurjchem-1645	146	11	ppm	ppm	NOUN
eurjchem-1645	146	12	):	):	PUNCT
eurjchem-1645	146	13	1.40	1.40	NUM
eurjchem-1645	146	14	(	(	PUNCT
eurjchem-1645	146	15	s	s	PROPN
eurjchem-1645	146	16	,	,	PUNCT
eurjchem-1645	146	17	9h	9h	NUM
eurjchem-1645	146	18	,	,	PUNCT
eurjchem-1645	146	19	t‐bu	t‐bu	NOUN
eurjchem-1645	146	20	)	)	PUNCT
eurjchem-1645	146	21	,	,	PUNCT
eurjchem-1645	146	22	2.34	2.34	NUM
eurjchem-1645	146	23	(	(	PUNCT
eurjchem-1645	146	24	d	d	PROPN
eurjchem-1645	146	25	,	,	PUNCT
eurjchem-1645	146	26	2h	2h	NUM
eurjchem-1645	146	27	,	,	PUNCT
eurjchem-1645	146	28	j	j	PROPN
eurjchem-1645	146	29	=	=	PROPN
eurjchem-1645	146	30	6.4	6.4	NUM
eurjchem-1645	146	31	hz	hz	NOUN
eurjchem-1645	146	32	,	,	PUNCT
eurjchem-1645	146	33	ch2	ch2	PROPN
eurjchem-1645	146	34	)	)	PUNCT
eurjchem-1645	146	35	,	,	PUNCT
eurjchem-1645	146	36	2.68	2.68	NUM
eurjchem-1645	146	37	(	(	PUNCT
eurjchem-1645	146	38	m	m	PROPN
eurjchem-1645	146	39	,	,	PUNCT
eurjchem-1645	146	40	2h	2h	NUM
eurjchem-1645	146	41	,	,	PUNCT
eurjchem-1645	146	42	ch2	ch2	PROPN
eurjchem-1645	146	43	)	)	PUNCT
eurjchem-1645	146	44	,	,	PUNCT
eurjchem-1645	146	45	3.60	3.60	NUM
eurjchem-1645	146	46	(	(	PUNCT
eurjchem-1645	146	47	s	s	PROPN
eurjchem-1645	146	48	,	,	PUNCT
eurjchem-1645	146	49	2h	2h	NUM
eurjchem-1645	146	50	,	,	PUNCT
eurjchem-1645	146	51	ch2	ch2	PROPN
eurjchem-1645	146	52	)	)	PUNCT
eurjchem-1645	146	53	,	,	PUNCT
eurjchem-1645	146	54	3.70	3.70	NUM
eurjchem-1645	146	55	(	(	PUNCT
eurjchem-1645	146	56	s	s	PROPN
eurjchem-1645	146	57	,	,	PUNCT
eurjchem-1645	146	58	2h	2h	NUM
eurjchem-1645	146	59	,	,	PUNCT
eurjchem-1645	146	60	n‐ch2	n‐ch2	PROPN
eurjchem-1645	146	61	)	)	PUNCT
eurjchem-1645	146	62	,	,	PUNCT
eurjchem-1645	147	1	7.38‐7.28	7.38‐7.28	NUM
eurjchem-1645	147	2	(	(	PUNCT
eurjchem-1645	147	3	m	m	PROPN
eurjchem-1645	147	4	,	,	PUNCT
eurjchem-1645	147	5	5h	5h	NUM
eurjchem-1645	147	6	,	,	PUNCT
eurjchem-1645	147	7	ar‐h	ar‐h	NOUN
eurjchem-1645	147	8	)	)	PUNCT
eurjchem-1645	147	9	.	.	PUNCT
eurjchem-1645	148	1	13c	13c	NOUN
eurjchem-1645	148	2	nmr	nmr	NOUN
eurjchem-1645	148	3	(	(	PUNCT
eurjchem-1645	148	4	100	100	NUM
eurjchem-1645	148	5	mhz	mhz	NOUN
eurjchem-1645	148	6	,	,	PUNCT
eurjchem-1645	148	7	cdcl3	cdcl3	PROPN
eurjchem-1645	148	8	,	,	PUNCT
eurjchem-1645	148	9	δ	δ	PROPN
eurjchem-1645	148	10	,	,	PUNCT
eurjchem-1645	148	11	ppm	ppm	NOUN
eurjchem-1645	148	12	):	):	PUNCT
eurjchem-1645	148	13	9.86	9.86	NUM
eurjchem-1645	148	14	,	,	PUNCT
eurjchem-1645	148	15	28.41	28.41	NUM
eurjchem-1645	148	16	,	,	PUNCT
eurjchem-1645	148	17	43.44	43.44	NUM
eurjchem-1645	148	18	,	,	PUNCT
eurjchem-1645	148	19	52.12	52.12	NUM
eurjchem-1645	148	20	,	,	PUNCT
eurjchem-1645	148	21	60.18	60.18	NUM
eurjchem-1645	148	22	,	,	PUNCT
eurjchem-1645	148	23	78.80	78.80	NUM
eurjchem-1645	148	24	,	,	PUNCT
eurjchem-1645	148	25	98.68	98.68	NUM
eurjchem-1645	148	26	,	,	PUNCT
eurjchem-1645	148	27	112.13	112.13	NUM
eurjchem-1645	148	28	,	,	PUNCT
eurjchem-1645	148	29	127.72	127.72	NUM
eurjchem-1645	148	30	,	,	PUNCT
eurjchem-1645	148	31	128.22	128.22	NUM
eurjchem-1645	148	32	,	,	PUNCT
eurjchem-1645	148	33	128.32	128.32	NUM
eurjchem-1645	148	34	,	,	PUNCT
eurjchem-1645	148	35	128.46	128.46	NUM
eurjchem-1645	148	36	,	,	PUNCT
eurjchem-1645	148	37	128.58	128.58	NUM
eurjchem-1645	148	38	,	,	PUNCT
eurjchem-1645	148	39	135.13	135.13	NUM
eurjchem-1645	148	40	,	,	PUNCT
eurjchem-1645	148	41	135.22	135.22	NUM
eurjchem-1645	148	42	,	,	PUNCT
eurjchem-1645	148	43	144.66	144.66	NUM
eurjchem-1645	148	44	,	,	PUNCT
eurjchem-1645	148	45	148.78	148.78	NUM
eurjchem-1645	148	46	,	,	PUNCT
eurjchem-1645	148	47	168.34	168.34	NUM
eurjchem-1645	148	48	.	.	PUNCT
eurjchem-1645	149	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	149	2	(	(	PUNCT
eurjchem-1645	149	3	ei	ei	X
eurjchem-1645	149	4	,	,	PUNCT
eurjchem-1645	149	5	m	m	PROPN
eurjchem-1645	149	6	/	/	SYM
eurjchem-1645	149	7	z	z	NOUN
eurjchem-1645	149	8	):	):	PUNCT
eurjchem-1645	149	9	426	426	NUM
eurjchem-1645	149	10	(	(	PUNCT
eurjchem-1645	149	11	m+h	m+h	PROPN
eurjchem-1645	149	12	)	)	PUNCT
eurjchem-1645	149	13	.	.	PUNCT
eurjchem-1645	150	1	anal	anal	PROPN
eurjchem-1645	150	2	.	.	PUNCT
eurjchem-1645	150	3	calcd	calcd	NOUN
eurjchem-1645	150	4	.	.	PUNCT
eurjchem-1645	151	1	for	for	ADP
eurjchem-1645	151	2	c20h22f3n3o4	c20h22f3n3o4	NOUN
eurjchem-1645	151	3	:	:	PUNCT
eurjchem-1645	151	4	c	c	X
eurjchem-1645	151	5	,	,	PUNCT
eurjchem-1645	151	6	56.47	56.47	NUM
eurjchem-1645	151	7	;	;	PUNCT
eurjchem-1645	151	8	h	h	NOUN
eurjchem-1645	151	9	,	,	PUNCT
eurjchem-1645	151	10	5.21	5.21	NUM
eurjchem-1645	151	11	;	;	PUNCT
eurjchem-1645	151	12	n	n	CCONJ
eurjchem-1645	151	13	,	,	PUNCT
eurjchem-1645	151	14	9.88	9.88	NUM
eurjchem-1645	151	15	.	.	PUNCT
eurjchem-1645	151	16	found	find	VERB
eurjchem-1645	151	17	:	:	PUNCT
eurjchem-1645	152	1	c	c	X
eurjchem-1645	152	2	,	,	PUNCT
eurjchem-1645	152	3	56.44	56.44	NUM
eurjchem-1645	152	4	;	;	PUNCT
eurjchem-1645	152	5	h	h	X
eurjchem-1645	152	6	,	,	PUNCT
eurjchem-1645	152	7	5.20	5.20	NUM
eurjchem-1645	152	8	;	;	PUNCT
eurjchem-1645	152	9	n	n	CCONJ
eurjchem-1645	152	10	,	,	PUNCT
eurjchem-1645	152	11	9.90	9.90	NUM
eurjchem-1645	152	12	%	%	NOUN
eurjchem-1645	152	13	.	.	PUNCT
eurjchem-1645	153	1	2.2.9	2.2.9	X
eurjchem-1645	153	2	.	.	PUNCT
eurjchem-1645	153	3	general	general	ADJ
eurjchem-1645	153	4	procedure	procedure	NOUN
eurjchem-1645	153	5	for	for	ADP
eurjchem-1645	153	6	synthesis	synthesis	NOUN
eurjchem-1645	153	7	of	of	ADP
eurjchem-1645	153	8	compounds	compound	NOUN
eurjchem-1645	153	9	10a‐d	10a‐d	NOUN
eurjchem-1645	153	10	,	,	PUNCT
eurjchem-1645	153	11	step	step	NOUN
eurjchem-1645	153	12	(	(	PUNCT
eurjchem-1645	153	13	i	i	NOUN
eurjchem-1645	153	14	)	)	PUNCT
eurjchem-1645	153	15	to	to	ADP
eurjchem-1645	153	16	a	a	DET
eurjchem-1645	153	17	stirred	stir	VERB
eurjchem-1645	153	18	solution	solution	NOUN
eurjchem-1645	153	19	of	of	ADP
eurjchem-1645	153	20	compound	compound	NOUN
eurjchem-1645	153	21	9	9	NUM
eurjchem-1645	153	22	(	(	PUNCT
eurjchem-1645	153	23	1	1	NUM
eurjchem-1645	153	24	mmol	mmol	NOUN
eurjchem-1645	153	25	)	)	PUNCT
eurjchem-1645	153	26	in	in	ADP
eurjchem-1645	153	27	toluene	toluene	NOUN
eurjchem-1645	153	28	(	(	PUNCT
eurjchem-1645	153	29	5	5	NUM
eurjchem-1645	153	30	ml	ml	NOUN
eurjchem-1645	153	31	)	)	PUNCT
eurjchem-1645	153	32	was	be	AUX
eurjchem-1645	153	33	substituted	substitute	VERB
eurjchem-1645	153	34	aromatic	aromatic	ADJ
eurjchem-1645	153	35	boronic	boronic	ADJ
eurjchem-1645	153	36	acid	acid	NOUN
eurjchem-1645	153	37	(	(	PUNCT
eurjchem-1645	153	38	2	2	NUM
eurjchem-1645	153	39	mmol	mmol	NOUN
eurjchem-1645	153	40	)	)	PUNCT
eurjchem-1645	153	41	,	,	PUNCT
eurjchem-1645	153	42	2‐	2‐	NUM
eurjchem-1645	153	43	dicyclohexylphosphino‐2,6‐diisopropoxybiphenyl	dicyclohexylphosphino‐2,6‐diisopropoxybiphenyl	NOUN
eurjchem-1645	153	44	(	(	PUNCT
eurjchem-1645	153	45	0.2	0.2	NUM
eurjchem-1645	153	46	mmol	mmol	NOUN
eurjchem-1645	153	47	)	)	PUNCT
eurjchem-1645	153	48	,	,	PUNCT
eurjchem-1645	153	49	cesium	cesium	NOUN
eurjchem-1645	153	50	carbonate	carbonate	NOUN
eurjchem-1645	153	51	(	(	PUNCT
eurjchem-1645	153	52	3	3	NUM
eurjchem-1645	153	53	mmol	mmol	NOUN
eurjchem-1645	153	54	)	)	PUNCT
eurjchem-1645	153	55	and	and	CCONJ
eurjchem-1645	153	56	tris(dibenzylideneacetone	tris(dibenzylideneacetone	NOUN
eurjchem-1645	153	57	)	)	PUNCT
eurjchem-1645	153	58	dipalladium(0	dipalladium(0	NOUN
eurjchem-1645	153	59	)	)	PUNCT
eurjchem-1645	153	60	(	(	PUNCT
eurjchem-1645	153	61	0.2	0.2	NUM
eurjchem-1645	153	62	mmol	mmol	NOUN
eurjchem-1645	153	63	)	)	PUNCT
eurjchem-1645	153	64	.	.	PUNCT
eurjchem-1645	154	1	the	the	DET
eurjchem-1645	154	2	reaction	reaction	NOUN
eurjchem-1645	154	3	mixture	mixture	NOUN
eurjchem-1645	154	4	was	be	AUX
eurjchem-1645	154	5	purged	purge	VERB
eurjchem-1645	154	6	with	with	ADP
eurjchem-1645	154	7	argon	argon	NOUN
eurjchem-1645	154	8	for	for	ADP
eurjchem-1645	154	9	10	10	NUM
eurjchem-1645	154	10	min	min	NOUN
eurjchem-1645	154	11	and	and	CCONJ
eurjchem-1645	154	12	heat	heat	NOUN
eurjchem-1645	154	13	reaction	reaction	NOUN
eurjchem-1645	154	14	mixture	mixture	NOUN
eurjchem-1645	154	15	to	to	ADP
eurjchem-1645	154	16	100	100	NUM
eurjchem-1645	154	17	°	°	ADP
eurjchem-1645	154	18	c	c	NOUN
eurjchem-1645	154	19	for	for	ADP
eurjchem-1645	154	20	6	6	NUM
eurjchem-1645	154	21	h.	h.	NOUN
eurjchem-1645	154	22	progress	progress	NOUN
eurjchem-1645	154	23	of	of	ADP
eurjchem-1645	154	24	reaction	reaction	NOUN
eurjchem-1645	154	25	was	be	AUX
eurjchem-1645	154	26	monitored	monitor	VERB
eurjchem-1645	154	27	by	by	ADP
eurjchem-1645	154	28	lc‐ms	lc‐ms	X
eurjchem-1645	154	29	.	.	PUNCT
eurjchem-1645	155	1	after	after	ADP
eurjchem-1645	155	2	completion	completion	NOUN
eurjchem-1645	155	3	the	the	DET
eurjchem-1645	155	4	reaction	reaction	NOUN
eurjchem-1645	155	5	,	,	PUNCT
eurjchem-1645	155	6	the	the	DET
eurjchem-1645	155	7	reaction	reaction	NOUN
eurjchem-1645	155	8	mixture	mixture	NOUN
eurjchem-1645	155	9	was	be	AUX
eurjchem-1645	155	10	filtered	filter	VERB
eurjchem-1645	155	11	through	through	ADP
eurjchem-1645	155	12	a	a	DET
eurjchem-1645	155	13	pad	pad	NOUN
eurjchem-1645	155	14	of	of	ADP
eurjchem-1645	155	15	celite	celite	ADJ
eurjchem-1645	155	16	,	,	PUNCT
eurjchem-1645	155	17	washed	wash	VERB
eurjchem-1645	155	18	with	with	ADP
eurjchem-1645	155	19	etoac	etoac	ADJ
eurjchem-1645	155	20	(	(	PUNCT
eurjchem-1645	155	21	10	10	NUM
eurjchem-1645	155	22	ml	ml	NOUN
eurjchem-1645	155	23	)	)	PUNCT
eurjchem-1645	155	24	and	and	CCONJ
eurjchem-1645	155	25	saturated	saturate	VERB
eurjchem-1645	155	26	cold	cold	ADJ
eurjchem-1645	155	27	sodium	sodium	NOUN
eurjchem-1645	155	28	chloride	chloride	NOUN
eurjchem-1645	155	29	solution	solution	NOUN
eurjchem-1645	155	30	(	(	PUNCT
eurjchem-1645	155	31	2×5	2×5	NUM
eurjchem-1645	155	32	ml	ml	NOUN
eurjchem-1645	155	33	)	)	PUNCT
eurjchem-1645	155	34	and	and	CCONJ
eurjchem-1645	155	35	organic	organic	ADJ
eurjchem-1645	155	36	layer	layer	NOUN
eurjchem-1645	155	37	was	be	AUX
eurjchem-1645	155	38	evaporated	evaporate	VERB
eurjchem-1645	155	39	under	under	ADP
eurjchem-1645	155	40	reduced	reduce	VERB
eurjchem-1645	155	41	pressure	pressure	NOUN
eurjchem-1645	155	42	to	to	PART
eurjchem-1645	155	43	obtain	obtain	VERB
eurjchem-1645	155	44	crude	crude	ADJ
eurjchem-1645	155	45	gummy	gummy	ADJ
eurjchem-1645	155	46	material	material	NOUN
eurjchem-1645	155	47	(	(	PUNCT
eurjchem-1645	155	48	10a‐d	10a‐d	NOUN
eurjchem-1645	155	49	)	)	PUNCT
eurjchem-1645	155	50	.	.	PUNCT
eurjchem-1645	156	1	the	the	DET
eurjchem-1645	156	2	obtained	obtain	VERB
eurjchem-1645	156	3	crude	crude	NOUN
eurjchem-1645	156	4	was	be	AUX
eurjchem-1645	156	5	purified	purify	VERB
eurjchem-1645	156	6	by	by	ADP
eurjchem-1645	156	7	silica	silica	NOUN
eurjchem-1645	156	8	gel	gel	NOUN
eurjchem-1645	156	9	(	(	PUNCT
eurjchem-1645	156	10	230‐400	230‐400	PROPN
eurjchem-1645	156	11	mesh	mesh	NOUN
eurjchem-1645	156	12	)	)	PUNCT
eurjchem-1645	156	13	by	by	ADP
eurjchem-1645	156	14	using	use	VERB
eurjchem-1645	156	15	ethyl	ethyl	PROPN
eurjchem-1645	156	16	acetate	acetate	NOUN
eurjchem-1645	156	17	:	:	PUNCT
eurjchem-1645	156	18	heptane	heptane	NOUN
eurjchem-1645	156	19	(	(	PUNCT
eurjchem-1645	156	20	15:85	15:85	NUM
eurjchem-1645	156	21	,	,	PUNCT
eurjchem-1645	156	22	v	v	NOUN
eurjchem-1645	156	23	:	:	SYM
eurjchem-1645	156	24	v	v	NOUN
eurjchem-1645	156	25	)	)	PUNCT
eurjchem-1645	156	26	to	to	PART
eurjchem-1645	156	27	obtain	obtain	VERB
eurjchem-1645	156	28	compound	compound	NOUN
eurjchem-1645	156	29	10a‐d	10a‐d	NOUN
eurjchem-1645	156	30	.	.	PUNCT
eurjchem-1645	157	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	157	2	3‐(benzofuran‐2‐yl)‐6‐benzyl‐4	3‐(benzofuran‐2‐yl)‐6‐benzyl‐4	NOUN
eurjchem-1645	157	3	,	,	PUNCT
eurjchem-1645	157	4	5	5	NUM
eurjchem-1645	157	5	,	,	PUNCT
eurjchem-1645	157	6	6	6	NUM
eurjchem-1645	157	7	,	,	PUNCT
eurjchem-1645	157	8	7‐tetrahydro	7‐tetrahydro	NUM
eurjchem-1645	157	9	pyrazolo[3,4‐c]pyridine‐1‐carboxylate	pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	157	10	(	(	PUNCT
eurjchem-1645	157	11	10a	10a	NUM
eurjchem-1645	157	12	):	):	PUNCT
eurjchem-1645	158	1	color	color	NOUN
eurjchem-1645	158	2	:	:	PUNCT
eurjchem-1645	158	3	brown	brown	ADJ
eurjchem-1645	158	4	.	.	PUNCT
eurjchem-1645	158	5	yield	yield	NOUN
eurjchem-1645	158	6	:	:	PUNCT
eurjchem-1645	158	7	83	83	NUM
eurjchem-1645	158	8	%	%	NOUN
eurjchem-1645	158	9	.	.	PUNCT
eurjchem-1645	159	1	m.p	m.p	PROPN
eurjchem-1645	159	2	.	.	PROPN
eurjchem-1645	159	3	:	:	PUNCT
eurjchem-1645	160	1	131‐132	131‐132	X
eurjchem-1645	160	2	°	°	SYM
eurjchem-1645	160	3	c	c	NOUN
eurjchem-1645	160	4	.	.	PUNCT
eurjchem-1645	161	1	1h	1h	NUM
eurjchem-1645	161	2	nmr	nmr	NOUN
eurjchem-1645	161	3	(	(	PUNCT
eurjchem-1645	161	4	400	400	NUM
eurjchem-1645	161	5	mhz	mhz	NOUN
eurjchem-1645	161	6	,	,	PUNCT
eurjchem-1645	161	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	161	8	,	,	PUNCT
eurjchem-1645	161	9	δ	δ	PROPN
eurjchem-1645	161	10	,	,	PUNCT
eurjchem-1645	161	11	ppm	ppm	NUM
eurjchem-1645	161	12	):	):	PUNCT
eurjchem-1645	161	13	1.38	1.38	NUM
eurjchem-1645	161	14	(	(	PUNCT
eurjchem-1645	161	15	s	s	PROPN
eurjchem-1645	161	16	,	,	PUNCT
eurjchem-1645	161	17	9	9	NUM
eurjchem-1645	161	18	h	h	NOUN
eurjchem-1645	161	19	,	,	PUNCT
eurjchem-1645	161	20	t‐bu	t‐bu	NOUN
eurjchem-1645	161	21	)	)	PUNCT
eurjchem-1645	161	22	,	,	PUNCT
eurjchem-1645	161	23	2.33	2.33	NUM
eurjchem-1645	161	24	(	(	PUNCT
eurjchem-1645	161	25	d	d	NOUN
eurjchem-1645	161	26	,	,	PUNCT
eurjchem-1645	161	27	2h	2h	NUM
eurjchem-1645	161	28	,	,	PUNCT
eurjchem-1645	161	29	j	j	PROPN
eurjchem-1645	161	30	=	=	PROPN
eurjchem-1645	161	31	6.4	6.4	NUM
eurjchem-1645	161	32	hz	hz	NOUN
eurjchem-1645	161	33	,	,	PUNCT
eurjchem-1645	161	34	ch2	ch2	PROPN
eurjchem-1645	161	35	)	)	PUNCT
eurjchem-1645	161	36	,	,	PUNCT
eurjchem-1645	161	37	2.67	2.67	NUM
eurjchem-1645	161	38	(	(	PUNCT
eurjchem-1645	161	39	m	m	PROPN
eurjchem-1645	161	40	,	,	PUNCT
eurjchem-1645	161	41	2h	2h	NUM
eurjchem-1645	161	42	,	,	PUNCT
eurjchem-1645	161	43	ch2	ch2	PROPN
eurjchem-1645	161	44	)	)	PUNCT
eurjchem-1645	161	45	,	,	PUNCT
eurjchem-1645	161	46	3.60	3.60	NUM
eurjchem-1645	161	47	(	(	PUNCT
eurjchem-1645	161	48	s	s	PROPN
eurjchem-1645	161	49	,	,	PUNCT
eurjchem-1645	161	50	2h	2h	NUM
eurjchem-1645	161	51	,	,	PUNCT
eurjchem-1645	161	52	ch2	ch2	PROPN
eurjchem-1645	161	53	)	)	PUNCT
eurjchem-1645	161	54	,	,	PUNCT
eurjchem-1645	161	55	3.71	3.71	NUM
eurjchem-1645	161	56	(	(	PUNCT
eurjchem-1645	161	57	s	s	PROPN
eurjchem-1645	161	58	,	,	PUNCT
eurjchem-1645	161	59	2h	2h	NUM
eurjchem-1645	161	60	,	,	PUNCT
eurjchem-1645	161	61	n‐ch2	n‐ch2	PROPN
eurjchem-1645	161	62	)	)	PUNCT
eurjchem-1645	161	63	,	,	PUNCT
eurjchem-1645	161	64	6.65	6.65	NUM
eurjchem-1645	161	65	(	(	PUNCT
eurjchem-1645	161	66	s	s	PROPN
eurjchem-1645	161	67	,	,	PUNCT
eurjchem-1645	161	68	1h	1h	NUM
eurjchem-1645	161	69	,	,	PUNCT
eurjchem-1645	161	70	ar‐	ar‐	PROPN
eurjchem-1645	161	71	h	h	NOUN
eurjchem-1645	161	72	)	)	PUNCT
eurjchem-1645	161	73	,	,	PUNCT
eurjchem-1645	161	74	7.13	7.13	NUM
eurjchem-1645	161	75	(	(	PUNCT
eurjchem-1645	161	76	m	m	PROPN
eurjchem-1645	161	77	,	,	PUNCT
eurjchem-1645	161	78	1h	1h	NUM
eurjchem-1645	161	79	,	,	PUNCT
eurjchem-1645	161	80	ar‐h	ar‐h	NOUN
eurjchem-1645	161	81	)	)	PUNCT
eurjchem-1645	161	82	,	,	PUNCT
eurjchem-1645	161	83	7.18	7.18	NUM
eurjchem-1645	161	84	(	(	PUNCT
eurjchem-1645	161	85	m	m	PROPN
eurjchem-1645	161	86	,	,	PUNCT
eurjchem-1645	161	87	1h	1h	NUM
eurjchem-1645	161	88	,	,	PUNCT
eurjchem-1645	161	89	ar‐h	ar‐h	NOUN
eurjchem-1645	161	90	)	)	PUNCT
eurjchem-1645	161	91	,	,	PUNCT
eurjchem-1645	161	92	7.38‐7.28	7.38‐7.28	NUM
eurjchem-1645	161	93	(	(	PUNCT
eurjchem-1645	161	94	m	m	PROPN
eurjchem-1645	161	95	,	,	PUNCT
eurjchem-1645	161	96	7h	7h	PROPN
eurjchem-1645	161	97	,	,	PUNCT
eurjchem-1645	161	98	ar‐h	ar‐h	NOUN
eurjchem-1645	161	99	)	)	PUNCT
eurjchem-1645	161	100	.	.	PUNCT
eurjchem-1645	162	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	162	2	(	(	PUNCT
eurjchem-1645	162	3	ei	ei	X
eurjchem-1645	162	4	,	,	PUNCT
eurjchem-1645	162	5	m	m	PROPN
eurjchem-1645	162	6	/	/	SYM
eurjchem-1645	162	7	z	z	NOUN
eurjchem-1645	162	8	):	):	PUNCT
eurjchem-1645	162	9	430	430	NUM
eurjchem-1645	162	10	(	(	PUNCT
eurjchem-1645	162	11	m+h	m+h	PROPN
eurjchem-1645	162	12	)	)	PUNCT
eurjchem-1645	162	13	.	.	PUNCT
eurjchem-1645	163	1	anal	anal	PROPN
eurjchem-1645	163	2	.	.	PUNCT
eurjchem-1645	163	3	calcd	calcd	NOUN
eurjchem-1645	163	4	.	.	PUNCT
eurjchem-1645	164	1	for	for	ADP
eurjchem-1645	164	2	c26h27n3o3	c26h27n3o3	PROPN
eurjchem-1645	164	3	:	:	PUNCT
eurjchem-1645	164	4	c	c	X
eurjchem-1645	164	5	,	,	PUNCT
eurjchem-1645	164	6	72.71	72.71	NUM
eurjchem-1645	164	7	;	;	PUNCT
eurjchem-1645	164	8	h	h	NOUN
eurjchem-1645	164	9	,	,	PUNCT
eurjchem-1645	164	10	6.34	6.34	NUM
eurjchem-1645	164	11	;	;	PUNCT
eurjchem-1645	164	12	n	n	CCONJ
eurjchem-1645	164	13	,	,	PUNCT
eurjchem-1645	164	14	9.78	9.78	NUM
eurjchem-1645	164	15	.	.	PUNCT
eurjchem-1645	164	16	found	find	VERB
eurjchem-1645	164	17	:	:	PUNCT
eurjchem-1645	165	1	c	c	X
eurjchem-1645	165	2	,	,	PUNCT
eurjchem-1645	165	3	72.70	72.70	NUM
eurjchem-1645	165	4	;	;	PUNCT
eurjchem-1645	165	5	h	h	NOUN
eurjchem-1645	165	6	,	,	PUNCT
eurjchem-1645	165	7	6.36	6.36	NUM
eurjchem-1645	165	8	;	;	PUNCT
eurjchem-1645	165	9	n	n	CCONJ
eurjchem-1645	165	10	,	,	PUNCT
eurjchem-1645	165	11	9.75	9.75	NUM
eurjchem-1645	165	12	%	%	NOUN
eurjchem-1645	165	13	.	.	PUNCT
eurjchem-1645	166	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	166	2	3‐(benzo[b]thiophen‐2‐yl)‐6‐benzyl‐4	3‐(benzo[b]thiophen‐2‐yl)‐6‐benzyl‐4	NUM
eurjchem-1645	166	3	,	,	PUNCT
eurjchem-1645	166	4	5	5	NUM
eurjchem-1645	166	5	,	,	PUNCT
eurjchem-1645	166	6	6,7‐tetra	6,7‐tetra	NUM
eurjchem-1645	166	7	hydropyrazolo[3,4‐c]pyridine‐1‐carboxylate	hydropyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	166	8	(	(	PUNCT
eurjchem-1645	166	9	10b	10b	NOUN
eurjchem-1645	166	10	):	):	PUNCT
eurjchem-1645	166	11	color	color	NOUN
eurjchem-1645	166	12	:	:	PUNCT
eurjchem-1645	166	13	brown	brown	ADJ
eurjchem-1645	166	14	.	.	PUNCT
eurjchem-1645	166	15	yield	yield	NOUN
eurjchem-1645	166	16	:	:	PUNCT
eurjchem-1645	166	17	81	81	NUM
eurjchem-1645	166	18	%	%	NOUN
eurjchem-1645	166	19	.	.	PUNCT
eurjchem-1645	167	1	m.p	m.p	PROPN
eurjchem-1645	167	2	.	.	PROPN
eurjchem-1645	167	3	:	:	PUNCT
eurjchem-1645	168	1	145‐146	145‐146	NUM
eurjchem-1645	168	2	°	°	PROPN
eurjchem-1645	168	3	c	c	PROPN
eurjchem-1645	168	4	.	.	PUNCT
eurjchem-1645	168	5	1h	1h	NUM
eurjchem-1645	168	6	nmr	nmr	NOUN
eurjchem-1645	168	7	(	(	PUNCT
eurjchem-1645	168	8	400	400	NUM
eurjchem-1645	168	9	mhz	mhz	NOUN
eurjchem-1645	168	10	,	,	PUNCT
eurjchem-1645	168	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	168	12	,	,	PUNCT
eurjchem-1645	168	13	δ	δ	PROPN
eurjchem-1645	168	14	,	,	PUNCT
eurjchem-1645	168	15	ppm	ppm	NOUN
eurjchem-1645	168	16	):	):	PUNCT
eurjchem-1645	168	17	1.39	1.39	NUM
eurjchem-1645	168	18	(	(	PUNCT
eurjchem-1645	168	19	s	s	PROPN
eurjchem-1645	168	20	,	,	PUNCT
eurjchem-1645	168	21	9h	9h	NUM
eurjchem-1645	168	22	,	,	PUNCT
eurjchem-1645	168	23	t‐bu	t‐bu	NOUN
eurjchem-1645	168	24	)	)	PUNCT
eurjchem-1645	168	25	,	,	PUNCT
eurjchem-1645	168	26	2.33	2.33	NUM
eurjchem-1645	168	27	(	(	PUNCT
eurjchem-1645	168	28	d	d	NOUN
eurjchem-1645	168	29	,	,	PUNCT
eurjchem-1645	168	30	2h	2h	NUM
eurjchem-1645	168	31	,	,	PUNCT
eurjchem-1645	168	32	j	j	PROPN
eurjchem-1645	168	33	=	=	PROPN
eurjchem-1645	168	34	6.4	6.4	NUM
eurjchem-1645	168	35	hz	hz	NOUN
eurjchem-1645	168	36	,	,	PUNCT
eurjchem-1645	168	37	ch2	ch2	PROPN
eurjchem-1645	168	38	)	)	PUNCT
eurjchem-1645	168	39	,	,	PUNCT
eurjchem-1645	168	40	2.68	2.68	NUM
eurjchem-1645	168	41	(	(	PUNCT
eurjchem-1645	168	42	m	m	PROPN
eurjchem-1645	168	43	,	,	PUNCT
eurjchem-1645	168	44	2h	2h	NUM
eurjchem-1645	168	45	,	,	PUNCT
eurjchem-1645	168	46	ch2	ch2	PROPN
eurjchem-1645	168	47	)	)	PUNCT
eurjchem-1645	168	48	,	,	PUNCT
eurjchem-1645	168	49	3.61	3.61	NUM
eurjchem-1645	168	50	(	(	PUNCT
eurjchem-1645	168	51	s	s	PROPN
eurjchem-1645	168	52	,	,	PUNCT
eurjchem-1645	168	53	2h	2h	NUM
eurjchem-1645	168	54	,	,	PUNCT
eurjchem-1645	168	55	ch2	ch2	PROPN
eurjchem-1645	168	56	)	)	PUNCT
eurjchem-1645	168	57	,	,	PUNCT
eurjchem-1645	168	58	3.7	3.7	NUM
eurjchem-1645	168	59	(	(	PUNCT
eurjchem-1645	168	60	s	s	PROPN
eurjchem-1645	168	61	,	,	PUNCT
eurjchem-1645	168	62	2h	2h	NUM
eurjchem-1645	168	63	,	,	PUNCT
eurjchem-1645	168	64	n‐ch2	n‐ch2	PROPN
eurjchem-1645	168	65	)	)	PUNCT
eurjchem-1645	168	66	,	,	PUNCT
eurjchem-1645	168	67	7.25	7.25	NUM
eurjchem-1645	168	68	(	(	PUNCT
eurjchem-1645	168	69	s	s	PROPN
eurjchem-1645	168	70	,	,	PUNCT
eurjchem-1645	168	71	1h	1h	NUM
eurjchem-1645	168	72	,	,	PUNCT
eurjchem-1645	168	73	ar‐h	ar‐h	NOUN
eurjchem-1645	168	74	)	)	PUNCT
eurjchem-1645	168	75	,	,	PUNCT
eurjchem-1645	168	76	7.38‐7.28	7.38‐7.28	NUM
eurjchem-1645	168	77	(	(	PUNCT
eurjchem-1645	168	78	m	m	PROPN
eurjchem-1645	168	79	,	,	PUNCT
eurjchem-1645	168	80	7h	7h	PROPN
eurjchem-1645	168	81	,	,	PUNCT
eurjchem-1645	168	82	ar‐h	ar‐h	NOUN
eurjchem-1645	168	83	)	)	PUNCT
eurjchem-1645	168	84	,	,	PUNCT
eurjchem-1645	168	85	7.68‐7.81	7.68‐7.81	NUM
eurjchem-1645	168	86	(	(	PUNCT
eurjchem-1645	168	87	m	m	PROPN
eurjchem-1645	168	88	,	,	PUNCT
eurjchem-1645	168	89	2h	2h	NUM
eurjchem-1645	168	90	,	,	PUNCT
eurjchem-1645	168	91	ar‐h	ar‐h	NOUN
eurjchem-1645	168	92	)	)	PUNCT
eurjchem-1645	168	93	.	.	PUNCT
eurjchem-1645	169	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	169	2	(	(	PUNCT
eurjchem-1645	169	3	ei	ei	X
eurjchem-1645	169	4	,	,	PUNCT
eurjchem-1645	169	5	m	m	PROPN
eurjchem-1645	169	6	/	/	SYM
eurjchem-1645	169	7	z	z	NOUN
eurjchem-1645	169	8	):	):	PUNCT
eurjchem-1645	169	9	446	446	NUM
eurjchem-1645	169	10	(	(	PUNCT
eurjchem-1645	169	11	m+h	m+h	NOUN
eurjchem-1645	169	12	)	)	PUNCT
eurjchem-1645	169	13	.	.	PUNCT
eurjchem-1645	170	1	anal	anal	PROPN
eurjchem-1645	170	2	.	.	PUNCT
eurjchem-1645	170	3	calcd	calcd	NOUN
eurjchem-1645	170	4	.	.	PUNCT
eurjchem-1645	171	1	for	for	ADP
eurjchem-1645	171	2	c26h27	c26h27	NOUN
eurjchem-1645	171	3	n3o2s	n3o2s	NUM
eurjchem-1645	171	4	:	:	PUNCT
eurjchem-1645	171	5	c	c	X
eurjchem-1645	171	6	,	,	PUNCT
eurjchem-1645	171	7	70.09	70.09	NUM
eurjchem-1645	171	8	;	;	PUNCT
eurjchem-1645	171	9	h	h	NOUN
eurjchem-1645	171	10	,	,	PUNCT
eurjchem-1645	171	11	6.11	6.11	NUM
eurjchem-1645	171	12	;	;	PUNCT
eurjchem-1645	171	13	n	n	CCONJ
eurjchem-1645	171	14	,	,	PUNCT
eurjchem-1645	171	15	9.43	9.43	NUM
eurjchem-1645	171	16	.	.	PUNCT
eurjchem-1645	171	17	found	find	VERB
eurjchem-1645	171	18	:	:	PUNCT
eurjchem-1645	172	1	c	c	X
eurjchem-1645	172	2	,	,	PUNCT
eurjchem-1645	172	3	70.06	70.06	NUM
eurjchem-1645	172	4	;	;	PUNCT
eurjchem-1645	172	5	h	h	NOUN
eurjchem-1645	172	6	,	,	PUNCT
eurjchem-1645	172	7	6.13	6.13	NUM
eurjchem-1645	172	8	;	;	PUNCT
eurjchem-1645	172	9	n	n	CCONJ
eurjchem-1645	172	10	,	,	PUNCT
eurjchem-1645	172	11	9.41	9.41	NUM
eurjchem-1645	172	12	%	%	NOUN
eurjchem-1645	172	13	.	.	PUNCT
eurjchem-1645	173	1	tert‐butyl	tert‐butyl	ADP
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eurjchem-1645	173	3	zolo[3,4‐c]pyridine‐1‐carboxylate	zolo[3,4‐c]pyridine‐1‐carboxylate	PROPN
eurjchem-1645	173	4	(	(	PUNCT
eurjchem-1645	173	5	10c	10c	NUM
eurjchem-1645	173	6	):	):	PUNCT
eurjchem-1645	173	7	color	color	NOUN
eurjchem-1645	173	8	:	:	PUNCT
eurjchem-1645	173	9	brown	brown	ADJ
eurjchem-1645	173	10	.	.	PUNCT
eurjchem-1645	174	1	yield	yield	NOUN
eurjchem-1645	174	2	:	:	PUNCT
eurjchem-1645	174	3	63	63	NUM
eurjchem-1645	174	4	%	%	NOUN
eurjchem-1645	174	5	.	.	PUNCT
eurjchem-1645	175	1	m.p	m.p	PROPN
eurjchem-1645	175	2	.	.	PROPN
eurjchem-1645	175	3	:	:	PUNCT
eurjchem-1645	176	1	154‐155	154‐155	NUM
eurjchem-1645	176	2	°	°	PROPN
eurjchem-1645	176	3	c	c	PROPN
eurjchem-1645	176	4	.	.	PUNCT
eurjchem-1645	176	5	1h	1h	NUM
eurjchem-1645	176	6	nmr	nmr	NOUN
eurjchem-1645	176	7	(	(	PUNCT
eurjchem-1645	176	8	400	400	NUM
eurjchem-1645	176	9	mhz	mhz	NOUN
eurjchem-1645	176	10	,	,	PUNCT
eurjchem-1645	176	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	176	12	,	,	PUNCT
eurjchem-1645	176	13	δ	δ	PROPN
eurjchem-1645	176	14	,	,	PUNCT
eurjchem-1645	176	15	ppm	ppm	NOUN
eurjchem-1645	176	16	):	):	PUNCT
eurjchem-1645	176	17	1.39	1.39	NUM
eurjchem-1645	176	18	(	(	PUNCT
eurjchem-1645	176	19	s	s	PROPN
eurjchem-1645	176	20	,	,	PUNCT
eurjchem-1645	176	21	9h	9h	NUM
eurjchem-1645	176	22	,	,	PUNCT
eurjchem-1645	176	23	t‐bu	t‐bu	NOUN
eurjchem-1645	176	24	)	)	PUNCT
eurjchem-1645	176	25	,	,	PUNCT
eurjchem-1645	176	26	2.35	2.35	NUM
eurjchem-1645	176	27	(	(	PUNCT
eurjchem-1645	176	28	d	d	PROPN
eurjchem-1645	176	29	,	,	PUNCT
eurjchem-1645	176	30	2h	2h	NUM
eurjchem-1645	176	31	,	,	PUNCT
eurjchem-1645	176	32	j	j	PROPN
eurjchem-1645	176	33	=	=	PROPN
eurjchem-1645	176	34	6.4	6.4	NUM
eurjchem-1645	176	35	hz	hz	NOUN
eurjchem-1645	176	36	,	,	PUNCT
eurjchem-1645	176	37	ch2	ch2	PROPN
eurjchem-1645	176	38	)	)	PUNCT
eurjchem-1645	176	39	,	,	PUNCT
eurjchem-1645	176	40	2.67	2.67	NUM
eurjchem-1645	176	41	(	(	PUNCT
eurjchem-1645	176	42	m	m	PROPN
eurjchem-1645	176	43	,	,	PUNCT
eurjchem-1645	176	44	2h	2h	NUM
eurjchem-1645	176	45	,	,	PUNCT
eurjchem-1645	176	46	ch2	ch2	PROPN
eurjchem-1645	176	47	)	)	PUNCT
eurjchem-1645	176	48	,	,	PUNCT
eurjchem-1645	176	49	3.61	3.61	NUM
eurjchem-1645	176	50	(	(	PUNCT
eurjchem-1645	176	51	s	s	PROPN
eurjchem-1645	176	52	,	,	PUNCT
eurjchem-1645	176	53	2h	2h	NUM
eurjchem-1645	176	54	,	,	PUNCT
eurjchem-1645	176	55	ch2	ch2	PROPN
eurjchem-1645	176	56	)	)	PUNCT
eurjchem-1645	176	57	,	,	PUNCT
eurjchem-1645	176	58	3.70	3.70	NUM
eurjchem-1645	176	59	(	(	PUNCT
eurjchem-1645	176	60	s	s	PROPN
eurjchem-1645	176	61	,	,	PUNCT
eurjchem-1645	176	62	2h	2h	NUM
eurjchem-1645	176	63	,	,	PUNCT
eurjchem-1645	176	64	n‐ch2	n‐ch2	PROPN
eurjchem-1645	176	65	)	)	PUNCT
eurjchem-1645	176	66	,	,	PUNCT
eurjchem-1645	176	67	7.38‐7.28	7.38‐7.28	NUM
eurjchem-1645	176	68	(	(	PUNCT
eurjchem-1645	176	69	m	m	PROPN
eurjchem-1645	176	70	,	,	PUNCT
eurjchem-1645	176	71	5h	5h	NUM
eurjchem-1645	176	72	,	,	PUNCT
eurjchem-1645	176	73	ar‐h	ar‐h	NOUN
eurjchem-1645	176	74	)	)	PUNCT
eurjchem-1645	176	75	,	,	PUNCT
eurjchem-1645	176	76	7.66‐7.45	7.66‐7.45	NUM
eurjchem-1645	176	77	(	(	PUNCT
eurjchem-1645	176	78	m	m	PROPN
eurjchem-1645	176	79	,	,	PUNCT
eurjchem-1645	176	80	3h	3h	NUM
eurjchem-1645	176	81	,	,	PUNCT
eurjchem-1645	176	82	ar‐h	ar‐h	NOUN
eurjchem-1645	176	83	)	)	PUNCT
eurjchem-1645	176	84	,	,	PUNCT
eurjchem-1645	176	85	8.19‐8.02	8.19‐8.02	PROPN
eurjchem-1645	176	86	(	(	PUNCT
eurjchem-1645	176	87	m	m	PROPN
eurjchem-1645	176	88	,	,	PUNCT
eurjchem-1645	176	89	2h	2h	NUM
eurjchem-1645	176	90	,	,	PUNCT
eurjchem-1645	176	91	ar‐h	ar‐h	NOUN
eurjchem-1645	176	92	)	)	PUNCT
eurjchem-1645	176	93	,	,	PUNCT
eurjchem-1645	176	94	8.78	8.78	NUM
eurjchem-1645	176	95	(	(	PUNCT
eurjchem-1645	176	96	s	s	PROPN
eurjchem-1645	176	97	,	,	PUNCT
eurjchem-1645	176	98	1h	1h	NUM
eurjchem-1645	176	99	,	,	PUNCT
eurjchem-1645	176	100	ar‐h	ar‐h	NOUN
eurjchem-1645	176	101	)	)	PUNCT
eurjchem-1645	176	102	.	.	PUNCT
eurjchem-1645	177	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	177	2	(	(	PUNCT
eurjchem-1645	177	3	ei	ei	X
eurjchem-1645	177	4	,	,	PUNCT
eurjchem-1645	177	5	m	m	PROPN
eurjchem-1645	177	6	/	/	SYM
eurjchem-1645	177	7	z	z	NOUN
eurjchem-1645	177	8	):	):	PUNCT
eurjchem-1645	177	9	441	441	NUM
eurjchem-1645	177	10	(	(	PUNCT
eurjchem-1645	177	11	m+h	m+h	NOUN
eurjchem-1645	177	12	)	)	PUNCT
eurjchem-1645	177	13	.	.	PUNCT
eurjchem-1645	178	1	anal	anal	PROPN
eurjchem-1645	178	2	.	.	PUNCT
eurjchem-1645	178	3	calcd	calcd	NOUN
eurjchem-1645	178	4	.	.	PUNCT
eurjchem-1645	179	1	for	for	ADP
eurjchem-1645	179	2	c27h28n4o2	c27h28n4o2	ADJ
eurjchem-1645	179	3	:	:	PUNCT
eurjchem-1645	179	4	c	c	X
eurjchem-1645	179	5	,	,	PUNCT
eurjchem-1645	179	6	73.61	73.61	NUM
eurjchem-1645	179	7	;	;	PUNCT
eurjchem-1645	179	8	h	h	NOUN
eurjchem-1645	179	9	,	,	PUNCT
eurjchem-1645	179	10	6.41	6.41	NUM
eurjchem-1645	179	11	;	;	PUNCT
eurjchem-1645	179	12	n	n	CCONJ
eurjchem-1645	179	13	,	,	PUNCT
eurjchem-1645	179	14	12.72	12.72	NUM
eurjchem-1645	179	15	.	.	PUNCT
eurjchem-1645	179	16	found	find	VERB
eurjchem-1645	179	17	:	:	PUNCT
eurjchem-1645	180	1	c	c	X
eurjchem-1645	180	2	,	,	PUNCT
eurjchem-1645	180	3	73.64	73.64	NUM
eurjchem-1645	180	4	;	;	PUNCT
eurjchem-1645	180	5	h	h	NOUN
eurjchem-1645	180	6	,	,	PUNCT
eurjchem-1645	180	7	6.39	6.39	NUM
eurjchem-1645	180	8	;	;	PUNCT
eurjchem-1645	180	9	n	n	CCONJ
eurjchem-1645	180	10	,	,	PUNCT
eurjchem-1645	180	11	12.74	12.74	NUM
eurjchem-1645	180	12	%	%	NOUN
eurjchem-1645	180	13	.	.	PUNCT
eurjchem-1645	181	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	181	2	6‐benzyl‐4,5,6,7‐tetrahydro‐3‐(quinolin‐5‐yl)pyra	6‐benzyl‐4,5,6,7‐tetrahydro‐3‐(quinolin‐5‐yl)pyra	NUM
eurjchem-1645	181	3	zolo[3,4‐c]pyridine‐1‐carboxylate	zolo[3,4‐c]pyridine‐1‐carboxylate	X
eurjchem-1645	181	4	(	(	PUNCT
eurjchem-1645	181	5	10d	10d	NUM
eurjchem-1645	181	6	):	):	PUNCT
eurjchem-1645	181	7	color	color	NOUN
eurjchem-1645	181	8	:	:	PUNCT
eurjchem-1645	181	9	brown	brown	ADJ
eurjchem-1645	181	10	.	.	PUNCT
eurjchem-1645	181	11	yield	yield	NOUN
eurjchem-1645	181	12	:	:	PUNCT
eurjchem-1645	181	13	66	66	NUM
eurjchem-1645	181	14	%	%	NOUN
eurjchem-1645	181	15	.	.	PUNCT
eurjchem-1645	182	1	m.p	m.p	PROPN
eurjchem-1645	182	2	.	.	PROPN
eurjchem-1645	182	3	:	:	PUNCT
eurjchem-1645	183	1	161‐162	161‐162	NUM
eurjchem-1645	183	2	°	°	SYM
eurjchem-1645	183	3	c	c	X
eurjchem-1645	183	4	.	.	PUNCT
eurjchem-1645	184	1	1h	1h	NUM
eurjchem-1645	184	2	nmr	nmr	NOUN
eurjchem-1645	184	3	(	(	PUNCT
eurjchem-1645	184	4	400	400	NUM
eurjchem-1645	184	5	mhz	mhz	NOUN
eurjchem-1645	184	6	,	,	PUNCT
eurjchem-1645	184	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	184	8	,	,	PUNCT
eurjchem-1645	184	9	δ	δ	PROPN
eurjchem-1645	184	10	,	,	PUNCT
eurjchem-1645	184	11	ppm	ppm	NOUN
eurjchem-1645	184	12	):	):	PUNCT
eurjchem-1645	184	13	1.39	1.39	NUM
eurjchem-1645	184	14	(	(	PUNCT
eurjchem-1645	184	15	s	s	PROPN
eurjchem-1645	184	16	,	,	PUNCT
eurjchem-1645	184	17	9h	9h	NUM
eurjchem-1645	184	18	,	,	PUNCT
eurjchem-1645	184	19	t‐bu	t‐bu	NOUN
eurjchem-1645	184	20	)	)	PUNCT
eurjchem-1645	184	21	,	,	PUNCT
eurjchem-1645	184	22	2.33	2.33	NUM
eurjchem-1645	184	23	(	(	PUNCT
eurjchem-1645	184	24	d	d	NOUN
eurjchem-1645	184	25	,	,	PUNCT
eurjchem-1645	184	26	2h	2h	NUM
eurjchem-1645	184	27	,	,	PUNCT
eurjchem-1645	184	28	j	j	PROPN
eurjchem-1645	184	29	=	=	PROPN
eurjchem-1645	184	30	6.4	6.4	NUM
eurjchem-1645	184	31	hz	hz	NOUN
eurjchem-1645	184	32	,	,	PUNCT
eurjchem-1645	184	33	ch2	ch2	PROPN
eurjchem-1645	184	34	)	)	PUNCT
eurjchem-1645	184	35	,	,	PUNCT
eurjchem-1645	184	36	2.68	2.68	NUM
eurjchem-1645	184	37	(	(	PUNCT
eurjchem-1645	184	38	m	m	PROPN
eurjchem-1645	184	39	,	,	PUNCT
eurjchem-1645	184	40	2h	2h	NUM
eurjchem-1645	184	41	,	,	PUNCT
eurjchem-1645	184	42	ch2	ch2	PROPN
eurjchem-1645	184	43	)	)	PUNCT
eurjchem-1645	184	44	,	,	PUNCT
eurjchem-1645	184	45	3.61	3.61	NUM
eurjchem-1645	184	46	(	(	PUNCT
eurjchem-1645	184	47	s	s	PROPN
eurjchem-1645	184	48	,	,	PUNCT
eurjchem-1645	184	49	2h	2h	NUM
eurjchem-1645	184	50	,	,	PUNCT
eurjchem-1645	184	51	ch2	ch2	PROPN
eurjchem-1645	184	52	)	)	PUNCT
eurjchem-1645	184	53	,	,	PUNCT
eurjchem-1645	184	54	3.70	3.70	NUM
eurjchem-1645	184	55	(	(	PUNCT
eurjchem-1645	184	56	s	s	PROPN
eurjchem-1645	184	57	,	,	PUNCT
eurjchem-1645	184	58	2h	2h	NUM
eurjchem-1645	184	59	,	,	PUNCT
eurjchem-1645	184	60	n‐ch2	n‐ch2	PROPN
eurjchem-1645	184	61	)	)	PUNCT
eurjchem-1645	184	62	,	,	PUNCT
eurjchem-1645	184	63	7.38‐7.21	7.38‐7.21	PROPN
eurjchem-1645	184	64	(	(	PUNCT
eurjchem-1645	184	65	m	m	PROPN
eurjchem-1645	184	66	,	,	PUNCT
eurjchem-1645	184	67	5h	5h	NUM
eurjchem-1645	184	68	,	,	PUNCT
eurjchem-1645	184	69	ar‐h	ar‐h	NOUN
eurjchem-1645	184	70	)	)	PUNCT
eurjchem-1645	184	71	,	,	PUNCT
eurjchem-1645	184	72	7.66‐7.45	7.66‐7.45	NUM
eurjchem-1645	184	73	(	(	PUNCT
eurjchem-1645	184	74	m	m	PROPN
eurjchem-1645	184	75	,	,	PUNCT
eurjchem-1645	184	76	3h	3h	NUM
eurjchem-1645	184	77	,	,	PUNCT
eurjchem-1645	184	78	ar‐h	ar‐h	NOUN
eurjchem-1645	184	79	)	)	PUNCT
eurjchem-1645	184	80	,	,	PUNCT
eurjchem-1645	184	81	8.19‐8.02	8.19‐8.02	PROPN
eurjchem-1645	184	82	(	(	PUNCT
eurjchem-1645	184	83	m	m	PROPN
eurjchem-1645	184	84	,	,	PUNCT
eurjchem-1645	184	85	2h	2h	NUM
eurjchem-1645	184	86	,	,	PUNCT
eurjchem-1645	184	87	ar‐h	ar‐h	NOUN
eurjchem-1645	184	88	)	)	PUNCT
eurjchem-1645	184	89	,	,	PUNCT
eurjchem-1645	184	90	8.78	8.78	NUM
eurjchem-1645	184	91	(	(	PUNCT
eurjchem-1645	184	92	s	s	PROPN
eurjchem-1645	184	93	,	,	PUNCT
eurjchem-1645	184	94	1h	1h	NUM
eurjchem-1645	184	95	,	,	PUNCT
eurjchem-1645	184	96	ar‐h	ar‐h	NOUN
eurjchem-1645	184	97	)	)	PUNCT
eurjchem-1645	184	98	.	.	PUNCT
eurjchem-1645	185	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	185	2	(	(	PUNCT
eurjchem-1645	185	3	ei	ei	X
eurjchem-1645	185	4	,	,	PUNCT
eurjchem-1645	185	5	m	m	PROPN
eurjchem-1645	185	6	/	/	SYM
eurjchem-1645	185	7	z	z	NOUN
eurjchem-1645	185	8	):	):	PUNCT
eurjchem-1645	185	9	441	441	NUM
eurjchem-1645	185	10	(	(	PUNCT
eurjchem-1645	185	11	m+h	m+h	NOUN
eurjchem-1645	185	12	)	)	PUNCT
eurjchem-1645	185	13	.	.	PUNCT
eurjchem-1645	186	1	anal	anal	PROPN
eurjchem-1645	186	2	.	.	PUNCT
eurjchem-1645	186	3	calcd	calcd	NOUN
eurjchem-1645	186	4	.	.	PUNCT
eurjchem-1645	187	1	for	for	ADP
eurjchem-1645	187	2	c27h28n4o2	c27h28n4o2	ADJ
eurjchem-1645	187	3	:	:	PUNCT
eurjchem-1645	187	4	c	c	X
eurjchem-1645	187	5	,	,	PUNCT
eurjchem-1645	187	6	73.61	73.61	NUM
eurjchem-1645	187	7	;	;	PUNCT
eurjchem-1645	187	8	h	h	NOUN
eurjchem-1645	187	9	,	,	PUNCT
eurjchem-1645	187	10	6.41	6.41	NUM
eurjchem-1645	187	11	;	;	PUNCT
eurjchem-1645	187	12	n	n	CCONJ
eurjchem-1645	187	13	,	,	PUNCT
eurjchem-1645	187	14	12.72	12.72	NUM
eurjchem-1645	187	15	.	.	PUNCT
eurjchem-1645	187	16	found	find	VERB
eurjchem-1645	187	17	:	:	PUNCT
eurjchem-1645	188	1	c	c	X
eurjchem-1645	188	2	,	,	PUNCT
eurjchem-1645	188	3	73.63	73.63	NUM
eurjchem-1645	188	4	;	;	PUNCT
eurjchem-1645	188	5	h	h	NOUN
eurjchem-1645	188	6	,	,	PUNCT
eurjchem-1645	188	7	6.42	6.42	NUM
eurjchem-1645	188	8	;	;	PUNCT
eurjchem-1645	188	9	n	n	CCONJ
eurjchem-1645	188	10	,	,	PUNCT
eurjchem-1645	188	11	12.73	12.73	NUM
eurjchem-1645	188	12	%	%	NOUN
eurjchem-1645	188	13	.	.	PUNCT
eurjchem-1645	189	1	2.2.10	2.2.10	NUM
eurjchem-1645	189	2	.	.	PUNCT
eurjchem-1645	189	3	general	general	ADJ
eurjchem-1645	189	4	procedure	procedure	NOUN
eurjchem-1645	189	5	for	for	ADP
eurjchem-1645	189	6	synthesis	synthesis	NOUN
eurjchem-1645	189	7	of	of	ADP
eurjchem-1645	189	8	compounds	compound	NOUN
eurjchem-1645	189	9	(	(	PUNCT
eurjchem-1645	189	10	11a‐	11a‐	NUM
eurjchem-1645	189	11	d	d	NOUN
eurjchem-1645	189	12	)	)	PUNCT
eurjchem-1645	189	13	,	,	PUNCT
eurjchem-1645	189	14	step	step	NOUN
eurjchem-1645	189	15	(	(	PUNCT
eurjchem-1645	189	16	j	j	NOUN
eurjchem-1645	189	17	)	)	PUNCT
eurjchem-1645	189	18	to	to	ADP
eurjchem-1645	189	19	a	a	DET
eurjchem-1645	189	20	stirred	stir	VERB
eurjchem-1645	189	21	solution	solution	NOUN
eurjchem-1645	189	22	of	of	ADP
eurjchem-1645	189	23	compounds	compound	NOUN
eurjchem-1645	189	24	10a‐d	10a‐d	NOUN
eurjchem-1645	189	25	(	(	PUNCT
eurjchem-1645	189	26	1	1	NUM
eurjchem-1645	189	27	mmol	mmol	NOUN
eurjchem-1645	189	28	)	)	PUNCT
eurjchem-1645	189	29	in	in	ADP
eurjchem-1645	189	30	methanol	methanol	NOUN
eurjchem-1645	189	31	(	(	PUNCT
eurjchem-1645	189	32	10	10	NUM
eurjchem-1645	189	33	ml	ml	NOUN
eurjchem-1645	189	34	)	)	PUNCT
eurjchem-1645	189	35	was	be	AUX
eurjchem-1645	189	36	added	add	VERB
eurjchem-1645	189	37	palladium	palladium	NOUN
eurjchem-1645	189	38	on	on	ADP
eurjchem-1645	189	39	carbon	carbon	NOUN
eurjchem-1645	189	40	(	(	PUNCT
eurjchem-1645	189	41	10	10	NUM
eurjchem-1645	189	42	mol%	mol%	NOUN
eurjchem-1645	189	43	)	)	PUNCT
eurjchem-1645	189	44	and	and	CCONJ
eurjchem-1645	189	45	keep	keep	VERB
eurjchem-1645	189	46	the	the	DET
eurjchem-1645	189	47	reaction	reaction	NOUN
eurjchem-1645	189	48	in	in	ADP
eurjchem-1645	189	49	parr	parr	ADJ
eurjchem-1645	189	50	shaker	shaker	NOUN
eurjchem-1645	189	51	apparatus	apparatus	NOUN
eurjchem-1645	189	52	by	by	ADP
eurjchem-1645	189	53	applying	apply	VERB
eurjchem-1645	189	54	hydrogen	hydrogen	NOUN
eurjchem-1645	189	55	gas	gas	NOUN
eurjchem-1645	189	56	pressure	pressure	NOUN
eurjchem-1645	189	57	of	of	ADP
eurjchem-1645	189	58	50	50	NUM
eurjchem-1645	189	59	psi	psi	NOUN
eurjchem-1645	189	60	for	for	ADP
eurjchem-1645	189	61	3	3	NUM
eurjchem-1645	189	62	h	h	NOUN
eurjchem-1645	189	63	at	at	ADP
eurjchem-1645	189	64	room	room	NOUN
eurjchem-1645	189	65	temperature	temperature	NOUN
eurjchem-1645	189	66	.	.	PUNCT
eurjchem-1645	190	1	progress	progress	NOUN
eurjchem-1645	190	2	of	of	ADP
eurjchem-1645	190	3	reaction	reaction	NOUN
eurjchem-1645	190	4	was	be	AUX
eurjchem-1645	190	5	monitored	monitor	VERB
eurjchem-1645	190	6	by	by	ADP
eurjchem-1645	190	7	lc‐ms	lc‐ms	PRON
eurjchem-1645	190	8	for	for	ADP
eurjchem-1645	190	9	the	the	DET
eurjchem-1645	190	10	con‐	con‐	NOUN
eurjchem-1645	190	11	sumption	sumption	NOUN
eurjchem-1645	190	12	of	of	ADP
eurjchem-1645	190	13	starting	start	VERB
eurjchem-1645	190	14	material	material	NOUN
eurjchem-1645	190	15	.	.	PUNCT
eurjchem-1645	191	1	after	after	ADP
eurjchem-1645	191	2	completion	completion	NOUN
eurjchem-1645	191	3	the	the	DET
eurjchem-1645	191	4	reaction	reaction	NOUN
eurjchem-1645	191	5	,	,	PUNCT
eurjchem-1645	191	6	the	the	DET
eurjchem-1645	191	7	reaction	reaction	NOUN
eurjchem-1645	191	8	mixtures	mixture	NOUN
eurjchem-1645	191	9	filtered	filter	VERB
eurjchem-1645	191	10	through	through	ADP
eurjchem-1645	191	11	a	a	DET
eurjchem-1645	191	12	pad	pad	NOUN
eurjchem-1645	191	13	of	of	ADP
eurjchem-1645	191	14	celite	celite	ADJ
eurjchem-1645	191	15	and	and	CCONJ
eurjchem-1645	191	16	obtain	obtain	VERB
eurjchem-1645	191	17	filtrate	filtrate	NOUN
eurjchem-1645	191	18	evaporated	evaporate	VERB
eurjchem-1645	191	19	under	under	ADP
eurjchem-1645	191	20	reduced	reduced	ADJ
eurjchem-1645	191	21	pressure	pressure	NOUN
eurjchem-1645	191	22	to	to	PART
eurjchem-1645	191	23	obtain	obtain	VERB
eurjchem-1645	191	24	crude	crude	ADJ
eurjchem-1645	191	25	semisolid	semisolid	NOUN
eurjchem-1645	191	26	material	material	NOUN
eurjchem-1645	191	27	for	for	ADP
eurjchem-1645	191	28	compound	compound	NOUN
eurjchem-1645	191	29	11a‐h	11a‐h	PROPN
eurjchem-1645	191	30	.	.	PUNCT
eurjchem-1645	192	1	the	the	DET
eurjchem-1645	192	2	obtained	obtain	VERB
eurjchem-1645	192	3	crude	crude	NOUN
eurjchem-1645	192	4	was	be	AUX
eurjchem-1645	192	5	washed	wash	VERB
eurjchem-1645	192	6	with	with	ADP
eurjchem-1645	192	7	cold	cold	ADJ
eurjchem-1645	192	8	pentane	pentane	NOUN
eurjchem-1645	192	9	and	and	CCONJ
eurjchem-1645	192	10	cold	cold	ADJ
eurjchem-1645	192	11	diethyl	diethyl	NOUN
eurjchem-1645	192	12	ether	ether	NOUN
eurjchem-1645	192	13	to	to	PART
eurjchem-1645	192	14	obtain	obtain	VERB
eurjchem-1645	192	15	solid	solid	ADJ
eurjchem-1645	192	16	compounds	compound	NOUN
eurjchem-1645	192	17	11a‐h	11a‐h	ADJ
eurjchem-1645	192	18	.	.	PUNCT
eurjchem-1645	193	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	193	2	3‐(benzofuran‐2‐yl)‐4	3‐(benzofuran‐2‐yl)‐4	NUM
eurjchem-1645	193	3	,	,	PUNCT
eurjchem-1645	193	4	5	5	NUM
eurjchem-1645	193	5	,	,	PUNCT
eurjchem-1645	193	6	6	6	NUM
eurjchem-1645	193	7	,	,	PUNCT
eurjchem-1645	194	1	7‐tetrahydropyrazolo	7‐tetrahydropyrazolo	NOUN
eurjchem-1645	195	1	[	[	X
eurjchem-1645	195	2	3,4‐c]pyridine‐1‐carboxylate	3,4‐c]pyridine‐1‐carboxylate	NUM
eurjchem-1645	195	3	(	(	PUNCT
eurjchem-1645	195	4	11a	11a	NUM
eurjchem-1645	195	5	):	):	PUNCT
eurjchem-1645	195	6	color	color	NOUN
eurjchem-1645	195	7	:	:	PUNCT
eurjchem-1645	195	8	brown	brown	ADJ
eurjchem-1645	195	9	.	.	PUNCT
eurjchem-1645	196	1	yield	yield	NOUN
eurjchem-1645	196	2	:	:	PUNCT
eurjchem-1645	196	3	87	87	NUM
eurjchem-1645	196	4	%	%	NOUN
eurjchem-1645	196	5	.	.	PUNCT
eurjchem-1645	197	1	m.p	m.p	PROPN
eurjchem-1645	197	2	.	.	PROPN
eurjchem-1645	197	3	:	:	PUNCT
eurjchem-1645	198	1	115‐116	115‐116	NUM
eurjchem-1645	198	2	°	°	SYM
eurjchem-1645	198	3	c	c	X
eurjchem-1645	198	4	.	.	PUNCT
eurjchem-1645	199	1	1h	1h	NUM
eurjchem-1645	199	2	nmr	nmr	NOUN
eurjchem-1645	199	3	(	(	PUNCT
eurjchem-1645	199	4	400	400	NUM
eurjchem-1645	199	5	mhz	mhz	NOUN
eurjchem-1645	199	6	,	,	PUNCT
eurjchem-1645	199	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	199	8	,	,	PUNCT
eurjchem-1645	199	9	δ	δ	PROPN
eurjchem-1645	199	10	,	,	PUNCT
eurjchem-1645	199	11	ppm	ppm	NOUN
eurjchem-1645	199	12	):	):	PUNCT
eurjchem-1645	199	13	1.39	1.39	NUM
eurjchem-1645	199	14	(	(	PUNCT
eurjchem-1645	199	15	s	s	PROPN
eurjchem-1645	199	16	,	,	PUNCT
eurjchem-1645	199	17	9h	9h	NUM
eurjchem-1645	199	18	,	,	PUNCT
eurjchem-1645	199	19	t‐bu	t‐bu	NOUN
eurjchem-1645	199	20	)	)	PUNCT
eurjchem-1645	199	21	,	,	PUNCT
eurjchem-1645	199	22	2.33	2.33	NUM
eurjchem-1645	199	23	(	(	PUNCT
eurjchem-1645	199	24	d	d	NOUN
eurjchem-1645	199	25	,	,	PUNCT
eurjchem-1645	199	26	2h	2h	NUM
eurjchem-1645	199	27	,	,	PUNCT
eurjchem-1645	199	28	j	j	PROPN
eurjchem-1645	199	29	=	=	PROPN
eurjchem-1645	199	30	6.4	6.4	NUM
eurjchem-1645	199	31	hz	hz	NOUN
eurjchem-1645	199	32	,	,	PUNCT
eurjchem-1645	199	33	ch2	ch2	PROPN
eurjchem-1645	199	34	)	)	PUNCT
eurjchem-1645	199	35	,	,	PUNCT
eurjchem-1645	199	36	2.67	2.67	NUM
eurjchem-1645	199	37	(	(	PUNCT
eurjchem-1645	199	38	m	m	PROPN
eurjchem-1645	199	39	,	,	PUNCT
eurjchem-1645	199	40	2h	2h	NUM
eurjchem-1645	199	41	,	,	PUNCT
eurjchem-1645	199	42	ch2	ch2	PROPN
eurjchem-1645	199	43	)	)	PUNCT
eurjchem-1645	199	44	,	,	PUNCT
eurjchem-1645	199	45	3.60	3.60	NUM
eurjchem-1645	199	46	(	(	PUNCT
eurjchem-1645	199	47	s	s	PROPN
eurjchem-1645	199	48	,	,	PUNCT
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eurjchem-1645	199	50	,	,	PUNCT
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eurjchem-1645	199	53	,	,	PUNCT
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eurjchem-1645	199	67	1h	1h	NUM
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eurjchem-1645	199	71	,	,	PUNCT
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eurjchem-1645	199	75	,	,	PUNCT
eurjchem-1645	199	76	1h	1h	NUM
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eurjchem-1645	199	80	,	,	PUNCT
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eurjchem-1645	199	84	,	,	PUNCT
eurjchem-1645	199	85	2h	2h	NUM
eurjchem-1645	199	86	,	,	PUNCT
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eurjchem-1645	200	9	340	340	NUM
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eurjchem-1645	200	11	m+h	m+h	NOUN
eurjchem-1645	200	12	)	)	PUNCT
eurjchem-1645	200	13	.	.	PUNCT
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eurjchem-1645	201	4	.	.	PUNCT
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eurjchem-1645	202	5	,	,	PUNCT
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eurjchem-1645	202	10	6.24	6.24	NUM
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eurjchem-1645	202	13	,	,	PUNCT
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eurjchem-1645	202	17	:	:	PUNCT
eurjchem-1645	203	1	c	c	X
eurjchem-1645	203	2	,	,	PUNCT
eurjchem-1645	203	3	67.22	67.22	NUM
eurjchem-1645	203	4	;	;	PUNCT
eurjchem-1645	203	5	h	h	NOUN
eurjchem-1645	203	6	,	,	PUNCT
eurjchem-1645	203	7	6.21	6.21	NUM
eurjchem-1645	203	8	;	;	PUNCT
eurjchem-1645	203	9	n	n	CCONJ
eurjchem-1645	203	10	,	,	PUNCT
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eurjchem-1645	203	13	.	.	PUNCT
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eurjchem-1645	204	2	3‐(benzo[b]thiophen‐2‐yl)‐4	3‐(benzo[b]thiophen‐2‐yl)‐4	NUM
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eurjchem-1645	204	4	5	5	NUM
eurjchem-1645	204	5	,	,	PUNCT
eurjchem-1645	204	6	6	6	NUM
eurjchem-1645	204	7	,	,	PUNCT
eurjchem-1645	204	8	7‐tetrahydro	7‐tetrahydro	NUM
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eurjchem-1645	204	10	(	(	PUNCT
eurjchem-1645	204	11	11b	11b	NOUN
eurjchem-1645	204	12	):	):	PUNCT
eurjchem-1645	204	13	color	color	NOUN
eurjchem-1645	204	14	:	:	PUNCT
eurjchem-1645	204	15	yellow	yellow	ADJ
eurjchem-1645	204	16	.	.	PUNCT
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eurjchem-1645	205	2	:	:	PUNCT
eurjchem-1645	205	3	90	90	NUM
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eurjchem-1645	205	5	.	.	PUNCT
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eurjchem-1645	206	2	.	.	PROPN
eurjchem-1645	206	3	:	:	PUNCT
eurjchem-1645	207	1	121‐122	121‐122	NUM
eurjchem-1645	207	2	°	°	SYM
eurjchem-1645	207	3	c	c	X
eurjchem-1645	207	4	.	.	PUNCT
eurjchem-1645	207	5	1h	1h	NUM
eurjchem-1645	207	6	nmr	nmr	NOUN
eurjchem-1645	207	7	(	(	PUNCT
eurjchem-1645	207	8	400	400	NUM
eurjchem-1645	207	9	mhz	mhz	NOUN
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eurjchem-1645	207	12	,	,	PUNCT
eurjchem-1645	207	13	δ	δ	PROPN
eurjchem-1645	207	14	,	,	PUNCT
eurjchem-1645	207	15	ppm	ppm	NOUN
eurjchem-1645	207	16	):	):	PUNCT
eurjchem-1645	207	17	1.39	1.39	NUM
eurjchem-1645	207	18	(	(	PUNCT
eurjchem-1645	207	19	s	s	PROPN
eurjchem-1645	207	20	,	,	PUNCT
eurjchem-1645	207	21	9h	9h	NUM
eurjchem-1645	207	22	,	,	PUNCT
eurjchem-1645	207	23	t‐bu	t‐bu	NOUN
eurjchem-1645	207	24	)	)	PUNCT
eurjchem-1645	207	25	,	,	PUNCT
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eurjchem-1645	207	27	(	(	PUNCT
eurjchem-1645	207	28	d	d	NOUN
eurjchem-1645	207	29	,	,	PUNCT
eurjchem-1645	207	30	2h	2h	NUM
eurjchem-1645	207	31	,	,	PUNCT
eurjchem-1645	207	32	j	j	PROPN
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eurjchem-1645	207	34	6.4	6.4	NUM
eurjchem-1645	207	35	hz	hz	NOUN
eurjchem-1645	207	36	,	,	PUNCT
eurjchem-1645	207	37	ch2	ch2	PROPN
eurjchem-1645	207	38	)	)	PUNCT
eurjchem-1645	207	39	,	,	PUNCT
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eurjchem-1645	207	41	(	(	PUNCT
eurjchem-1645	207	42	m	m	PROPN
eurjchem-1645	207	43	,	,	PUNCT
eurjchem-1645	207	44	2h	2h	NUM
eurjchem-1645	207	45	,	,	PUNCT
eurjchem-1645	207	46	ch2	ch2	PROPN
eurjchem-1645	207	47	)	)	PUNCT
eurjchem-1645	207	48	,	,	PUNCT
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eurjchem-1645	207	52	,	,	PUNCT
eurjchem-1645	207	53	2h	2h	NUM
eurjchem-1645	207	54	,	,	PUNCT
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eurjchem-1645	207	56	)	)	PUNCT
eurjchem-1645	207	57	,	,	PUNCT
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eurjchem-1645	207	62	1h	1h	NUM
eurjchem-1645	207	63	,	,	PUNCT
eurjchem-1645	207	64	ar‐h	ar‐h	NOUN
eurjchem-1645	207	65	)	)	PUNCT
eurjchem-1645	207	66	,	,	PUNCT
eurjchem-1645	207	67	7.38‐7.24	7.38‐7.24	NUM
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eurjchem-1645	207	69	m	m	PROPN
eurjchem-1645	207	70	,	,	PUNCT
eurjchem-1645	207	71	2h	2h	NUM
eurjchem-1645	207	72	,	,	PUNCT
eurjchem-1645	207	73	ar‐h	ar‐h	NOUN
eurjchem-1645	207	74	)	)	PUNCT
eurjchem-1645	207	75	,	,	PUNCT
eurjchem-1645	207	76	7.68‐7.81	7.68‐7.81	NUM
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eurjchem-1645	207	80	2h	2h	NUM
eurjchem-1645	207	81	,	,	PUNCT
eurjchem-1645	207	82	ar‐h	ar‐h	NOUN
eurjchem-1645	207	83	)	)	PUNCT
eurjchem-1645	207	84	.	.	PUNCT
eurjchem-1645	208	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	208	2	(	(	PUNCT
eurjchem-1645	208	3	ei	ei	X
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eurjchem-1645	208	7	z	z	PROPN
eurjchem-1645	208	8	):	):	PUNCT
eurjchem-1645	208	9	356	356	NUM
eurjchem-1645	208	10	(	(	PUNCT
eurjchem-1645	208	11	m+h	m+h	NOUN
eurjchem-1645	208	12	)	)	PUNCT
eurjchem-1645	208	13	.	.	PUNCT
eurjchem-1645	209	1	anal	anal	PROPN
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eurjchem-1645	209	4	.	.	PUNCT
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eurjchem-1645	210	2	c19h21n3o2s	c19h21n3o2s	PROPN
eurjchem-1645	210	3	:	:	PUNCT
eurjchem-1645	210	4	c	c	X
eurjchem-1645	210	5	,	,	PUNCT
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eurjchem-1645	210	8	h	h	NOUN
eurjchem-1645	210	9	,	,	PUNCT
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eurjchem-1645	210	12	n	n	CCONJ
eurjchem-1645	210	13	,	,	PUNCT
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eurjchem-1645	211	2	:	:	PUNCT
eurjchem-1645	212	1	c	c	X
eurjchem-1645	212	2	,	,	PUNCT
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eurjchem-1645	212	4	;	;	PUNCT
eurjchem-1645	213	1	h	h	NOUN
eurjchem-1645	213	2	,	,	PUNCT
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eurjchem-1645	213	4	;	;	PUNCT
eurjchem-1645	213	5	n	n	CCONJ
eurjchem-1645	213	6	,	,	PUNCT
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eurjchem-1645	213	9	.	.	PUNCT
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eurjchem-1645	214	6	(	(	PUNCT
eurjchem-1645	214	7	11c	11c	NUM
eurjchem-1645	214	8	):	):	PUNCT
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eurjchem-1645	214	10	:	:	PUNCT
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eurjchem-1645	214	12	.	.	PUNCT
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eurjchem-1645	215	2	:	:	PUNCT
eurjchem-1645	215	3	86	86	NUM
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eurjchem-1645	215	5	.	.	PUNCT
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eurjchem-1645	216	3	:	:	PUNCT
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eurjchem-1645	217	4	.	.	PUNCT
eurjchem-1645	218	1	1h	1h	NUM
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eurjchem-1645	218	3	(	(	PUNCT
eurjchem-1645	218	4	400	400	NUM
eurjchem-1645	218	5	mhz	mhz	NOUN
eurjchem-1645	218	6	,	,	PUNCT
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eurjchem-1645	218	8	,	,	PUNCT
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eurjchem-1645	218	10	,	,	PUNCT
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eurjchem-1645	218	12	):	):	PUNCT
eurjchem-1645	218	13	1.39	1.39	NUM
eurjchem-1645	218	14	(	(	PUNCT
eurjchem-1645	218	15	s	s	PROPN
eurjchem-1645	218	16	,	,	PUNCT
eurjchem-1645	218	17	9h	9h	NUM
eurjchem-1645	218	18	,	,	PUNCT
eurjchem-1645	218	19	t‐bu	t‐bu	NOUN
eurjchem-1645	218	20	)	)	PUNCT
eurjchem-1645	218	21	,	,	PUNCT
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eurjchem-1645	218	23	(	(	PUNCT
eurjchem-1645	218	24	2h	2h	NUM
eurjchem-1645	218	25	,	,	PUNCT
eurjchem-1645	218	26	d	d	NOUN
eurjchem-1645	218	27	,	,	PUNCT
eurjchem-1645	218	28	j	j	PROPN
eurjchem-1645	218	29	=	=	PROPN
eurjchem-1645	218	30	6.4	6.4	NUM
eurjchem-1645	218	31	hz	hz	NOUN
eurjchem-1645	218	32	,	,	PUNCT
eurjchem-1645	218	33	ch2	ch2	PROPN
eurjchem-1645	218	34	)	)	PUNCT
eurjchem-1645	218	35	,	,	PUNCT
eurjchem-1645	218	36	2.66	2.66	NUM
eurjchem-1645	218	37	(	(	PUNCT
eurjchem-1645	218	38	m	m	PROPN
eurjchem-1645	218	39	,	,	PUNCT
eurjchem-1645	218	40	2h	2h	NUM
eurjchem-1645	218	41	,	,	PUNCT
eurjchem-1645	218	42	ch2	ch2	PROPN
eurjchem-1645	218	43	)	)	PUNCT
eurjchem-1645	218	44	,	,	PUNCT
eurjchem-1645	218	45	3.61	3.61	NUM
eurjchem-1645	218	46	(	(	PUNCT
eurjchem-1645	218	47	s	s	PROPN
eurjchem-1645	218	48	,	,	PUNCT
eurjchem-1645	218	49	2h	2h	NUM
eurjchem-1645	218	50	,	,	PUNCT
eurjchem-1645	218	51	n‐ch2	n‐ch2	PROPN
eurjchem-1645	218	52	)	)	PUNCT
eurjchem-1645	218	53	,	,	PUNCT
eurjchem-1645	218	54	7.66‐7.45	7.66‐7.45	NUM
eurjchem-1645	218	55	(	(	PUNCT
eurjchem-1645	218	56	m	m	PROPN
eurjchem-1645	218	57	,	,	PUNCT
eurjchem-1645	218	58	3h	3h	NUM
eurjchem-1645	218	59	,	,	PUNCT
eurjchem-1645	218	60	ar‐h	ar‐h	NOUN
eurjchem-1645	218	61	)	)	PUNCT
eurjchem-1645	218	62	,	,	PUNCT
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eurjchem-1645	218	65	m	m	PROPN
eurjchem-1645	218	66	,	,	PUNCT
eurjchem-1645	218	67	2h	2h	NUM
eurjchem-1645	218	68	,	,	PUNCT
eurjchem-1645	218	69	ar‐h	ar‐h	NOUN
eurjchem-1645	218	70	)	)	PUNCT
eurjchem-1645	218	71	,	,	PUNCT
eurjchem-1645	218	72	8.78	8.78	NUM
eurjchem-1645	218	73	(	(	PUNCT
eurjchem-1645	218	74	s	s	PROPN
eurjchem-1645	218	75	,	,	PUNCT
eurjchem-1645	218	76	1h	1h	NUM
eurjchem-1645	218	77	,	,	PUNCT
eurjchem-1645	218	78	ar‐h	ar‐h	NOUN
eurjchem-1645	218	79	)	)	PUNCT
eurjchem-1645	218	80	.	.	PUNCT
eurjchem-1645	219	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	219	2	(	(	PUNCT
eurjchem-1645	219	3	ei	ei	X
eurjchem-1645	219	4	,	,	PUNCT
eurjchem-1645	219	5	m	m	PROPN
eurjchem-1645	219	6	/	/	SYM
eurjchem-1645	219	7	z	z	PROPN
eurjchem-1645	219	8	):	):	PUNCT
eurjchem-1645	219	9	351	351	NUM
eurjchem-1645	219	10	(	(	PUNCT
eurjchem-1645	219	11	m+h	m+h	PROPN
eurjchem-1645	219	12	)	)	PUNCT
eurjchem-1645	219	13	.	.	PUNCT
eurjchem-1645	220	1	anal	anal	PROPN
eurjchem-1645	220	2	.	.	PUNCT
eurjchem-1645	220	3	calcd	calcd	NOUN
eurjchem-1645	220	4	.	.	PUNCT
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eurjchem-1645	221	3	:	:	PUNCT
eurjchem-1645	221	4	c	c	X
eurjchem-1645	221	5	,	,	PUNCT
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eurjchem-1645	221	7	;	;	PUNCT
eurjchem-1645	221	8	h	h	X
eurjchem-1645	221	9	,	,	PUNCT
eurjchem-1645	221	10	6.33	6.33	NUM
eurjchem-1645	221	11	;	;	PUNCT
eurjchem-1645	221	12	n	n	CCONJ
eurjchem-1645	221	13	,	,	PUNCT
eurjchem-1645	221	14	15.99	15.99	NUM
eurjchem-1645	221	15	.	.	PUNCT
eurjchem-1645	221	16	found	find	VERB
eurjchem-1645	221	17	:	:	PUNCT
eurjchem-1645	222	1	c	c	X
eurjchem-1645	222	2	,	,	PUNCT
eurjchem-1645	222	3	68.56	68.56	NUM
eurjchem-1645	222	4	;	;	PUNCT
eurjchem-1645	222	5	h	h	NOUN
eurjchem-1645	222	6	,	,	PUNCT
eurjchem-1645	222	7	6.34	6.34	NUM
eurjchem-1645	222	8	;	;	PUNCT
eurjchem-1645	222	9	n	n	CCONJ
eurjchem-1645	222	10	,	,	PUNCT
eurjchem-1645	222	11	15.97	15.97	NUM
eurjchem-1645	222	12	%	%	NOUN
eurjchem-1645	222	13	.	.	PUNCT
eurjchem-1645	223	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	223	2	4,5,6,7‐tetrahydro‐3‐(quinolin‐5‐yl)pyrazolo[3	4,5,6,7‐tetrahydro‐3‐(quinolin‐5‐yl)pyrazolo[3	NOUN
eurjchem-1645	223	3	,	,	PUNCT
eurjchem-1645	223	4	4‐	4‐	PROPN
eurjchem-1645	223	5	c]pyridine‐1‐carboxylate	c]pyridine‐1‐carboxylate	PROPN
eurjchem-1645	223	6	(	(	PUNCT
eurjchem-1645	223	7	11d	11d	X
eurjchem-1645	223	8	):	):	PUNCT
eurjchem-1645	223	9	color	color	NOUN
eurjchem-1645	223	10	:	:	PUNCT
eurjchem-1645	223	11	yellow	yellow	ADJ
eurjchem-1645	223	12	.	.	PUNCT
eurjchem-1645	224	1	yield	yield	NOUN
eurjchem-1645	224	2	:	:	PUNCT
eurjchem-1645	224	3	84	84	NUM
eurjchem-1645	224	4	%	%	NOUN
eurjchem-1645	224	5	.	.	PUNCT
eurjchem-1645	225	1	m.p	m.p	PROPN
eurjchem-1645	225	2	.	.	PROPN
eurjchem-1645	225	3	:	:	PUNCT
eurjchem-1645	225	4	140‐141	140‐141	NUM
eurjchem-1645	225	5	°	°	SYM
eurjchem-1645	225	6	c	c	NOUN
eurjchem-1645	225	7	.	.	PUNCT
eurjchem-1645	226	1	1h	1h	NUM
eurjchem-1645	226	2	nmr	nmr	NOUN
eurjchem-1645	226	3	(	(	PUNCT
eurjchem-1645	226	4	400	400	NUM
eurjchem-1645	226	5	mhz	mhz	NOUN
eurjchem-1645	226	6	,	,	PUNCT
eurjchem-1645	226	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	226	8	,	,	PUNCT
eurjchem-1645	226	9	δ	δ	PROPN
eurjchem-1645	226	10	,	,	PUNCT
eurjchem-1645	226	11	ppm	ppm	NOUN
eurjchem-1645	226	12	):	):	PUNCT
eurjchem-1645	226	13	1.39	1.39	NUM
eurjchem-1645	226	14	(	(	PUNCT
eurjchem-1645	226	15	s	s	PROPN
eurjchem-1645	226	16	,	,	PUNCT
eurjchem-1645	226	17	9h	9h	NUM
eurjchem-1645	226	18	,	,	PUNCT
eurjchem-1645	226	19	t‐bu	t‐bu	NOUN
eurjchem-1645	226	20	)	)	PUNCT
eurjchem-1645	226	21	,	,	PUNCT
eurjchem-1645	226	22	2.33	2.33	NUM
eurjchem-1645	226	23	(	(	PUNCT
eurjchem-1645	226	24	d	d	NOUN
eurjchem-1645	226	25	,	,	PUNCT
eurjchem-1645	226	26	2h	2h	NUM
eurjchem-1645	226	27	,	,	PUNCT
eurjchem-1645	226	28	j	j	PROPN
eurjchem-1645	226	29	=	=	PROPN
eurjchem-1645	226	30	6.4	6.4	NUM
eurjchem-1645	226	31	hz	hz	NOUN
eurjchem-1645	226	32	,	,	PUNCT
eurjchem-1645	226	33	ch2	ch2	PROPN
eurjchem-1645	226	34	)	)	PUNCT
eurjchem-1645	226	35	,	,	PUNCT
eurjchem-1645	226	36	2.68	2.68	NUM
eurjchem-1645	226	37	(	(	PUNCT
eurjchem-1645	226	38	m	m	PROPN
eurjchem-1645	226	39	,	,	PUNCT
eurjchem-1645	226	40	2h	2h	NUM
eurjchem-1645	226	41	,	,	PUNCT
eurjchem-1645	226	42	ch2	ch2	PROPN
eurjchem-1645	226	43	)	)	PUNCT
eurjchem-1645	226	44	,	,	PUNCT
eurjchem-1645	226	45	3.61	3.61	NUM
eurjchem-1645	226	46	(	(	PUNCT
eurjchem-1645	226	47	s	s	PROPN
eurjchem-1645	226	48	,	,	PUNCT
eurjchem-1645	226	49	2h	2h	NUM
eurjchem-1645	226	50	,	,	PUNCT
eurjchem-1645	226	51	n‐ch2	n‐ch2	PROPN
eurjchem-1645	226	52	)	)	PUNCT
eurjchem-1645	226	53	,	,	PUNCT
eurjchem-1645	226	54	7.66‐7.45	7.66‐7.45	NUM
eurjchem-1645	226	55	(	(	PUNCT
eurjchem-1645	226	56	m	m	PROPN
eurjchem-1645	226	57	,	,	PUNCT
eurjchem-1645	226	58	3h	3h	NUM
eurjchem-1645	226	59	,	,	PUNCT
eurjchem-1645	226	60	ar‐h	ar‐h	NOUN
eurjchem-1645	226	61	)	)	PUNCT
eurjchem-1645	226	62	,	,	PUNCT
eurjchem-1645	226	63	8.19‐8.02	8.19‐8.02	PROPN
eurjchem-1645	226	64	(	(	PUNCT
eurjchem-1645	226	65	m	m	PROPN
eurjchem-1645	226	66	,	,	PUNCT
eurjchem-1645	226	67	2h	2h	NUM
eurjchem-1645	226	68	,	,	PUNCT
eurjchem-1645	226	69	ar‐h	ar‐h	NOUN
eurjchem-1645	226	70	)	)	PUNCT
eurjchem-1645	226	71	,	,	PUNCT
eurjchem-1645	226	72	8.78	8.78	NUM
eurjchem-1645	226	73	(	(	PUNCT
eurjchem-1645	226	74	s	s	PROPN
eurjchem-1645	226	75	,	,	PUNCT
eurjchem-1645	226	76	1h	1h	NUM
eurjchem-1645	226	77	,	,	PUNCT
eurjchem-1645	226	78	ar‐h	ar‐h	NOUN
eurjchem-1645	226	79	)	)	PUNCT
eurjchem-1645	226	80	.	.	PUNCT
eurjchem-1645	227	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	227	2	(	(	PUNCT
eurjchem-1645	227	3	ei	ei	X
eurjchem-1645	227	4	,	,	PUNCT
eurjchem-1645	227	5	m	m	PROPN
eurjchem-1645	227	6	/	/	SYM
eurjchem-1645	227	7	z	z	PROPN
eurjchem-1645	227	8	):	):	PUNCT
eurjchem-1645	227	9	351	351	NUM
eurjchem-1645	227	10	(	(	PUNCT
eurjchem-1645	227	11	m+h	m+h	PROPN
eurjchem-1645	227	12	)	)	PUNCT
eurjchem-1645	227	13	.	.	PUNCT
eurjchem-1645	228	1	anal	anal	PROPN
eurjchem-1645	228	2	.	.	PUNCT
eurjchem-1645	228	3	calcd	calcd	NOUN
eurjchem-1645	228	4	.	.	PUNCT
eurjchem-1645	229	1	for	for	SCONJ
eurjchem-1645	229	2	c20h22n4o2	c20h22n4o2	PROPN
eurjchem-1645	229	3	:	:	PUNCT
eurjchem-1645	229	4	c	c	X
eurjchem-1645	229	5	,	,	PUNCT
eurjchem-1645	229	6	68.55	68.55	NUM
eurjchem-1645	229	7	;	;	PUNCT
eurjchem-1645	229	8	h	h	X
eurjchem-1645	229	9	,	,	PUNCT
eurjchem-1645	229	10	6.33	6.33	NUM
eurjchem-1645	229	11	;	;	PUNCT
eurjchem-1645	229	12	n	n	CCONJ
eurjchem-1645	229	13	,	,	PUNCT
eurjchem-1645	229	14	15.99	15.99	NUM
eurjchem-1645	229	15	.	.	PUNCT
eurjchem-1645	229	16	found	find	VERB
eurjchem-1645	229	17	:	:	PUNCT
eurjchem-1645	230	1	c	c	X
eurjchem-1645	230	2	,	,	PUNCT
eurjchem-1645	230	3	68.57	68.57	NUM
eurjchem-1645	230	4	;	;	PUNCT
eurjchem-1645	230	5	h	h	NOUN
eurjchem-1645	230	6	,	,	PUNCT
eurjchem-1645	230	7	6.32	6.32	NUM
eurjchem-1645	230	8	;	;	PUNCT
eurjchem-1645	230	9	n	n	CCONJ
eurjchem-1645	230	10	,	,	PUNCT
eurjchem-1645	230	11	15.98	15.98	NUM
eurjchem-1645	230	12	%	%	NOUN
eurjchem-1645	230	13	.	.	PUNCT
eurjchem-1645	231	1	2.2.11	2.2.11	X
eurjchem-1645	231	2	.	.	PUNCT
eurjchem-1645	231	3	general	general	ADJ
eurjchem-1645	231	4	procedure	procedure	NOUN
eurjchem-1645	231	5	for	for	ADP
eurjchem-1645	231	6	synthesis	synthesis	NOUN
eurjchem-1645	231	7	of	of	ADP
eurjchem-1645	231	8	compounds	compound	NOUN
eurjchem-1645	231	9	(	(	PUNCT
eurjchem-1645	231	10	12a‐	12a‐	NUM
eurjchem-1645	231	11	h	h	NOUN
eurjchem-1645	231	12	)	)	PUNCT
eurjchem-1645	231	13	,	,	PUNCT
eurjchem-1645	231	14	step	step	NOUN
eurjchem-1645	231	15	(	(	PUNCT
eurjchem-1645	231	16	k	k	NOUN
eurjchem-1645	231	17	)	)	PUNCT
eurjchem-1645	231	18	to	to	ADP
eurjchem-1645	231	19	a	a	DET
eurjchem-1645	231	20	stirred	stir	VERB
eurjchem-1645	231	21	solution	solution	NOUN
eurjchem-1645	231	22	of	of	ADP
eurjchem-1645	231	23	compounds	compound	NOUN
eurjchem-1645	231	24	11a‐d	11a‐d	INTJ
eurjchem-1645	231	25	(	(	PUNCT
eurjchem-1645	231	26	1	1	NUM
eurjchem-1645	231	27	mmol	mmol	NOUN
eurjchem-1645	231	28	)	)	PUNCT
eurjchem-1645	231	29	was	be	AUX
eurjchem-1645	231	30	dissolved	dissolve	VERB
eurjchem-1645	231	31	in	in	ADP
eurjchem-1645	231	32	thf	thf	NOUN
eurjchem-1645	231	33	(	(	PUNCT
eurjchem-1645	231	34	10	10	NUM
eurjchem-1645	231	35	ml	ml	NOUN
eurjchem-1645	231	36	)	)	PUNCT
eurjchem-1645	231	37	.	.	PUNCT
eurjchem-1645	232	1	then	then	ADV
eurjchem-1645	232	2	,	,	PUNCT
eurjchem-1645	232	3	added	add	VERB
eurjchem-1645	232	4	2,6‐lutidine	2,6‐lutidine	NUM
eurjchem-1645	232	5	(	(	PUNCT
eurjchem-1645	232	6	2	2	NUM
eurjchem-1645	232	7	equiv	equiv	NOUN
eurjchem-1645	232	8	.	.	PUNCT
eurjchem-1645	232	9	)	)	PUNCT
eurjchem-1645	232	10	,	,	PUNCT
eurjchem-1645	232	11	dmap	dmap	NOUN
eurjchem-1645	232	12	(	(	PUNCT
eurjchem-1645	232	13	0.2	0.2	NUM
eurjchem-1645	232	14	equiv	equiv	NOUN
eurjchem-1645	232	15	.	.	PUNCT
eurjchem-1645	232	16	)	)	PUNCT
eurjchem-1645	233	1	and	and	CCONJ
eurjchem-1645	233	2	benzyl	benzyl	NOUN
eurjchem-1645	233	3	bromide	bromide	NOUN
eurjchem-1645	233	4	(	(	PUNCT
eurjchem-1645	233	5	1.2	1.2	NUM
eurjchem-1645	233	6	equiv	equiv	NOUN
eurjchem-1645	233	7	.	.	PUNCT
eurjchem-1645	233	8	)	)	PUNCT
eurjchem-1645	234	1	and	and	CCONJ
eurjchem-1645	234	2	stirred	stir	VERB
eurjchem-1645	234	3	reaction	reaction	NOUN
eurjchem-1645	234	4	mixture	mixture	NOUN
eurjchem-1645	234	5	to	to	PART
eurjchem-1645	234	6	room	room	VERB
eurjchem-1645	234	7	temperature	temperature	NOUN
eurjchem-1645	234	8	for	for	ADP
eurjchem-1645	234	9	8	8	NUM
eurjchem-1645	234	10	h.	h.	NOUN
eurjchem-1645	234	11	progress	progress	NOUN
eurjchem-1645	234	12	of	of	ADP
eurjchem-1645	234	13	reaction	reaction	NOUN
eurjchem-1645	234	14	was	be	AUX
eurjchem-1645	234	15	monitored	monitor	VERB
eurjchem-1645	234	16	by	by	ADP
eurjchem-1645	234	17	lc‐ms	lc‐ms	PRON
eurjchem-1645	234	18	for	for	ADP
eurjchem-1645	234	19	the	the	DET
eurjchem-1645	234	20	consumption	consumption	NOUN
eurjchem-1645	234	21	of	of	ADP
eurjchem-1645	234	22	starting	start	VERB
eurjchem-1645	234	23	material	material	NOUN
eurjchem-1645	234	24	.	.	PUNCT
eurjchem-1645	235	1	after	after	ADP
eurjchem-1645	235	2	completion	completion	NOUN
eurjchem-1645	235	3	the	the	DET
eurjchem-1645	235	4	reaction	reaction	NOUN
eurjchem-1645	235	5	the	the	DET
eurjchem-1645	235	6	reaction	reaction	NOUN
eurjchem-1645	235	7	mixture	mixture	NOUN
eurjchem-1645	235	8	evaporated	evaporate	VERB
eurjchem-1645	235	9	under	under	ADP
eurjchem-1645	235	10	reduced	reduced	ADJ
eurjchem-1645	235	11	pressure	pressure	NOUN
eurjchem-1645	235	12	to	to	PART
eurjchem-1645	235	13	obtain	obtain	VERB
eurjchem-1645	235	14	yellow	yellow	ADJ
eurjchem-1645	235	15	gummy	gummy	ADJ
eurjchem-1645	235	16	material	material	NOUN
eurjchem-1645	235	17	.	.	PUNCT
eurjchem-1645	236	1	the	the	DET
eurjchem-1645	236	2	obtained	obtain	VERB
eurjchem-1645	236	3	crude	crude	NOUN
eurjchem-1645	236	4	was	be	AUX
eurjchem-1645	236	5	washed	wash	VERB
eurjchem-1645	236	6	with	with	ADP
eurjchem-1645	236	7	20	20	NUM
eurjchem-1645	236	8	%	%	NOUN
eurjchem-1645	236	9	ethyl	ethyl	PROPN
eurjchem-1645	236	10	acetate	acetate	NOUN
eurjchem-1645	236	11	:	:	PUNCT
eurjchem-1645	236	12	hexane	hexane	NOUN
eurjchem-1645	236	13	(	(	PUNCT
eurjchem-1645	236	14	v	v	NOUN
eurjchem-1645	236	15	:	:	PUNCT
eurjchem-1645	236	16	v	v	NOUN
eurjchem-1645	236	17	,	,	PUNCT
eurjchem-1645	236	18	20:80	20:80	NUM
eurjchem-1645	236	19	)	)	PUNCT
eurjchem-1645	236	20	,	,	PUNCT
eurjchem-1645	236	21	hexane	hexane	NOUN
eurjchem-1645	236	22	and	and	CCONJ
eurjchem-1645	236	23	diethyl	diethyl	NOUN
eurjchem-1645	236	24	ether	ether	NOUN
eurjchem-1645	236	25	to	to	ADP
eurjchem-1645	236	26	404	404	NUM
eurjchem-1645	236	27	pawar	pawar	NOUN
eurjchem-1645	236	28	et	et	PROPN
eurjchem-1645	236	29	al	al	PROPN
eurjchem-1645	236	30	.	.	PUNCT
eurjchem-1645	236	31	/	/	SYM
eurjchem-1645	236	32	european	european	PROPN
eurjchem-1645	236	33	journal	journal	PROPN
eurjchem-1645	236	34	of	of	ADP
eurjchem-1645	236	35	chemistry	chemistry	NOUN
eurjchem-1645	236	36	8	8	NUM
eurjchem-1645	236	37	(	(	PUNCT
eurjchem-1645	236	38	4	4	NUM
eurjchem-1645	236	39	)	)	PUNCT
eurjchem-1645	236	40	(	(	PUNCT
eurjchem-1645	236	41	2017	2017	NUM
eurjchem-1645	236	42	)	)	PUNCT
eurjchem-1645	236	43	400‐409	400‐409	NUM
eurjchem-1645	236	44	obtain	obtain	VERB
eurjchem-1645	236	45	yellow	yellow	ADJ
eurjchem-1645	236	46	semisolid	semisolid	NOUN
eurjchem-1645	236	47	compound	compound	NOUN
eurjchem-1645	236	48	.	.	PUNCT
eurjchem-1645	237	1	crystallization	crystallization	NOUN
eurjchem-1645	237	2	of	of	ADP
eurjchem-1645	237	3	crude	crude	NOUN
eurjchem-1645	237	4	was	be	AUX
eurjchem-1645	237	5	done	do	VERB
eurjchem-1645	237	6	by	by	ADP
eurjchem-1645	237	7	using	use	VERB
eurjchem-1645	237	8	pentane	pentane	NOUN
eurjchem-1645	237	9	and	and	CCONJ
eurjchem-1645	237	10	diethyl	diethyl	NOUN
eurjchem-1645	237	11	ether	ether	NOUN
eurjchem-1645	237	12	to	to	PART
eurjchem-1645	237	13	obtain	obtain	VERB
eurjchem-1645	237	14	solid	solid	ADJ
eurjchem-1645	237	15	compounds	compound	NOUN
eurjchem-1645	237	16	12a‐h	12a‐h	NOUN
eurjchem-1645	237	17	.	.	PUNCT
eurjchem-1645	238	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	238	2	3‐(benzofuran‐2‐yl)‐4,5	3‐(benzofuran‐2‐yl)‐4,5	NUM
eurjchem-1645	238	3	,	,	PUNCT
eurjchem-1645	238	4	6	6	NUM
eurjchem-1645	238	5	,	,	PUNCT
eurjchem-1645	238	6	7‐tetrahydro‐6‐(3‐met	7‐tetrahydro‐6‐(3‐met	NUM
eurjchem-1645	238	7	hoxyphenyl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	hoxyphenyl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	238	8	(	(	PUNCT
eurjchem-1645	238	9	12a	12a	NUM
eurjchem-1645	238	10	):	):	PUNCT
eurjchem-1645	238	11	color	color	NOUN
eurjchem-1645	238	12	:	:	PUNCT
eurjchem-1645	238	13	yellow	yellow	ADJ
eurjchem-1645	238	14	.	.	PUNCT
eurjchem-1645	239	1	yield	yield	NOUN
eurjchem-1645	239	2	:	:	PUNCT
eurjchem-1645	239	3	85	85	NUM
eurjchem-1645	239	4	%	%	NOUN
eurjchem-1645	239	5	.	.	PUNCT
eurjchem-1645	240	1	m.p	m.p	PROPN
eurjchem-1645	240	2	.	.	PROPN
eurjchem-1645	240	3	:	:	PUNCT
eurjchem-1645	241	1	134‐135	134‐135	PROPN
eurjchem-1645	241	2	°	°	SYM
eurjchem-1645	241	3	c	c	PROPN
eurjchem-1645	241	4	.	.	PUNCT
eurjchem-1645	241	5	1h	1h	NUM
eurjchem-1645	241	6	nmr	nmr	NOUN
eurjchem-1645	241	7	(	(	PUNCT
eurjchem-1645	241	8	400	400	NUM
eurjchem-1645	241	9	mhz	mhz	NOUN
eurjchem-1645	241	10	,	,	PUNCT
eurjchem-1645	241	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	241	12	,	,	PUNCT
eurjchem-1645	241	13	δ	δ	PROPN
eurjchem-1645	241	14	,	,	PUNCT
eurjchem-1645	241	15	ppm	ppm	NUM
eurjchem-1645	241	16	):	):	PUNCT
eurjchem-1645	241	17	1.38	1.38	NUM
eurjchem-1645	241	18	(	(	PUNCT
eurjchem-1645	241	19	s	s	PROPN
eurjchem-1645	241	20	,	,	PUNCT
eurjchem-1645	241	21	9h	9h	NUM
eurjchem-1645	241	22	,	,	PUNCT
eurjchem-1645	241	23	t‐bu	t‐bu	NOUN
eurjchem-1645	241	24	)	)	PUNCT
eurjchem-1645	241	25	,	,	PUNCT
eurjchem-1645	241	26	2.84	2.84	NUM
eurjchem-1645	241	27	(	(	PUNCT
eurjchem-1645	241	28	d	d	PROPN
eurjchem-1645	241	29	,	,	PUNCT
eurjchem-1645	241	30	2h	2h	NUM
eurjchem-1645	241	31	,	,	PUNCT
eurjchem-1645	241	32	j	j	PROPN
eurjchem-1645	241	33	=	=	SYM
eurjchem-1645	241	34	8hz	8hz	NOUN
eurjchem-1645	241	35	,	,	PUNCT
eurjchem-1645	241	36	ch2	ch2	PROPN
eurjchem-1645	241	37	)	)	PUNCT
eurjchem-1645	241	38	,	,	PUNCT
eurjchem-1645	241	39	3.62	3.62	NUM
eurjchem-1645	241	40	(	(	PUNCT
eurjchem-1645	241	41	s	s	PROPN
eurjchem-1645	241	42	,	,	PUNCT
eurjchem-1645	241	43	2h	2h	NUM
eurjchem-1645	241	44	,	,	PUNCT
eurjchem-1645	241	45	ch2	ch2	PROPN
eurjchem-1645	241	46	)	)	PUNCT
eurjchem-1645	241	47	,	,	PUNCT
eurjchem-1645	241	48	3.78	3.78	NUM
eurjchem-1645	241	49	(	(	PUNCT
eurjchem-1645	241	50	s	s	PROPN
eurjchem-1645	241	51	,	,	PUNCT
eurjchem-1645	241	52	3h	3h	NUM
eurjchem-1645	241	53	,	,	PUNCT
eurjchem-1645	241	54	o‐ch3	o‐ch3	PROPN
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eurjchem-1645	241	56	,	,	PUNCT
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eurjchem-1645	241	59	d	d	PROPN
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eurjchem-1645	241	61	2h	2h	NUM
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eurjchem-1645	241	69	ch2	ch2	PROPN
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eurjchem-1645	241	71	,	,	PUNCT
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eurjchem-1645	241	76	1h	1h	NUM
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eurjchem-1645	242	4	,	,	PUNCT
eurjchem-1645	242	5	ar‐h	ar‐h	NOUN
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eurjchem-1645	242	7	,	,	PUNCT
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eurjchem-1645	242	11	,	,	PUNCT
eurjchem-1645	242	12	2h	2h	NUM
eurjchem-1645	242	13	,	,	PUNCT
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eurjchem-1645	242	24	)	)	PUNCT
eurjchem-1645	242	25	,	,	PUNCT
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eurjchem-1645	242	30	1h	1h	NUM
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eurjchem-1645	242	33	=	=	SYM
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eurjchem-1645	242	36	,	,	PUNCT
eurjchem-1645	242	37	ar‐h	ar‐h	NOUN
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eurjchem-1645	242	39	,	,	PUNCT
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eurjchem-1645	242	44	2h	2h	NUM
eurjchem-1645	242	45	,	,	PUNCT
eurjchem-1645	242	46	ar‐h	ar‐h	NOUN
eurjchem-1645	242	47	)	)	PUNCT
eurjchem-1645	242	48	.	.	PUNCT
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eurjchem-1645	243	8	):	):	PUNCT
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eurjchem-1645	243	11	m+h	m+h	NOUN
eurjchem-1645	243	12	)	)	PUNCT
eurjchem-1645	243	13	.	.	PUNCT
eurjchem-1645	244	1	anal	anal	PROPN
eurjchem-1645	244	2	.	.	PUNCT
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eurjchem-1645	244	4	.	.	PUNCT
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eurjchem-1645	245	2	c26h27n3o4	c26h27n3o4	NOUN
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eurjchem-1645	245	4	c	c	X
eurjchem-1645	245	5	,	,	PUNCT
eurjchem-1645	245	6	70.09	70.09	NUM
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eurjchem-1645	245	8	h	h	NOUN
eurjchem-1645	245	9	,	,	PUNCT
eurjchem-1645	245	10	6.11	6.11	NUM
eurjchem-1645	245	11	;	;	PUNCT
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eurjchem-1645	245	13	,	,	PUNCT
eurjchem-1645	245	14	9.43	9.43	NUM
eurjchem-1645	245	15	.	.	PUNCT
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eurjchem-1645	245	17	:	:	PUNCT
eurjchem-1645	246	1	c	c	X
eurjchem-1645	246	2	,	,	PUNCT
eurjchem-1645	246	3	70.07	70.07	NUM
eurjchem-1645	246	4	;	;	PUNCT
eurjchem-1645	246	5	h	h	NOUN
eurjchem-1645	246	6	,	,	PUNCT
eurjchem-1645	246	7	6.12	6.12	NUM
eurjchem-1645	246	8	;	;	PUNCT
eurjchem-1645	246	9	n	n	CCONJ
eurjchem-1645	246	10	,	,	PUNCT
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eurjchem-1645	246	12	%	%	NOUN
eurjchem-1645	246	13	.	.	PUNCT
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eurjchem-1645	247	3	,	,	PUNCT
eurjchem-1645	247	4	5	5	NUM
eurjchem-1645	247	5	,	,	PUNCT
eurjchem-1645	247	6	6	6	NUM
eurjchem-1645	247	7	,	,	PUNCT
eurjchem-1645	247	8	7‐tetrahydro‐6‐	7‐tetrahydro‐6‐	PROPN
eurjchem-1645	247	9	(	(	PUNCT
eurjchem-1645	247	10	3‐methoxyphenyl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	3‐methoxyphenyl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NUM
eurjchem-1645	247	11	(	(	PUNCT
eurjchem-1645	247	12	12b	12b	NOUN
eurjchem-1645	247	13	):	):	PUNCT
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eurjchem-1645	247	15	:	:	PUNCT
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eurjchem-1645	247	17	.	.	PUNCT
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eurjchem-1645	248	2	:	:	PUNCT
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eurjchem-1645	248	5	.	.	PUNCT
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eurjchem-1645	249	2	.	.	PROPN
eurjchem-1645	249	3	:	:	PUNCT
eurjchem-1645	250	1	144‐145	144‐145	NUM
eurjchem-1645	250	2	°	°	SYM
eurjchem-1645	250	3	c	c	PROPN
eurjchem-1645	250	4	.	.	PUNCT
eurjchem-1645	250	5	1h	1h	NUM
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eurjchem-1645	250	7	(	(	PUNCT
eurjchem-1645	250	8	400	400	NUM
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eurjchem-1645	250	10	,	,	PUNCT
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eurjchem-1645	250	12	,	,	PUNCT
eurjchem-1645	250	13	δ	δ	PROPN
eurjchem-1645	250	14	,	,	PUNCT
eurjchem-1645	250	15	ppm	ppm	NUM
eurjchem-1645	250	16	):	):	PUNCT
eurjchem-1645	250	17	1.38	1.38	NUM
eurjchem-1645	250	18	(	(	PUNCT
eurjchem-1645	250	19	s	s	PROPN
eurjchem-1645	250	20	,	,	PUNCT
eurjchem-1645	250	21	9h	9h	NUM
eurjchem-1645	250	22	,	,	PUNCT
eurjchem-1645	250	23	t‐bu	t‐bu	NOUN
eurjchem-1645	250	24	)	)	PUNCT
eurjchem-1645	250	25	,	,	PUNCT
eurjchem-1645	250	26	2.97‐2.81	2.97‐2.81	NUM
eurjchem-1645	250	27	(	(	PUNCT
eurjchem-1645	250	28	m	m	PROPN
eurjchem-1645	250	29	,	,	PUNCT
eurjchem-1645	250	30	2h	2h	NUM
eurjchem-1645	250	31	,	,	PUNCT
eurjchem-1645	250	32	ch2	ch2	PROPN
eurjchem-1645	250	33	)	)	PUNCT
eurjchem-1645	250	34	,	,	PUNCT
eurjchem-1645	250	35	3.63	3.63	NUM
eurjchem-1645	250	36	(	(	PUNCT
eurjchem-1645	250	37	s	s	PROPN
eurjchem-1645	250	38	,	,	PUNCT
eurjchem-1645	250	39	2h	2h	NUM
eurjchem-1645	250	40	,	,	PUNCT
eurjchem-1645	250	41	ch2	ch2	PROPN
eurjchem-1645	250	42	)	)	PUNCT
eurjchem-1645	250	43	,	,	PUNCT
eurjchem-1645	250	44	3.76	3.76	NUM
eurjchem-1645	250	45	(	(	PUNCT
eurjchem-1645	250	46	s	s	PROPN
eurjchem-1645	250	47	,	,	PUNCT
eurjchem-1645	250	48	3h	3h	NUM
eurjchem-1645	250	49	,	,	PUNCT
eurjchem-1645	250	50	o‐ch3	o‐ch3	PROPN
eurjchem-1645	250	51	)	)	PUNCT
eurjchem-1645	250	52	,	,	PUNCT
eurjchem-1645	250	53	4.36	4.36	NUM
eurjchem-1645	250	54	(	(	PUNCT
eurjchem-1645	250	55	d	d	PROPN
eurjchem-1645	250	56	,	,	PUNCT
eurjchem-1645	250	57	2h	2h	NUM
eurjchem-1645	250	58	,	,	PUNCT
eurjchem-1645	250	59	j	j	PROPN
eurjchem-1645	250	60	=	=	PROPN
eurjchem-1645	250	61	8.4	8.4	NUM
eurjchem-1645	250	62	hz	hz	NOUN
eurjchem-1645	250	63	,	,	PUNCT
eurjchem-1645	250	64	n‐ch2	n‐ch2	PROPN
eurjchem-1645	250	65	)	)	PUNCT
eurjchem-1645	250	66	,	,	PUNCT
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eurjchem-1645	250	68	(	(	PUNCT
eurjchem-1645	250	69	t	t	PROPN
eurjchem-1645	250	70	,	,	PUNCT
eurjchem-1645	250	71	1h	1h	NUM
eurjchem-1645	250	72	,	,	PUNCT
eurjchem-1645	250	73	j	j	PROPN
eurjchem-1645	250	74	=	=	SYM
eurjchem-1645	250	75	7.6	7.6	NUM
eurjchem-1645	250	76	hz	hz	NOUN
eurjchem-1645	250	77	,	,	PUNCT
eurjchem-1645	250	78	ar‐h	ar‐h	PROPN
eurjchem-1645	250	79	)	)	PUNCT
eurjchem-1645	250	80	,	,	PUNCT
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eurjchem-1645	250	82	(	(	PUNCT
eurjchem-1645	250	83	s	s	PROPN
eurjchem-1645	250	84	,	,	PUNCT
eurjchem-1645	250	85	1h	1h	NUM
eurjchem-1645	250	86	,	,	PUNCT
eurjchem-1645	250	87	ar‐h	ar‐h	NOUN
eurjchem-1645	250	88	)	)	PUNCT
eurjchem-1645	250	89	,	,	PUNCT
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eurjchem-1645	250	91	(	(	PUNCT
eurjchem-1645	250	92	m	m	PROPN
eurjchem-1645	250	93	,	,	PUNCT
eurjchem-1645	250	94	1h	1h	NUM
eurjchem-1645	250	95	,	,	PUNCT
eurjchem-1645	250	96	ar‐h	ar‐h	NOUN
eurjchem-1645	250	97	)	)	PUNCT
eurjchem-1645	250	98	,	,	PUNCT
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eurjchem-1645	250	102	,	,	PUNCT
eurjchem-1645	250	103	2h	2h	NUM
eurjchem-1645	250	104	,	,	PUNCT
eurjchem-1645	250	105	ar‐h	ar‐h	NOUN
eurjchem-1645	250	106	)	)	PUNCT
eurjchem-1645	250	107	,	,	PUNCT
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eurjchem-1645	250	109	(	(	PUNCT
eurjchem-1645	250	110	m	m	PROPN
eurjchem-1645	250	111	,	,	PUNCT
eurjchem-1645	250	112	2h	2h	NUM
eurjchem-1645	250	113	,	,	PUNCT
eurjchem-1645	250	114	ar‐h	ar‐h	NOUN
eurjchem-1645	250	115	)	)	PUNCT
eurjchem-1645	250	116	,	,	PUNCT
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eurjchem-1645	250	118	(	(	PUNCT
eurjchem-1645	250	119	m	m	PROPN
eurjchem-1645	250	120	,	,	PUNCT
eurjchem-1645	250	121	2h	2h	NUM
eurjchem-1645	250	122	,	,	PUNCT
eurjchem-1645	250	123	ar‐h	ar‐h	NOUN
eurjchem-1645	250	124	)	)	PUNCT
eurjchem-1645	250	125	.	.	PUNCT
eurjchem-1645	251	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	251	2	(	(	PUNCT
eurjchem-1645	251	3	ei	ei	X
eurjchem-1645	251	4	,	,	PUNCT
eurjchem-1645	251	5	m	m	PROPN
eurjchem-1645	251	6	/	/	SYM
eurjchem-1645	251	7	z	z	NOUN
eurjchem-1645	251	8	):	):	PUNCT
eurjchem-1645	251	9	462	462	NUM
eurjchem-1645	251	10	(	(	PUNCT
eurjchem-1645	251	11	m+h	m+h	PROPN
eurjchem-1645	251	12	)	)	PUNCT
eurjchem-1645	251	13	.	.	PUNCT
eurjchem-1645	252	1	anal	anal	PROPN
eurjchem-1645	252	2	.	.	PUNCT
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eurjchem-1645	252	4	.	.	PUNCT
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eurjchem-1645	253	3	:	:	PUNCT
eurjchem-1645	253	4	c	c	X
eurjchem-1645	253	5	,	,	PUNCT
eurjchem-1645	253	6	67.66	67.66	NUM
eurjchem-1645	253	7	;	;	PUNCT
eurjchem-1645	253	8	h	h	NOUN
eurjchem-1645	253	9	,	,	PUNCT
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eurjchem-1645	253	11	;	;	PUNCT
eurjchem-1645	253	12	n	n	CCONJ
eurjchem-1645	253	13	,	,	PUNCT
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eurjchem-1645	253	15	.	.	PUNCT
eurjchem-1645	253	16	found	find	VERB
eurjchem-1645	253	17	:	:	PUNCT
eurjchem-1645	254	1	c	c	X
eurjchem-1645	254	2	,	,	PUNCT
eurjchem-1645	254	3	67.63	67.63	NUM
eurjchem-1645	254	4	;	;	PUNCT
eurjchem-1645	254	5	h	h	NOUN
eurjchem-1645	254	6	,	,	PUNCT
eurjchem-1645	254	7	5.92	5.92	NUM
eurjchem-1645	254	8	;	;	PUNCT
eurjchem-1645	254	9	n	n	CCONJ
eurjchem-1645	254	10	,	,	PUNCT
eurjchem-1645	254	11	9.12	9.12	NUM
eurjchem-1645	254	12	%	%	NOUN
eurjchem-1645	254	13	.	.	PUNCT
eurjchem-1645	255	1	tert‐butyl	tert‐butyl	PUNCT
eurjchem-1645	255	2	4,5,6,7‐tetrahydro‐6‐(3‐methoxyphenyl)‐3‐(quino	4,5,6,7‐tetrahydro‐6‐(3‐methoxyphenyl)‐3‐(quino	PUNCT
eurjchem-1645	255	3	lin‐3‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	lin‐3‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	255	4	(	(	PUNCT
eurjchem-1645	255	5	12c	12c	NUM
eurjchem-1645	255	6	):	):	PUNCT
eurjchem-1645	255	7	color	color	NOUN
eurjchem-1645	255	8	:	:	PUNCT
eurjchem-1645	255	9	white	white	ADJ
eurjchem-1645	255	10	.	.	PUNCT
eurjchem-1645	255	11	yield	yield	NOUN
eurjchem-1645	255	12	:	:	PUNCT
eurjchem-1645	255	13	91	91	NUM
eurjchem-1645	255	14	%	%	NOUN
eurjchem-1645	255	15	.	.	PUNCT
eurjchem-1645	256	1	m.p	m.p	PROPN
eurjchem-1645	256	2	.	.	PROPN
eurjchem-1645	256	3	:	:	PUNCT
eurjchem-1645	257	1	147‐148	147‐148	NUM
eurjchem-1645	257	2	°	°	SYM
eurjchem-1645	257	3	c	c	PROPN
eurjchem-1645	257	4	.	.	PUNCT
eurjchem-1645	258	1	1h	1h	NUM
eurjchem-1645	258	2	nmr	nmr	NOUN
eurjchem-1645	258	3	(	(	PUNCT
eurjchem-1645	258	4	400	400	NUM
eurjchem-1645	258	5	mhz	mhz	NOUN
eurjchem-1645	258	6	,	,	PUNCT
eurjchem-1645	258	7	dmso‐	dmso‐	NUM
eurjchem-1645	258	8	d6	d6	NOUN
eurjchem-1645	258	9	,	,	PUNCT
eurjchem-1645	258	10	δ	δ	PROPN
eurjchem-1645	258	11	,	,	PUNCT
eurjchem-1645	258	12	ppm	ppm	NUM
eurjchem-1645	258	13	):	):	PUNCT
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eurjchem-1645	258	15	(	(	PUNCT
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eurjchem-1645	258	17	,	,	PUNCT
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eurjchem-1645	258	19	,	,	PUNCT
eurjchem-1645	258	20	t‐bu	t‐bu	NOUN
eurjchem-1645	258	21	)	)	PUNCT
eurjchem-1645	258	22	,	,	PUNCT
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eurjchem-1645	258	24	(	(	PUNCT
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eurjchem-1645	258	26	,	,	PUNCT
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eurjchem-1645	258	28	,	,	PUNCT
eurjchem-1645	258	29	j	j	PROPN
eurjchem-1645	258	30	=	=	PROPN
eurjchem-1645	258	31	8.2	8.2	NUM
eurjchem-1645	258	32	hz	hz	NOUN
eurjchem-1645	258	33	,	,	PUNCT
eurjchem-1645	258	34	ch2	ch2	PROPN
eurjchem-1645	258	35	)	)	PUNCT
eurjchem-1645	258	36	,	,	PUNCT
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eurjchem-1645	258	38	(	(	PUNCT
eurjchem-1645	258	39	t	t	PROPN
eurjchem-1645	258	40	,	,	PUNCT
eurjchem-1645	258	41	2h	2h	NUM
eurjchem-1645	258	42	,	,	PUNCT
eurjchem-1645	258	43	j	j	PROPN
eurjchem-1645	258	44	=	=	PROPN
eurjchem-1645	258	45	8.2	8.2	NUM
eurjchem-1645	258	46	hz	hz	NOUN
eurjchem-1645	258	47	,	,	PUNCT
eurjchem-1645	258	48	ch2	ch2	PROPN
eurjchem-1645	258	49	)	)	PUNCT
eurjchem-1645	258	50	,	,	PUNCT
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eurjchem-1645	258	54	,	,	PUNCT
eurjchem-1645	258	55	3h	3h	NUM
eurjchem-1645	258	56	,	,	PUNCT
eurjchem-1645	258	57	o‐ch3	o‐ch3	PROPN
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eurjchem-1645	258	59	,	,	PUNCT
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eurjchem-1645	258	67	)	)	PUNCT
eurjchem-1645	258	68	,	,	PUNCT
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eurjchem-1645	258	72	,	,	PUNCT
eurjchem-1645	258	73	1h	1h	NUM
eurjchem-1645	258	74	,	,	PUNCT
eurjchem-1645	258	75	ar‐h	ar‐h	NOUN
eurjchem-1645	258	76	)	)	PUNCT
eurjchem-1645	258	77	,	,	PUNCT
eurjchem-1645	258	78	6.56	6.56	NUM
eurjchem-1645	258	79	(	(	PUNCT
eurjchem-1645	258	80	s	s	PROPN
eurjchem-1645	258	81	,	,	PUNCT
eurjchem-1645	258	82	1h	1h	NUM
eurjchem-1645	258	83	,	,	PUNCT
eurjchem-1645	258	84	ar‐h	ar‐h	NOUN
eurjchem-1645	258	85	)	)	PUNCT
eurjchem-1645	258	86	,	,	PUNCT
eurjchem-1645	258	87	6.64	6.64	NUM
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eurjchem-1645	258	89	d	d	PROPN
eurjchem-1645	258	90	,	,	PUNCT
eurjchem-1645	258	91	1h	1h	NUM
eurjchem-1645	258	92	,	,	PUNCT
eurjchem-1645	258	93	j	j	PROPN
eurjchem-1645	258	94	=	=	SYM
eurjchem-1645	258	95	7.6	7.6	NUM
eurjchem-1645	258	96	hz	hz	NOUN
eurjchem-1645	258	97	,	,	PUNCT
eurjchem-1645	258	98	ar‐	ar‐	PROPN
eurjchem-1645	258	99	h	h	NOUN
eurjchem-1645	258	100	)	)	PUNCT
eurjchem-1645	258	101	,	,	PUNCT
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eurjchem-1645	258	104	t	t	PROPN
eurjchem-1645	258	105	,	,	PUNCT
eurjchem-1645	258	106	1h	1h	NUM
eurjchem-1645	258	107	,	,	PUNCT
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eurjchem-1645	258	109	=	=	SYM
eurjchem-1645	258	110	7.8	7.8	NUM
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eurjchem-1645	258	112	,	,	PUNCT
eurjchem-1645	258	113	ar‐h	ar‐h	NOUN
eurjchem-1645	258	114	)	)	PUNCT
eurjchem-1645	258	115	,	,	PUNCT
eurjchem-1645	258	116	7.81‐7.55	7.81‐7.55	NUM
eurjchem-1645	258	117	(	(	PUNCT
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eurjchem-1645	258	119	,	,	PUNCT
eurjchem-1645	258	120	2h	2h	NUM
eurjchem-1645	258	121	,	,	PUNCT
eurjchem-1645	258	122	j	j	PROPN
eurjchem-1645	258	123	=	=	PROPN
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eurjchem-1645	258	126	,	,	PUNCT
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eurjchem-1645	258	128	hz	hz	NOUN
eurjchem-1645	258	129	,	,	PUNCT
eurjchem-1645	258	130	ar‐h	ar‐h	PROPN
eurjchem-1645	258	131	)	)	PUNCT
eurjchem-1645	258	132	,	,	PUNCT
eurjchem-1645	258	133	8.08	8.08	NUM
eurjchem-1645	258	134	(	(	PUNCT
eurjchem-1645	258	135	t	t	PROPN
eurjchem-1645	258	136	,	,	PUNCT
eurjchem-1645	258	137	2h	2h	NUM
eurjchem-1645	258	138	,	,	PUNCT
eurjchem-1645	258	139	j	j	PROPN
eurjchem-1645	258	140	=	=	PROPN
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eurjchem-1645	258	146	,	,	PUNCT
eurjchem-1645	258	147	8.58	8.58	NUM
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eurjchem-1645	258	150	,	,	PUNCT
eurjchem-1645	258	151	1h	1h	NUM
eurjchem-1645	258	152	,	,	PUNCT
eurjchem-1645	258	153	ar‐h	ar‐h	NOUN
eurjchem-1645	258	154	)	)	PUNCT
eurjchem-1645	258	155	,	,	PUNCT
eurjchem-1645	258	156	9.38	9.38	NUM
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eurjchem-1645	258	158	s	s	PROPN
eurjchem-1645	258	159	,	,	PUNCT
eurjchem-1645	258	160	1h	1h	NUM
eurjchem-1645	258	161	,	,	PUNCT
eurjchem-1645	258	162	ar‐h	ar‐h	NOUN
eurjchem-1645	258	163	)	)	PUNCT
eurjchem-1645	258	164	,	,	PUNCT
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eurjchem-1645	258	169	1h	1h	NUM
eurjchem-1645	258	170	,	,	PUNCT
eurjchem-1645	258	171	ar‐h	ar‐h	NOUN
eurjchem-1645	258	172	)	)	PUNCT
eurjchem-1645	258	173	.	.	PUNCT
eurjchem-1645	259	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	259	2	(	(	PUNCT
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eurjchem-1645	259	8	):	):	PUNCT
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eurjchem-1645	259	11	m+h	m+h	NOUN
eurjchem-1645	259	12	)	)	PUNCT
eurjchem-1645	259	13	.	.	PUNCT
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eurjchem-1645	260	2	.	.	PUNCT
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eurjchem-1645	260	4	.	.	PUNCT
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eurjchem-1645	261	5	,	,	PUNCT
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eurjchem-1645	261	9	,	,	PUNCT
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eurjchem-1645	261	11	;	;	PUNCT
eurjchem-1645	261	12	n	n	CCONJ
eurjchem-1645	261	13	,	,	PUNCT
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eurjchem-1645	261	17	:	:	PUNCT
eurjchem-1645	262	1	c	c	X
eurjchem-1645	262	2	,	,	PUNCT
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eurjchem-1645	262	4	;	;	PUNCT
eurjchem-1645	263	1	h	h	NOUN
eurjchem-1645	263	2	,	,	PUNCT
eurjchem-1645	263	3	6.20	6.20	NUM
eurjchem-1645	263	4	;	;	PUNCT
eurjchem-1645	263	5	n	n	CCONJ
eurjchem-1645	263	6	,	,	PUNCT
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eurjchem-1645	264	4	(	(	PUNCT
eurjchem-1645	264	5	12d	12d	NUM
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eurjchem-1645	264	8	:	:	PUNCT
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eurjchem-1645	265	2	:	:	PUNCT
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eurjchem-1645	265	5	.	.	PUNCT
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eurjchem-1645	266	3	:	:	PUNCT
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eurjchem-1645	267	2	°	°	ADP
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eurjchem-1645	268	1	1h	1h	NUM
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eurjchem-1645	268	3	(	(	PUNCT
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eurjchem-1645	268	5	mhz	mhz	NOUN
eurjchem-1645	268	6	,	,	PUNCT
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eurjchem-1645	268	18	9h	9h	NUM
eurjchem-1645	268	19	,	,	PUNCT
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eurjchem-1645	268	21	)	)	PUNCT
eurjchem-1645	268	22	,	,	PUNCT
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eurjchem-1645	268	24	(	(	PUNCT
eurjchem-1645	268	25	s	s	PROPN
eurjchem-1645	268	26	,	,	PUNCT
eurjchem-1645	268	27	2h	2h	NUM
eurjchem-1645	268	28	,	,	PUNCT
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eurjchem-1645	268	30	)	)	PUNCT
eurjchem-1645	268	31	,	,	PUNCT
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eurjchem-1645	268	34	s	s	PROPN
eurjchem-1645	268	35	,	,	PUNCT
eurjchem-1645	268	36	2h	2h	NUM
eurjchem-1645	268	37	,	,	PUNCT
eurjchem-1645	268	38	ch2	ch2	PROPN
eurjchem-1645	268	39	)	)	PUNCT
eurjchem-1645	268	40	,	,	PUNCT
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eurjchem-1645	268	42	(	(	PUNCT
eurjchem-1645	268	43	s	s	PROPN
eurjchem-1645	268	44	,	,	PUNCT
eurjchem-1645	268	45	3h	3h	NUM
eurjchem-1645	268	46	,	,	PUNCT
eurjchem-1645	268	47	o‐ch3	o‐ch3	PROPN
eurjchem-1645	268	48	)	)	PUNCT
eurjchem-1645	268	49	,	,	PUNCT
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eurjchem-1645	268	52	d	d	PROPN
eurjchem-1645	268	53	,	,	PUNCT
eurjchem-1645	268	54	2h	2h	NUM
eurjchem-1645	268	55	,	,	PUNCT
eurjchem-1645	268	56	j	j	PROPN
eurjchem-1645	268	57	=	=	SYM
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eurjchem-1645	268	59	hz	hz	NOUN
eurjchem-1645	268	60	,	,	PUNCT
eurjchem-1645	268	61	n‐ch2	n‐ch2	PROPN
eurjchem-1645	268	62	)	)	PUNCT
eurjchem-1645	268	63	,	,	PUNCT
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eurjchem-1645	268	69	,	,	PUNCT
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eurjchem-1645	268	71	=	=	SYM
eurjchem-1645	268	72	7.6	7.6	NUM
eurjchem-1645	268	73	hz	hz	NOUN
eurjchem-1645	268	74	,	,	PUNCT
eurjchem-1645	268	75	ar‐h	ar‐h	PROPN
eurjchem-1645	268	76	)	)	PUNCT
eurjchem-1645	268	77	,	,	PUNCT
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eurjchem-1645	268	79	(	(	PUNCT
eurjchem-1645	268	80	s	s	PROPN
eurjchem-1645	268	81	,	,	PUNCT
eurjchem-1645	268	82	1h	1h	NUM
eurjchem-1645	268	83	,	,	PUNCT
eurjchem-1645	268	84	ar‐h	ar‐h	NOUN
eurjchem-1645	268	85	)	)	PUNCT
eurjchem-1645	268	86	,	,	PUNCT
eurjchem-1645	268	87	6.66	6.66	NUM
eurjchem-1645	268	88	(	(	PUNCT
eurjchem-1645	268	89	t	t	PROPN
eurjchem-1645	268	90	,	,	PUNCT
eurjchem-1645	268	91	1h	1h	NUM
eurjchem-1645	268	92	,	,	PUNCT
eurjchem-1645	268	93	j	j	PROPN
eurjchem-1645	268	94	=	=	SYM
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eurjchem-1645	268	97	,	,	PUNCT
eurjchem-1645	268	98	ar‐h	ar‐h	PROPN
eurjchem-1645	268	99	)	)	PUNCT
eurjchem-1645	268	100	,	,	PUNCT
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eurjchem-1645	268	103	d	d	PROPN
eurjchem-1645	268	104	,	,	PUNCT
eurjchem-1645	268	105	1h	1h	NUM
eurjchem-1645	268	106	,	,	PUNCT
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eurjchem-1645	268	111	,	,	PUNCT
eurjchem-1645	268	112	ar‐h	ar‐h	PROPN
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eurjchem-1645	268	114	,	,	PUNCT
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eurjchem-1645	268	117	m	m	PROPN
eurjchem-1645	268	118	,	,	PUNCT
eurjchem-1645	268	119	2h	2h	NUM
eurjchem-1645	268	120	,	,	PUNCT
eurjchem-1645	268	121	ar‐h	ar‐h	NOUN
eurjchem-1645	268	122	)	)	PUNCT
eurjchem-1645	268	123	,	,	PUNCT
eurjchem-1645	268	124	8.18‐8.01	8.18‐8.01	NUM
eurjchem-1645	268	125	(	(	PUNCT
eurjchem-1645	268	126	m	m	PROPN
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eurjchem-1645	268	128	2h	2h	NUM
eurjchem-1645	268	129	,	,	PUNCT
eurjchem-1645	268	130	ar‐h	ar‐h	NOUN
eurjchem-1645	268	131	)	)	PUNCT
eurjchem-1645	268	132	,	,	PUNCT
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eurjchem-1645	268	135	s	s	PROPN
eurjchem-1645	268	136	,	,	PUNCT
eurjchem-1645	268	137	1h	1h	NUM
eurjchem-1645	268	138	,	,	PUNCT
eurjchem-1645	268	139	ar‐h	ar‐h	NOUN
eurjchem-1645	268	140	)	)	PUNCT
eurjchem-1645	268	141	,	,	PUNCT
eurjchem-1645	268	142	9.38	9.38	NUM
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eurjchem-1645	268	144	s	s	PROPN
eurjchem-1645	268	145	,	,	PUNCT
eurjchem-1645	268	146	1h	1h	NUM
eurjchem-1645	268	147	,	,	PUNCT
eurjchem-1645	268	148	ar‐h	ar‐h	NOUN
eurjchem-1645	268	149	)	)	PUNCT
eurjchem-1645	268	150	,	,	PUNCT
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eurjchem-1645	268	154	,	,	PUNCT
eurjchem-1645	268	155	1h	1h	NUM
eurjchem-1645	268	156	,	,	PUNCT
eurjchem-1645	268	157	ar‐h	ar‐h	NOUN
eurjchem-1645	268	158	)	)	PUNCT
eurjchem-1645	268	159	.	.	PUNCT
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eurjchem-1645	269	2	(	(	PUNCT
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eurjchem-1645	269	11	m+h	m+h	NOUN
eurjchem-1645	269	12	)	)	PUNCT
eurjchem-1645	269	13	.	.	PUNCT
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eurjchem-1645	271	4	c	c	X
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eurjchem-1645	271	13	,	,	PUNCT
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eurjchem-1645	271	17	:	:	PUNCT
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eurjchem-1645	272	2	,	,	PUNCT
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eurjchem-1645	272	4	;	;	PUNCT
eurjchem-1645	272	5	h	h	NOUN
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eurjchem-1645	272	9	n	n	CCONJ
eurjchem-1645	272	10	,	,	PUNCT
eurjchem-1645	272	11	12.26	12.26	NUM
eurjchem-1645	272	12	%	%	NOUN
eurjchem-1645	272	13	.	.	PUNCT
eurjchem-1645	273	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	273	2	3‐(benzofuran‐2‐yl)‐4,5,6,7‐tetrahydro‐6‐(pyrimi	3‐(benzofuran‐2‐yl)‐4,5,6,7‐tetrahydro‐6‐(pyrimi	NUM
eurjchem-1645	273	3	din‐2‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	din‐2‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	X
eurjchem-1645	273	4	(	(	PUNCT
eurjchem-1645	273	5	12e	12e	NUM
eurjchem-1645	273	6	):	):	PUNCT
eurjchem-1645	273	7	color	color	NOUN
eurjchem-1645	273	8	:	:	PUNCT
eurjchem-1645	273	9	white	white	ADJ
eurjchem-1645	273	10	.	.	PUNCT
eurjchem-1645	274	1	yield	yield	NOUN
eurjchem-1645	274	2	:	:	PUNCT
eurjchem-1645	274	3	86	86	NUM
eurjchem-1645	274	4	%	%	NOUN
eurjchem-1645	274	5	.	.	PUNCT
eurjchem-1645	275	1	m.p	m.p	PROPN
eurjchem-1645	275	2	.	.	PROPN
eurjchem-1645	275	3	:	:	PUNCT
eurjchem-1645	276	1	155‐156	155‐156	NUM
eurjchem-1645	276	2	°	°	PROPN
eurjchem-1645	276	3	c	c	X
eurjchem-1645	276	4	.	.	PUNCT
eurjchem-1645	276	5	1h	1h	NUM
eurjchem-1645	276	6	nmr	nmr	NOUN
eurjchem-1645	276	7	(	(	PUNCT
eurjchem-1645	276	8	400	400	NUM
eurjchem-1645	276	9	mhz	mhz	NOUN
eurjchem-1645	276	10	,	,	PUNCT
eurjchem-1645	276	11	dmso‐	dmso‐	NUM
eurjchem-1645	276	12	d6	d6	NOUN
eurjchem-1645	276	13	,	,	PUNCT
eurjchem-1645	276	14	δ	δ	PROPN
eurjchem-1645	276	15	,	,	PUNCT
eurjchem-1645	276	16	ppm	ppm	NUM
eurjchem-1645	276	17	):	):	PUNCT
eurjchem-1645	276	18	1.38	1.38	NUM
eurjchem-1645	276	19	(	(	PUNCT
eurjchem-1645	276	20	s	s	PROPN
eurjchem-1645	276	21	,	,	PUNCT
eurjchem-1645	276	22	9h	9h	NUM
eurjchem-1645	276	23	,	,	PUNCT
eurjchem-1645	276	24	t‐bu	t‐bu	NOUN
eurjchem-1645	276	25	)	)	PUNCT
eurjchem-1645	276	26	,	,	PUNCT
eurjchem-1645	276	27	2.86	2.86	NUM
eurjchem-1645	276	28	(	(	PUNCT
eurjchem-1645	276	29	d	d	PROPN
eurjchem-1645	276	30	,	,	PUNCT
eurjchem-1645	276	31	2h	2h	NUM
eurjchem-1645	276	32	,	,	PUNCT
eurjchem-1645	276	33	j	j	PROPN
eurjchem-1645	276	34	=	=	SYM
eurjchem-1645	276	35	8hz	8hz	NOUN
eurjchem-1645	276	36	,	,	PUNCT
eurjchem-1645	276	37	ch2	ch2	PROPN
eurjchem-1645	276	38	)	)	PUNCT
eurjchem-1645	276	39	,	,	PUNCT
eurjchem-1645	276	40	4.08	4.08	NUM
eurjchem-1645	276	41	(	(	PUNCT
eurjchem-1645	276	42	s	s	PROPN
eurjchem-1645	276	43	,	,	PUNCT
eurjchem-1645	276	44	2h	2h	NUM
eurjchem-1645	276	45	,	,	PUNCT
eurjchem-1645	276	46	ch2	ch2	PROPN
eurjchem-1645	276	47	)	)	PUNCT
eurjchem-1645	276	48	,	,	PUNCT
eurjchem-1645	276	49	4.96	4.96	NUM
eurjchem-1645	276	50	(	(	PUNCT
eurjchem-1645	276	51	d	d	NOUN
eurjchem-1645	276	52	,	,	PUNCT
eurjchem-1645	276	53	2h	2h	NUM
eurjchem-1645	276	54	,	,	PUNCT
eurjchem-1645	276	55	j	j	PROPN
eurjchem-1645	276	56	=	=	SYM
eurjchem-1645	276	57	7.8	7.8	NUM
eurjchem-1645	276	58	hz	hz	NOUN
eurjchem-1645	276	59	,	,	PUNCT
eurjchem-1645	276	60	n‐ch2	n‐ch2	PROPN
eurjchem-1645	276	61	)	)	PUNCT
eurjchem-1645	276	62	,	,	PUNCT
eurjchem-1645	276	63	6.60	6.60	NUM
eurjchem-1645	276	64	(	(	PUNCT
eurjchem-1645	276	65	s	s	PROPN
eurjchem-1645	276	66	,	,	PUNCT
eurjchem-1645	276	67	1h	1h	NUM
eurjchem-1645	276	68	,	,	PUNCT
eurjchem-1645	276	69	ar‐h	ar‐h	NOUN
eurjchem-1645	276	70	)	)	PUNCT
eurjchem-1645	276	71	,	,	PUNCT
eurjchem-1645	276	72	7.18‐7.02	7.18‐7.02	NUM
eurjchem-1645	276	73	(	(	PUNCT
eurjchem-1645	276	74	d	d	PROPN
eurjchem-1645	276	75	,	,	PUNCT
eurjchem-1645	276	76	1h	1h	NUM
eurjchem-1645	276	77	,	,	PUNCT
eurjchem-1645	276	78	ar‐h	ar‐h	NOUN
eurjchem-1645	276	79	)	)	PUNCT
eurjchem-1645	276	80	,	,	PUNCT
eurjchem-1645	276	81	7.49‐7.20	7.49‐7.20	NUM
eurjchem-1645	276	82	(	(	PUNCT
eurjchem-1645	276	83	m	m	PROPN
eurjchem-1645	276	84	,	,	PUNCT
eurjchem-1645	276	85	2h	2h	NUM
eurjchem-1645	276	86	,	,	PUNCT
eurjchem-1645	276	87	ar‐h	ar‐h	NOUN
eurjchem-1645	276	88	)	)	PUNCT
eurjchem-1645	276	89	,	,	PUNCT
eurjchem-1645	276	90	7.76‐7.10	7.76‐7.10	NUM
eurjchem-1645	276	91	(	(	PUNCT
eurjchem-1645	276	92	m	m	PROPN
eurjchem-1645	276	93	,	,	PUNCT
eurjchem-1645	276	94	2h	2h	NUM
eurjchem-1645	276	95	,	,	PUNCT
eurjchem-1645	276	96	ar‐h	ar‐h	NOUN
eurjchem-1645	276	97	)	)	PUNCT
eurjchem-1645	276	98	,	,	PUNCT
eurjchem-1645	276	99	8.42	8.42	NUM
eurjchem-1645	276	100	(	(	PUNCT
eurjchem-1645	276	101	s	s	PROPN
eurjchem-1645	276	102	,	,	PUNCT
eurjchem-1645	276	103	2h	2h	NUM
eurjchem-1645	276	104	,	,	PUNCT
eurjchem-1645	276	105	ar‐h	ar‐h	NOUN
eurjchem-1645	276	106	)	)	PUNCT
eurjchem-1645	276	107	.	.	PUNCT
eurjchem-1645	277	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	277	2	(	(	PUNCT
eurjchem-1645	277	3	ei	ei	X
eurjchem-1645	277	4	,	,	PUNCT
eurjchem-1645	277	5	m	m	PROPN
eurjchem-1645	277	6	/	/	SYM
eurjchem-1645	277	7	z	z	NOUN
eurjchem-1645	277	8	):	):	PUNCT
eurjchem-1645	277	9	418	418	NUM
eurjchem-1645	277	10	(	(	PUNCT
eurjchem-1645	277	11	m+h	m+h	NOUN
eurjchem-1645	277	12	)	)	PUNCT
eurjchem-1645	277	13	.	.	PUNCT
eurjchem-1645	278	1	anal	anal	PROPN
eurjchem-1645	278	2	.	.	PUNCT
eurjchem-1645	278	3	calcd	calcd	NOUN
eurjchem-1645	278	4	.	.	PUNCT
eurjchem-1645	279	1	for	for	ADP
eurjchem-1645	279	2	c23h23n5o3	c23h23n5o3	PROPN
eurjchem-1645	279	3	:	:	PUNCT
eurjchem-1645	279	4	c	c	X
eurjchem-1645	279	5	,	,	PUNCT
eurjchem-1645	279	6	66.17	66.17	NUM
eurjchem-1645	279	7	;	;	PUNCT
eurjchem-1645	279	8	h	h	NOUN
eurjchem-1645	279	9	,	,	PUNCT
eurjchem-1645	279	10	5.55	5.55	NUM
eurjchem-1645	279	11	;	;	PUNCT
eurjchem-1645	279	12	n	n	CCONJ
eurjchem-1645	279	13	,	,	PUNCT
eurjchem-1645	279	14	16.78	16.78	NUM
eurjchem-1645	279	15	.	.	PUNCT
eurjchem-1645	280	1	found	find	VERB
eurjchem-1645	280	2	:	:	PUNCT
eurjchem-1645	281	1	c	c	X
eurjchem-1645	281	2	,	,	PUNCT
eurjchem-1645	281	3	66.15	66.15	NUM
eurjchem-1645	281	4	;	;	PUNCT
eurjchem-1645	281	5	h	h	NOUN
eurjchem-1645	281	6	,	,	PUNCT
eurjchem-1645	281	7	5.53	5.53	NUM
eurjchem-1645	281	8	;	;	PUNCT
eurjchem-1645	281	9	n	n	CCONJ
eurjchem-1645	281	10	,	,	PUNCT
eurjchem-1645	281	11	16.79	16.79	NUM
eurjchem-1645	281	12	%	%	NOUN
eurjchem-1645	281	13	.	.	PUNCT
eurjchem-1645	282	1	tert‐butyl	tert‐butyl	PRON
eurjchem-1645	282	2	3‐(benzo[b]thiophen‐2‐yl)‐4,5,6,7‐tetrahydro‐6‐	3‐(benzo[b]thiophen‐2‐yl)‐4,5,6,7‐tetrahydro‐6‐	NOUN
eurjchem-1645	282	3	(	(	PUNCT
eurjchem-1645	282	4	pyrimidin‐2‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	pyrimidin‐2‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	PROPN
eurjchem-1645	282	5	(	(	PUNCT
eurjchem-1645	282	6	12f	12f	NUM
eurjchem-1645	282	7	):	):	PUNCT
eurjchem-1645	282	8	color	color	NOUN
eurjchem-1645	282	9	:	:	PUNCT
eurjchem-1645	282	10	white	white	ADJ
eurjchem-1645	282	11	.	.	PUNCT
eurjchem-1645	282	12	yield	yield	NOUN
eurjchem-1645	282	13	:	:	PUNCT
eurjchem-1645	282	14	84	84	NUM
eurjchem-1645	282	15	%	%	NOUN
eurjchem-1645	282	16	.	.	PUNCT
eurjchem-1645	283	1	m.p	m.p	PROPN
eurjchem-1645	283	2	.	.	PROPN
eurjchem-1645	283	3	:	:	PUNCT
eurjchem-1645	284	1	154‐155	154‐155	NUM
eurjchem-1645	284	2	°	°	PROPN
eurjchem-1645	284	3	c	c	PROPN
eurjchem-1645	284	4	.	.	PUNCT
eurjchem-1645	284	5	1h	1h	NUM
eurjchem-1645	284	6	nmr	nmr	NOUN
eurjchem-1645	284	7	(	(	PUNCT
eurjchem-1645	284	8	400	400	NUM
eurjchem-1645	284	9	mhz	mhz	NOUN
eurjchem-1645	284	10	,	,	PUNCT
eurjchem-1645	284	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	284	12	,	,	PUNCT
eurjchem-1645	284	13	δ	δ	PROPN
eurjchem-1645	284	14	,	,	PUNCT
eurjchem-1645	284	15	ppm	ppm	NUM
eurjchem-1645	284	16	):	):	PUNCT
eurjchem-1645	284	17	1.38	1.38	NUM
eurjchem-1645	284	18	(	(	PUNCT
eurjchem-1645	284	19	s	s	PROPN
eurjchem-1645	284	20	,	,	PUNCT
eurjchem-1645	284	21	9h	9h	NUM
eurjchem-1645	284	22	,	,	PUNCT
eurjchem-1645	284	23	t‐bu	t‐bu	NOUN
eurjchem-1645	284	24	)	)	PUNCT
eurjchem-1645	284	25	,	,	PUNCT
eurjchem-1645	284	26	3.06	3.06	NUM
eurjchem-1645	284	27	(	(	PUNCT
eurjchem-1645	284	28	d	d	PROPN
eurjchem-1645	284	29	,	,	PUNCT
eurjchem-1645	284	30	2h	2h	NUM
eurjchem-1645	284	31	,	,	PUNCT
eurjchem-1645	284	32	j	j	PROPN
eurjchem-1645	284	33	=	=	PROPN
eurjchem-1645	284	34	8.2	8.2	NUM
eurjchem-1645	284	35	hz	hz	NOUN
eurjchem-1645	284	36	,	,	PUNCT
eurjchem-1645	284	37	ch2	ch2	PROPN
eurjchem-1645	284	38	)	)	PUNCT
eurjchem-1645	284	39	,	,	PUNCT
eurjchem-1645	284	40	4.18	4.18	NUM
eurjchem-1645	284	41	(	(	PUNCT
eurjchem-1645	284	42	s	s	PROPN
eurjchem-1645	284	43	,	,	PUNCT
eurjchem-1645	284	44	2h	2h	NUM
eurjchem-1645	284	45	,	,	PUNCT
eurjchem-1645	284	46	ch2	ch2	PROPN
eurjchem-1645	284	47	)	)	PUNCT
eurjchem-1645	284	48	,	,	PUNCT
eurjchem-1645	284	49	4.96	4.96	NUM
eurjchem-1645	284	50	(	(	PUNCT
eurjchem-1645	284	51	d	d	NOUN
eurjchem-1645	284	52	,	,	PUNCT
eurjchem-1645	284	53	2h	2h	NUM
eurjchem-1645	284	54	,	,	PUNCT
eurjchem-1645	284	55	j	j	PROPN
eurjchem-1645	284	56	=	=	SYM
eurjchem-1645	284	57	7.6	7.6	NUM
eurjchem-1645	284	58	hz	hz	NOUN
eurjchem-1645	284	59	,	,	PUNCT
eurjchem-1645	284	60	n‐ch2	n‐ch2	PROPN
eurjchem-1645	284	61	)	)	PUNCT
eurjchem-1645	284	62	,	,	PUNCT
eurjchem-1645	284	63	6.56	6.56	NUM
eurjchem-1645	284	64	(	(	PUNCT
eurjchem-1645	284	65	s	s	PROPN
eurjchem-1645	284	66	,	,	PUNCT
eurjchem-1645	284	67	1h	1h	NUM
eurjchem-1645	284	68	,	,	PUNCT
eurjchem-1645	284	69	ar‐h	ar‐h	NOUN
eurjchem-1645	284	70	)	)	PUNCT
eurjchem-1645	284	71	,	,	PUNCT
eurjchem-1645	284	72	7.16‐7.02	7.16‐7.02	NUM
eurjchem-1645	284	73	(	(	PUNCT
eurjchem-1645	284	74	d	d	PROPN
eurjchem-1645	284	75	,	,	PUNCT
eurjchem-1645	284	76	1h	1h	NUM
eurjchem-1645	284	77	,	,	PUNCT
eurjchem-1645	284	78	ar‐h	ar‐h	NOUN
eurjchem-1645	284	79	)	)	PUNCT
eurjchem-1645	284	80	,	,	PUNCT
eurjchem-1645	284	81	7.49‐7.14	7.49‐7.14	NUM
eurjchem-1645	284	82	(	(	PUNCT
eurjchem-1645	284	83	m	m	PROPN
eurjchem-1645	284	84	,	,	PUNCT
eurjchem-1645	284	85	2h	2h	NUM
eurjchem-1645	284	86	,	,	PUNCT
eurjchem-1645	284	87	ar‐h	ar‐h	NOUN
eurjchem-1645	284	88	)	)	PUNCT
eurjchem-1645	284	89	,	,	PUNCT
eurjchem-1645	284	90	7.86‐7.54	7.86‐7.54	NUM
eurjchem-1645	284	91	(	(	PUNCT
eurjchem-1645	284	92	m	m	PROPN
eurjchem-1645	284	93	,	,	PUNCT
eurjchem-1645	284	94	2h	2h	NUM
eurjchem-1645	284	95	,	,	PUNCT
eurjchem-1645	284	96	ar‐h	ar‐h	NOUN
eurjchem-1645	284	97	)	)	PUNCT
eurjchem-1645	284	98	,	,	PUNCT
eurjchem-1645	284	99	8.54	8.54	NUM
eurjchem-1645	284	100	(	(	PUNCT
eurjchem-1645	284	101	s	s	PROPN
eurjchem-1645	284	102	,	,	PUNCT
eurjchem-1645	284	103	2h	2h	NUM
eurjchem-1645	284	104	,	,	PUNCT
eurjchem-1645	284	105	ar‐h	ar‐h	NOUN
eurjchem-1645	284	106	)	)	PUNCT
eurjchem-1645	284	107	.	.	PUNCT
eurjchem-1645	285	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	285	2	(	(	PUNCT
eurjchem-1645	285	3	ei	ei	X
eurjchem-1645	285	4	,	,	PUNCT
eurjchem-1645	285	5	m	m	PROPN
eurjchem-1645	285	6	/	/	SYM
eurjchem-1645	285	7	z	z	NOUN
eurjchem-1645	285	8	):	):	PUNCT
eurjchem-1645	285	9	434	434	NUM
eurjchem-1645	285	10	(	(	PUNCT
eurjchem-1645	285	11	m+h	m+h	NOUN
eurjchem-1645	285	12	)	)	PUNCT
eurjchem-1645	285	13	.	.	PUNCT
eurjchem-1645	286	1	anal	anal	PROPN
eurjchem-1645	286	2	.	.	PUNCT
eurjchem-1645	286	3	calcd	calcd	NOUN
eurjchem-1645	286	4	.	.	PUNCT
eurjchem-1645	287	1	for	for	ADP
eurjchem-1645	287	2	c23h23n5o2s	c23h23n5o2s	PROPN
eurjchem-1645	287	3	:	:	PUNCT
eurjchem-1645	287	4	c	c	X
eurjchem-1645	287	5	,	,	PUNCT
eurjchem-1645	287	6	63.72	63.72	NUM
eurjchem-1645	287	7	;	;	PUNCT
eurjchem-1645	287	8	h	h	NOUN
eurjchem-1645	287	9	,	,	PUNCT
eurjchem-1645	287	10	5.35	5.35	NUM
eurjchem-1645	287	11	;	;	PUNCT
eurjchem-1645	287	12	n	n	CCONJ
eurjchem-1645	287	13	,	,	PUNCT
eurjchem-1645	287	14	16.15	16.15	NUM
eurjchem-1645	287	15	.	.	PUNCT
eurjchem-1645	287	16	found	find	VERB
eurjchem-1645	287	17	:	:	PUNCT
eurjchem-1645	288	1	c	c	X
eurjchem-1645	288	2	,	,	PUNCT
eurjchem-1645	288	3	63.71	63.71	NUM
eurjchem-1645	288	4	;	;	PUNCT
eurjchem-1645	288	5	h	h	NOUN
eurjchem-1645	288	6	,	,	PUNCT
eurjchem-1645	288	7	5.37	5.37	NUM
eurjchem-1645	288	8	;	;	PUNCT
eurjchem-1645	288	9	n	n	CCONJ
eurjchem-1645	288	10	,	,	PUNCT
eurjchem-1645	288	11	16.16	16.16	NUM
eurjchem-1645	288	12	%	%	NOUN
eurjchem-1645	288	13	.	.	PUNCT
eurjchem-1645	289	1	tert‐butyl	tert‐butyl	PUNCT
eurjchem-1645	289	2	4,5,6,7‐tetrahydro‐6‐(pyrimidin‐2‐yl)‐3‐(quinolin‐	4,5,6,7‐tetrahydro‐6‐(pyrimidin‐2‐yl)‐3‐(quinolin‐	NUM
eurjchem-1645	289	3	3‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	3‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	289	4	(	(	PUNCT
eurjchem-1645	289	5	12	12	NUM
eurjchem-1645	289	6	g	g	NOUN
eurjchem-1645	289	7	):	):	PUNCT
eurjchem-1645	289	8	color	color	NOUN
eurjchem-1645	289	9	:	:	PUNCT
eurjchem-1645	289	10	white	white	ADJ
eurjchem-1645	289	11	.	.	PUNCT
eurjchem-1645	290	1	yield	yield	NOUN
eurjchem-1645	290	2	:	:	PUNCT
eurjchem-1645	290	3	84	84	NUM
eurjchem-1645	290	4	%	%	NOUN
eurjchem-1645	290	5	.	.	PUNCT
eurjchem-1645	291	1	m.p	m.p	PROPN
eurjchem-1645	291	2	.	.	PROPN
eurjchem-1645	291	3	:	:	PUNCT
eurjchem-1645	292	1	165‐166	165‐166	NUM
eurjchem-1645	292	2	°	°	PROPN
eurjchem-1645	292	3	c	c	PROPN
eurjchem-1645	292	4	.	.	PUNCT
eurjchem-1645	293	1	1h	1h	NUM
eurjchem-1645	293	2	nmr	nmr	NOUN
eurjchem-1645	293	3	(	(	PUNCT
eurjchem-1645	293	4	400	400	NUM
eurjchem-1645	293	5	mhz	mhz	NOUN
eurjchem-1645	293	6	,	,	PUNCT
eurjchem-1645	293	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	293	8	,	,	PUNCT
eurjchem-1645	293	9	δ	δ	PROPN
eurjchem-1645	293	10	,	,	PUNCT
eurjchem-1645	293	11	ppm	ppm	NUM
eurjchem-1645	293	12	):	):	PUNCT
eurjchem-1645	293	13	1.38	1.38	NUM
eurjchem-1645	293	14	(	(	PUNCT
eurjchem-1645	293	15	s	s	PROPN
eurjchem-1645	293	16	,	,	PUNCT
eurjchem-1645	293	17	9h	9h	NUM
eurjchem-1645	293	18	,	,	PUNCT
eurjchem-1645	293	19	t‐bu	t‐bu	NOUN
eurjchem-1645	293	20	)	)	PUNCT
eurjchem-1645	293	21	,	,	PUNCT
eurjchem-1645	293	22	2.92	2.92	NUM
eurjchem-1645	293	23	(	(	PUNCT
eurjchem-1645	293	24	d	d	PROPN
eurjchem-1645	293	25	,	,	PUNCT
eurjchem-1645	293	26	2h	2h	NUM
eurjchem-1645	293	27	,	,	PUNCT
eurjchem-1645	293	28	j	j	PROPN
eurjchem-1645	293	29	=	=	PROPN
eurjchem-1645	293	30	8.4	8.4	NUM
eurjchem-1645	293	31	hz	hz	NOUN
eurjchem-1645	293	32	,	,	PUNCT
eurjchem-1645	293	33	ch2	ch2	PROPN
eurjchem-1645	293	34	)	)	PUNCT
eurjchem-1645	293	35	,	,	PUNCT
eurjchem-1645	293	36	4.12	4.12	NUM
eurjchem-1645	293	37	(	(	PUNCT
eurjchem-1645	293	38	q	q	NOUN
eurjchem-1645	293	39	,	,	PUNCT
eurjchem-1645	293	40	2h	2h	NUM
eurjchem-1645	293	41	,	,	PUNCT
eurjchem-1645	293	42	j	j	PROPN
eurjchem-1645	293	43	=	=	PROPN
eurjchem-1645	293	44	8.4	8.4	NUM
eurjchem-1645	293	45	hz	hz	NOUN
eurjchem-1645	293	46	,	,	PUNCT
eurjchem-1645	293	47	ch2	ch2	PROPN
eurjchem-1645	293	48	)	)	PUNCT
eurjchem-1645	293	49	,	,	PUNCT
eurjchem-1645	293	50	4.94	4.94	NUM
eurjchem-1645	293	51	(	(	PUNCT
eurjchem-1645	293	52	s	s	PROPN
eurjchem-1645	293	53	,	,	PUNCT
eurjchem-1645	293	54	2h	2h	NUM
eurjchem-1645	293	55	,	,	PUNCT
eurjchem-1645	293	56	n‐ch2	n‐ch2	PROPN
eurjchem-1645	293	57	)	)	PUNCT
eurjchem-1645	293	58	,	,	PUNCT
eurjchem-1645	293	59	6.72	6.72	NUM
eurjchem-1645	293	60	(	(	PUNCT
eurjchem-1645	293	61	t	t	PROPN
eurjchem-1645	293	62	,	,	PUNCT
eurjchem-1645	293	63	1h	1h	NUM
eurjchem-1645	293	64	,	,	PUNCT
eurjchem-1645	293	65	j	j	PROPN
eurjchem-1645	293	66	=	=	SYM
eurjchem-1645	293	67	7.6	7.6	NUM
eurjchem-1645	293	68	hz	hz	NOUN
eurjchem-1645	293	69	,	,	PUNCT
eurjchem-1645	293	70	ar‐h	ar‐h	NOUN
eurjchem-1645	293	71	)	)	PUNCT
eurjchem-1645	293	72	,	,	PUNCT
eurjchem-1645	293	73	7.74	7.74	NUM
eurjchem-1645	293	74	(	(	PUNCT
eurjchem-1645	293	75	t	t	PROPN
eurjchem-1645	293	76	,	,	PUNCT
eurjchem-1645	293	77	1h	1h	NUM
eurjchem-1645	293	78	,	,	PUNCT
eurjchem-1645	293	79	j	j	PROPN
eurjchem-1645	293	80	=	=	SYM
eurjchem-1645	293	81	8	8	NUM
eurjchem-1645	293	82	hz	hz	NOUN
eurjchem-1645	293	83	,	,	PUNCT
eurjchem-1645	293	84	ar‐h	ar‐h	NOUN
eurjchem-1645	293	85	)	)	PUNCT
eurjchem-1645	293	86	,	,	PUNCT
eurjchem-1645	293	87	7.84	7.84	NUM
eurjchem-1645	293	88	(	(	PUNCT
eurjchem-1645	293	89	t	t	PROPN
eurjchem-1645	293	90	,	,	PUNCT
eurjchem-1645	293	91	1h	1h	NUM
eurjchem-1645	293	92	,	,	PUNCT
eurjchem-1645	293	93	j	j	PROPN
eurjchem-1645	293	94	=	=	SYM
eurjchem-1645	293	95	8	8	NUM
eurjchem-1645	293	96	hz	hz	NOUN
eurjchem-1645	293	97	,	,	PUNCT
eurjchem-1645	293	98	ar‐h	ar‐h	PROPN
eurjchem-1645	293	99	)	)	PUNCT
eurjchem-1645	293	100	,	,	PUNCT
eurjchem-1645	293	101	8.12	8.12	NUM
eurjchem-1645	293	102	(	(	PUNCT
eurjchem-1645	293	103	d	d	PROPN
eurjchem-1645	293	104	,	,	PUNCT
eurjchem-1645	293	105	1h	1h	NUM
eurjchem-1645	293	106	,	,	PUNCT
eurjchem-1645	293	107	j	j	PROPN
eurjchem-1645	293	108	=	=	SYM
eurjchem-1645	293	109	7.8	7.8	NUM
eurjchem-1645	293	110	hz	hz	NOUN
eurjchem-1645	293	111	,	,	PUNCT
eurjchem-1645	293	112	ar‐h	ar‐h	PROPN
eurjchem-1645	293	113	)	)	PUNCT
eurjchem-1645	293	114	,	,	PUNCT
eurjchem-1645	293	115	8.22	8.22	NUM
eurjchem-1645	293	116	(	(	PUNCT
eurjchem-1645	293	117	d	d	PROPN
eurjchem-1645	293	118	,	,	PUNCT
eurjchem-1645	293	119	1h	1h	NUM
eurjchem-1645	293	120	,	,	PUNCT
eurjchem-1645	293	121	j	j	PROPN
eurjchem-1645	293	122	=	=	SYM
eurjchem-1645	293	123	7.8	7.8	NUM
eurjchem-1645	293	124	hz	hz	NOUN
eurjchem-1645	293	125	,	,	PUNCT
eurjchem-1645	293	126	ar‐h	ar‐h	PROPN
eurjchem-1645	293	127	)	)	PUNCT
eurjchem-1645	293	128	,	,	PUNCT
eurjchem-1645	293	129	8.42	8.42	NUM
eurjchem-1645	293	130	(	(	PUNCT
eurjchem-1645	293	131	d	d	PROPN
eurjchem-1645	293	132	,	,	PUNCT
eurjchem-1645	293	133	1h	1h	NUM
eurjchem-1645	293	134	,	,	PUNCT
eurjchem-1645	293	135	j	j	PROPN
eurjchem-1645	293	136	=	=	SYM
eurjchem-1645	293	137	7.6	7.6	NUM
eurjchem-1645	293	138	hz	hz	NOUN
eurjchem-1645	293	139	,	,	PUNCT
eurjchem-1645	293	140	ar‐h	ar‐h	PROPN
eurjchem-1645	293	141	)	)	PUNCT
eurjchem-1645	293	142	,	,	PUNCT
eurjchem-1645	293	143	8.56	8.56	NUM
eurjchem-1645	293	144	(	(	PUNCT
eurjchem-1645	293	145	s	s	PROPN
eurjchem-1645	293	146	,	,	PUNCT
eurjchem-1645	293	147	1h	1h	NUM
eurjchem-1645	293	148	,	,	PUNCT
eurjchem-1645	293	149	ar‐h	ar‐h	NOUN
eurjchem-1645	293	150	)	)	PUNCT
eurjchem-1645	293	151	,	,	PUNCT
eurjchem-1645	293	152	9.38‐9.22	9.38‐9.22	NUM
eurjchem-1645	293	153	(	(	PUNCT
eurjchem-1645	293	154	br	br	NOUN
eurjchem-1645	293	155	,	,	PUNCT
eurjchem-1645	293	156	2h	2h	NUM
eurjchem-1645	293	157	,	,	PUNCT
eurjchem-1645	293	158	ar‐h	ar‐h	NOUN
eurjchem-1645	293	159	)	)	PUNCT
eurjchem-1645	293	160	.	.	PUNCT
eurjchem-1645	294	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	294	2	(	(	PUNCT
eurjchem-1645	294	3	ei	ei	X
eurjchem-1645	294	4	,	,	PUNCT
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eurjchem-1645	294	6	/	/	SYM
eurjchem-1645	294	7	z	z	NOUN
eurjchem-1645	294	8	):	):	PUNCT
eurjchem-1645	294	9	429	429	NUM
eurjchem-1645	294	10	(	(	PUNCT
eurjchem-1645	294	11	m+h	m+h	NOUN
eurjchem-1645	294	12	)	)	PUNCT
eurjchem-1645	294	13	.	.	PUNCT
eurjchem-1645	295	1	anal	anal	PROPN
eurjchem-1645	295	2	.	.	PUNCT
eurjchem-1645	295	3	calcd	calcd	NOUN
eurjchem-1645	295	4	.	.	PUNCT
eurjchem-1645	296	1	for	for	ADP
eurjchem-1645	296	2	c24h24n4o2	c24h24n4o2	PROPN
eurjchem-1645	296	3	:	:	PUNCT
eurjchem-1645	296	4	c	c	NOUN
eurjchem-1645	296	5	,	,	PUNCT
eurjchem-1645	296	6	67.27	67.27	NUM
eurjchem-1645	296	7	;	;	PUNCT
eurjchem-1645	296	8	h	h	NOUN
eurjchem-1645	296	9	,	,	PUNCT
eurjchem-1645	296	10	5.65	5.65	NUM
eurjchem-1645	296	11	;	;	PUNCT
eurjchem-1645	296	12	n	n	CCONJ
eurjchem-1645	296	13	,	,	PUNCT
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eurjchem-1645	296	17	:	:	PUNCT
eurjchem-1645	297	1	c	c	X
eurjchem-1645	297	2	,	,	PUNCT
eurjchem-1645	297	3	67.25	67.25	NUM
eurjchem-1645	297	4	;	;	PUNCT
eurjchem-1645	297	5	h	h	NOUN
eurjchem-1645	297	6	,	,	PUNCT
eurjchem-1645	297	7	5.64	5.64	NUM
eurjchem-1645	297	8	;	;	PUNCT
eurjchem-1645	297	9	n	n	CCONJ
eurjchem-1645	297	10	,	,	PUNCT
eurjchem-1645	297	11	19.63	19.63	NUM
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eurjchem-1645	297	13	.	.	PUNCT
eurjchem-1645	298	1	tert‐butyl	tert‐butyl	PUNCT
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eurjchem-1645	298	3	5‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	5‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	298	4	(	(	PUNCT
eurjchem-1645	298	5	12h	12h	NUM
eurjchem-1645	298	6	):	):	PUNCT
eurjchem-1645	298	7	color	color	NOUN
eurjchem-1645	298	8	:	:	PUNCT
eurjchem-1645	298	9	yel‐	yel‐	ADJ
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eurjchem-1645	298	11	.	.	PUNCT
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eurjchem-1645	299	2	:	:	PUNCT
eurjchem-1645	299	3	93	93	NUM
eurjchem-1645	299	4	%	%	NOUN
eurjchem-1645	299	5	.	.	PUNCT
eurjchem-1645	300	1	m.p	m.p	PROPN
eurjchem-1645	300	2	.	.	PROPN
eurjchem-1645	300	3	:	:	PUNCT
eurjchem-1645	301	1	161‐162	161‐162	NUM
eurjchem-1645	301	2	°	°	SYM
eurjchem-1645	301	3	c	c	X
eurjchem-1645	301	4	.	.	PUNCT
eurjchem-1645	302	1	1h	1h	NUM
eurjchem-1645	302	2	nmr	nmr	NOUN
eurjchem-1645	302	3	(	(	PUNCT
eurjchem-1645	302	4	400	400	NUM
eurjchem-1645	302	5	mhz	mhz	NOUN
eurjchem-1645	302	6	,	,	PUNCT
eurjchem-1645	302	7	dmso‐	dmso‐	NUM
eurjchem-1645	302	8	d6	d6	NOUN
eurjchem-1645	302	9	,	,	PUNCT
eurjchem-1645	302	10	δ	δ	PROPN
eurjchem-1645	302	11	,	,	PUNCT
eurjchem-1645	302	12	ppm	ppm	NUM
eurjchem-1645	302	13	):	):	PUNCT
eurjchem-1645	302	14	1.38	1.38	NUM
eurjchem-1645	302	15	(	(	PUNCT
eurjchem-1645	302	16	s	s	PROPN
eurjchem-1645	302	17	,	,	PUNCT
eurjchem-1645	302	18	9h	9h	NUM
eurjchem-1645	302	19	,	,	PUNCT
eurjchem-1645	302	20	t‐bu	t‐bu	NOUN
eurjchem-1645	302	21	)	)	PUNCT
eurjchem-1645	302	22	,	,	PUNCT
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eurjchem-1645	302	24	(	(	PUNCT
eurjchem-1645	302	25	t	t	PROPN
eurjchem-1645	302	26	,	,	PUNCT
eurjchem-1645	302	27	2h	2h	NUM
eurjchem-1645	302	28	,	,	PUNCT
eurjchem-1645	302	29	j	j	PROPN
eurjchem-1645	302	30	=	=	PROPN
eurjchem-1645	302	31	8.2	8.2	NUM
eurjchem-1645	302	32	hz	hz	NOUN
eurjchem-1645	302	33	,	,	PUNCT
eurjchem-1645	302	34	ch2	ch2	PROPN
eurjchem-1645	302	35	)	)	PUNCT
eurjchem-1645	302	36	,	,	PUNCT
eurjchem-1645	302	37	4.04	4.04	NUM
eurjchem-1645	302	38	(	(	PUNCT
eurjchem-1645	302	39	q	q	NOUN
eurjchem-1645	302	40	,	,	PUNCT
eurjchem-1645	302	41	2h	2h	NUM
eurjchem-1645	302	42	,	,	PUNCT
eurjchem-1645	302	43	j	j	PROPN
eurjchem-1645	302	44	=	=	PROPN
eurjchem-1645	302	45	8.2	8.2	NUM
eurjchem-1645	302	46	hz	hz	NOUN
eurjchem-1645	302	47	,	,	PUNCT
eurjchem-1645	302	48	ch2	ch2	PROPN
eurjchem-1645	302	49	)	)	PUNCT
eurjchem-1645	302	50	,	,	PUNCT
eurjchem-1645	302	51	4.98	4.98	NUM
eurjchem-1645	302	52	(	(	PUNCT
eurjchem-1645	302	53	s	s	PROPN
eurjchem-1645	302	54	,	,	PUNCT
eurjchem-1645	302	55	2h	2h	NUM
eurjchem-1645	302	56	,	,	PUNCT
eurjchem-1645	302	57	n‐ch2	n‐ch2	PROPN
eurjchem-1645	302	58	)	)	PUNCT
eurjchem-1645	302	59	,	,	PUNCT
eurjchem-1645	302	60	6.66	6.66	NUM
eurjchem-1645	302	61	(	(	PUNCT
eurjchem-1645	302	62	s	s	PROPN
eurjchem-1645	302	63	,	,	PUNCT
eurjchem-1645	302	64	1h	1h	NUM
eurjchem-1645	302	65	,	,	PUNCT
eurjchem-1645	302	66	ar‐h	ar‐h	NOUN
eurjchem-1645	302	67	)	)	PUNCT
eurjchem-1645	302	68	,	,	PUNCT
eurjchem-1645	302	69	7.44	7.44	NUM
eurjchem-1645	302	70	(	(	PUNCT
eurjchem-1645	302	71	br	br	PROPN
eurjchem-1645	302	72	,	,	PUNCT
eurjchem-1645	302	73	1h	1h	NUM
eurjchem-1645	302	74	,	,	PUNCT
eurjchem-1645	302	75	ar‐h	ar‐h	NOUN
eurjchem-1645	302	76	)	)	PUNCT
eurjchem-1645	302	77	,	,	PUNCT
eurjchem-1645	302	78	7.58	7.58	NUM
eurjchem-1645	302	79	(	(	PUNCT
eurjchem-1645	302	80	d	d	PROPN
eurjchem-1645	302	81	,	,	PUNCT
eurjchem-1645	302	82	1h	1h	NUM
eurjchem-1645	302	83	,	,	PUNCT
eurjchem-1645	302	84	j	j	PROPN
eurjchem-1645	302	85	=	=	SYM
eurjchem-1645	302	86	8	8	NUM
eurjchem-1645	302	87	hz	hz	NOUN
eurjchem-1645	302	88	,	,	PUNCT
eurjchem-1645	302	89	ar‐h	ar‐h	NOUN
eurjchem-1645	302	90	)	)	PUNCT
eurjchem-1645	302	91	,	,	PUNCT
eurjchem-1645	302	92	7.83‐7.68	7.83‐7.68	NUM
eurjchem-1645	302	93	(	(	PUNCT
eurjchem-1645	302	94	m	m	PROPN
eurjchem-1645	302	95	,	,	PUNCT
eurjchem-1645	302	96	2h	2h	NUM
eurjchem-1645	302	97	,	,	PUNCT
eurjchem-1645	302	98	ar‐h	ar‐h	NOUN
eurjchem-1645	302	99	)	)	PUNCT
eurjchem-1645	302	100	,	,	PUNCT
eurjchem-1645	302	101	8.23‐8.01	8.23‐8.01	NUM
eurjchem-1645	302	102	(	(	PUNCT
eurjchem-1645	302	103	m	m	PROPN
eurjchem-1645	302	104	,	,	PUNCT
eurjchem-1645	302	105	2h	2h	NUM
eurjchem-1645	302	106	,	,	PUNCT
eurjchem-1645	302	107	ar‐h	ar‐h	NOUN
eurjchem-1645	302	108	)	)	PUNCT
eurjchem-1645	302	109	,	,	PUNCT
eurjchem-1645	302	110	8.28	8.28	NUM
eurjchem-1645	302	111	(	(	PUNCT
eurjchem-1645	302	112	s	s	PROPN
eurjchem-1645	302	113	,	,	PUNCT
eurjchem-1645	302	114	1h	1h	NUM
eurjchem-1645	302	115	,	,	PUNCT
eurjchem-1645	302	116	ar‐h	ar‐h	NOUN
eurjchem-1645	302	117	)	)	PUNCT
eurjchem-1645	302	118	,	,	PUNCT
eurjchem-1645	302	119	8.92	8.92	NUM
eurjchem-1645	302	120	(	(	PUNCT
eurjchem-1645	302	121	s	s	PROPN
eurjchem-1645	302	122	,	,	PUNCT
eurjchem-1645	302	123	1h	1h	NUM
eurjchem-1645	302	124	,	,	PUNCT
eurjchem-1645	302	125	ar‐h	ar‐h	NOUN
eurjchem-1645	302	126	)	)	PUNCT
eurjchem-1645	302	127	.	.	PUNCT
eurjchem-1645	303	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	303	2	(	(	PUNCT
eurjchem-1645	303	3	ei	ei	X
eurjchem-1645	303	4	,	,	PUNCT
eurjchem-1645	303	5	m	m	PROPN
eurjchem-1645	303	6	/	/	SYM
eurjchem-1645	303	7	z	z	NOUN
eurjchem-1645	303	8	):	):	PUNCT
eurjchem-1645	303	9	429	429	NUM
eurjchem-1645	303	10	(	(	PUNCT
eurjchem-1645	303	11	m+h	m+h	NOUN
eurjchem-1645	303	12	)	)	PUNCT
eurjchem-1645	303	13	.	.	PUNCT
eurjchem-1645	304	1	anal	anal	PROPN
eurjchem-1645	304	2	.	.	PUNCT
eurjchem-1645	304	3	calcd	calcd	NOUN
eurjchem-1645	304	4	.	.	PUNCT
eurjchem-1645	305	1	for	for	ADP
eurjchem-1645	305	2	c24h24n4o2	c24h24n4o2	PROPN
eurjchem-1645	305	3	:	:	PUNCT
eurjchem-1645	305	4	c	c	NOUN
eurjchem-1645	305	5	,	,	PUNCT
eurjchem-1645	305	6	67.27	67.27	NUM
eurjchem-1645	305	7	;	;	PUNCT
eurjchem-1645	305	8	h	h	NOUN
eurjchem-1645	305	9	,	,	PUNCT
eurjchem-1645	305	10	5.65	5.65	NUM
eurjchem-1645	305	11	;	;	PUNCT
eurjchem-1645	305	12	n	n	CCONJ
eurjchem-1645	305	13	,	,	PUNCT
eurjchem-1645	305	14	19.61	19.61	NUM
eurjchem-1645	305	15	.	.	PUNCT
eurjchem-1645	305	16	found	find	VERB
eurjchem-1645	305	17	:	:	PUNCT
eurjchem-1645	306	1	c	c	X
eurjchem-1645	306	2	,	,	PUNCT
eurjchem-1645	306	3	67.24	67.24	NUM
eurjchem-1645	306	4	;	;	PUNCT
eurjchem-1645	306	5	h	h	NOUN
eurjchem-1645	306	6	,	,	PUNCT
eurjchem-1645	306	7	5.66	5.66	NUM
eurjchem-1645	306	8	;	;	PUNCT
eurjchem-1645	306	9	n	n	CCONJ
eurjchem-1645	306	10	,	,	PUNCT
eurjchem-1645	306	11	19.64	19.64	NUM
eurjchem-1645	306	12	%	%	NOUN
eurjchem-1645	306	13	.	.	PUNCT
eurjchem-1645	307	1	2.2.12	2.2.12	X
eurjchem-1645	307	2	.	.	PUNCT
eurjchem-1645	307	3	general	general	ADJ
eurjchem-1645	307	4	procedure	procedure	NOUN
eurjchem-1645	307	5	for	for	ADP
eurjchem-1645	307	6	synthesis	synthesis	NOUN
eurjchem-1645	307	7	of	of	ADP
eurjchem-1645	307	8	compound	compound	NOUN
eurjchem-1645	307	9	13a‐h	13a‐h	NOUN
eurjchem-1645	307	10	,	,	PUNCT
eurjchem-1645	307	11	step	step	NOUN
eurjchem-1645	307	12	(	(	PUNCT
eurjchem-1645	307	13	l	l	NOUN
eurjchem-1645	307	14	)	)	PUNCT
eurjchem-1645	307	15	to	to	ADP
eurjchem-1645	307	16	a	a	DET
eurjchem-1645	307	17	stirred	stir	VERB
eurjchem-1645	307	18	solution	solution	NOUN
eurjchem-1645	307	19	of	of	ADP
eurjchem-1645	307	20	compounds	compound	NOUN
eurjchem-1645	307	21	12a‐h	12a‐h	NOUN
eurjchem-1645	307	22	(	(	PUNCT
eurjchem-1645	307	23	1	1	NUM
eurjchem-1645	307	24	mmol	mmol	NOUN
eurjchem-1645	307	25	)	)	PUNCT
eurjchem-1645	307	26	was	be	AUX
eurjchem-1645	307	27	dissolved	dissolve	VERB
eurjchem-1645	307	28	in	in	ADP
eurjchem-1645	307	29	2	2	NUM
eurjchem-1645	307	30	n	n	PRON
eurjchem-1645	307	31	dioxane	dioxane	NOUN
eurjchem-1645	307	32	in	in	ADP
eurjchem-1645	307	33	hcl	hcl	PROPN
eurjchem-1645	307	34	(	(	PUNCT
eurjchem-1645	307	35	10	10	NUM
eurjchem-1645	307	36	ml	ml	NOUN
eurjchem-1645	307	37	)	)	PUNCT
eurjchem-1645	307	38	and	and	CCONJ
eurjchem-1645	307	39	stirred	stir	VERB
eurjchem-1645	307	40	reaction	reaction	NOUN
eurjchem-1645	307	41	mixture	mixture	NOUN
eurjchem-1645	307	42	to	to	PART
eurjchem-1645	307	43	room	room	VERB
eurjchem-1645	307	44	temperature	temperature	NOUN
eurjchem-1645	307	45	for	for	ADP
eurjchem-1645	307	46	6	6	NUM
eurjchem-1645	307	47	h.	h.	NOUN
eurjchem-1645	307	48	progress	progress	NOUN
eurjchem-1645	307	49	of	of	ADP
eurjchem-1645	307	50	reaction	reaction	NOUN
eurjchem-1645	307	51	was	be	AUX
eurjchem-1645	307	52	monitored	monitor	VERB
eurjchem-1645	307	53	by	by	ADP
eurjchem-1645	307	54	lc‐ms	lc‐ms	PRON
eurjchem-1645	307	55	for	for	ADP
eurjchem-1645	307	56	the	the	DET
eurjchem-1645	307	57	consumption	consumption	NOUN
eurjchem-1645	307	58	of	of	ADP
eurjchem-1645	307	59	starting	start	VERB
eurjchem-1645	307	60	material	material	NOUN
eurjchem-1645	307	61	.	.	PUNCT
eurjchem-1645	308	1	after	after	ADP
eurjchem-1645	308	2	completion	completion	NOUN
eurjchem-1645	308	3	the	the	DET
eurjchem-1645	308	4	reaction	reaction	NOUN
eurjchem-1645	308	5	,	,	PUNCT
eurjchem-1645	308	6	the	the	DET
eurjchem-1645	308	7	reaction	reaction	NOUN
eurjchem-1645	308	8	mixture	mixture	NOUN
eurjchem-1645	308	9	evaporated	evaporate	VERB
eurjchem-1645	308	10	under	under	ADP
eurjchem-1645	308	11	reduced	reduced	ADJ
eurjchem-1645	308	12	pressure	pressure	NOUN
eurjchem-1645	308	13	to	to	PART
eurjchem-1645	308	14	obtain	obtain	VERB
eurjchem-1645	308	15	yellow	yellow	ADJ
eurjchem-1645	308	16	gummy	gummy	ADJ
eurjchem-1645	308	17	material	material	NOUN
eurjchem-1645	308	18	.	.	PUNCT
eurjchem-1645	309	1	the	the	DET
eurjchem-1645	309	2	crude	crude	NOUN
eurjchem-1645	309	3	obtained	obtain	VERB
eurjchem-1645	309	4	was	be	AUX
eurjchem-1645	309	5	washed	wash	VERB
eurjchem-1645	309	6	with	with	ADP
eurjchem-1645	309	7	10	10	NUM
eurjchem-1645	309	8	%	%	NOUN
eurjchem-1645	309	9	ethyl	ethyl	PROPN
eurjchem-1645	309	10	acetate	acetate	NOUN
eurjchem-1645	309	11	:	:	PUNCT
eurjchem-1645	309	12	hexane	hexane	NOUN
eurjchem-1645	309	13	,	,	PUNCT
eurjchem-1645	309	14	hexane	hexane	NOUN
eurjchem-1645	309	15	and	and	CCONJ
eurjchem-1645	309	16	diethyl	diethyl	NOUN
eurjchem-1645	309	17	ether	ether	NOUN
eurjchem-1645	309	18	to	to	PART
eurjchem-1645	309	19	obtain	obtain	VERB
eurjchem-1645	309	20	crude	crude	ADJ
eurjchem-1645	309	21	13a‐h	13a‐h	NOUN
eurjchem-1645	309	22	as	as	ADP
eurjchem-1645	309	23	yellow	yellow	ADJ
eurjchem-1645	309	24	solid	solid	ADJ
eurjchem-1645	309	25	material	material	NOUN
eurjchem-1645	309	26	.	.	PUNCT
eurjchem-1645	310	1	the	the	DET
eurjchem-1645	310	2	crude	crude	NOUN
eurjchem-1645	310	3	was	be	AUX
eurjchem-1645	310	4	purified	purify	VERB
eurjchem-1645	310	5	by	by	ADP
eurjchem-1645	310	6	column	column	NOUN
eurjchem-1645	310	7	chromatography	chromatography	NOUN
eurjchem-1645	310	8	(	(	PUNCT
eurjchem-1645	310	9	silica	silica	NOUN
eurjchem-1645	310	10	gel	gel	NOUN
eurjchem-1645	310	11	,	,	PUNCT
eurjchem-1645	310	12	230‐400	230‐400	PROPN
eurjchem-1645	310	13	mesh	mesh	NOUN
eurjchem-1645	310	14	)	)	PUNCT
eurjchem-1645	310	15	by	by	ADP
eurjchem-1645	310	16	using	use	VERB
eurjchem-1645	310	17	25‐75	25‐75	NUM
eurjchem-1645	310	18	%	%	NOUN
eurjchem-1645	310	19	ethyl	ethyl	PROPN
eurjchem-1645	310	20	acetate	acetate	NOUN
eurjchem-1645	310	21	and	and	CCONJ
eurjchem-1645	310	22	hexane	hexane	NOUN
eurjchem-1645	310	23	to	to	PART
eurjchem-1645	310	24	obtain	obtain	VERB
eurjchem-1645	310	25	desired	desire	VERB
eurjchem-1645	310	26	compounds	compound	NOUN
eurjchem-1645	310	27	13a‐h	13a‐h	ADJ
eurjchem-1645	310	28	as	as	ADP
eurjchem-1645	310	29	solid	solid	ADJ
eurjchem-1645	310	30	materials	material	NOUN
eurjchem-1645	310	31	.	.	PUNCT
eurjchem-1645	311	1	3‐(benzofuran‐2‐yl)‐4	3‐(benzofuran‐2‐yl)‐4	NUM
eurjchem-1645	311	2	,	,	PUNCT
eurjchem-1645	311	3	5	5	NUM
eurjchem-1645	311	4	,	,	PUNCT
eurjchem-1645	311	5	6	6	NUM
eurjchem-1645	311	6	,	,	PUNCT
eurjchem-1645	311	7	7‐tetrahydro‐6‐(3‐methoxyphen	7‐tetrahydro‐6‐(3‐methoxyphen	ADJ
eurjchem-1645	311	8	yl)‐1h‐pyrazolo[3,4‐c]pyridine	yl)‐1h‐pyrazolo[3,4‐c]pyridine	PROPN
eurjchem-1645	311	9	(	(	PUNCT
eurjchem-1645	311	10	13a	13a	NOUN
eurjchem-1645	311	11	):	):	PUNCT
eurjchem-1645	311	12	color	color	NOUN
eurjchem-1645	311	13	:	:	PUNCT
eurjchem-1645	311	14	white	white	ADJ
eurjchem-1645	311	15	.	.	PUNCT
eurjchem-1645	312	1	yield	yield	NOUN
eurjchem-1645	312	2	:	:	PUNCT
eurjchem-1645	312	3	91	91	NUM
eurjchem-1645	312	4	%	%	NOUN
eurjchem-1645	312	5	.	.	PUNCT
eurjchem-1645	313	1	m.p	m.p	PROPN
eurjchem-1645	313	2	.	.	PROPN
eurjchem-1645	313	3	:	:	PUNCT
eurjchem-1645	314	1	155‐156	155‐156	NUM
eurjchem-1645	314	2	°	°	PROPN
eurjchem-1645	314	3	c	c	X
eurjchem-1645	314	4	.	.	PUNCT
eurjchem-1645	314	5	1h	1h	NUM
eurjchem-1645	314	6	nmr	nmr	NOUN
eurjchem-1645	314	7	(	(	PUNCT
eurjchem-1645	314	8	400	400	NUM
eurjchem-1645	314	9	mhz	mhz	NOUN
eurjchem-1645	314	10	,	,	PUNCT
eurjchem-1645	314	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	314	12	,	,	PUNCT
eurjchem-1645	314	13	δ	δ	PROPN
eurjchem-1645	314	14	,	,	PUNCT
eurjchem-1645	314	15	ppm	ppm	NOUN
eurjchem-1645	314	16	):	):	PUNCT
eurjchem-1645	314	17	2.84	2.84	NUM
eurjchem-1645	314	18	(	(	PUNCT
eurjchem-1645	314	19	d	d	PROPN
eurjchem-1645	314	20	,	,	PUNCT
eurjchem-1645	314	21	2h	2h	NUM
eurjchem-1645	314	22	,	,	PUNCT
eurjchem-1645	314	23	j	j	PROPN
eurjchem-1645	314	24	=	=	SYM
eurjchem-1645	314	25	8	8	NUM
eurjchem-1645	314	26	hz	hz	NOUN
eurjchem-1645	314	27	,	,	PUNCT
eurjchem-1645	314	28	ch2	ch2	PROPN
eurjchem-1645	314	29	)	)	PUNCT
eurjchem-1645	314	30	,	,	PUNCT
eurjchem-1645	314	31	3.62	3.62	NUM
eurjchem-1645	314	32	(	(	PUNCT
eurjchem-1645	314	33	s	s	PROPN
eurjchem-1645	314	34	,	,	PUNCT
eurjchem-1645	314	35	2h	2h	NUM
eurjchem-1645	314	36	,	,	PUNCT
eurjchem-1645	314	37	ch2	ch2	PROPN
eurjchem-1645	314	38	)	)	PUNCT
eurjchem-1645	314	39	,	,	PUNCT
eurjchem-1645	314	40	3.78	3.78	NUM
eurjchem-1645	314	41	(	(	PUNCT
eurjchem-1645	314	42	s	s	PROPN
eurjchem-1645	314	43	,	,	PUNCT
eurjchem-1645	314	44	3h	3h	NUM
eurjchem-1645	314	45	,	,	PUNCT
eurjchem-1645	314	46	o‐ch3	o‐ch3	PROPN
eurjchem-1645	314	47	)	)	PUNCT
eurjchem-1645	314	48	,	,	PUNCT
eurjchem-1645	314	49	4.39	4.39	NUM
eurjchem-1645	314	50	(	(	PUNCT
eurjchem-1645	314	51	d	d	NOUN
eurjchem-1645	314	52	,	,	PUNCT
eurjchem-1645	314	53	2h	2h	NUM
eurjchem-1645	314	54	,	,	PUNCT
eurjchem-1645	314	55	j	j	PROPN
eurjchem-1645	314	56	=	=	SYM
eurjchem-1645	314	57	7.8	7.8	NUM
eurjchem-1645	314	58	hz	hz	NOUN
eurjchem-1645	314	59	,	,	PUNCT
eurjchem-1645	314	60	n‐ch2	n‐ch2	PROPN
eurjchem-1645	314	61	)	)	PUNCT
eurjchem-1645	314	62	,	,	PUNCT
eurjchem-1645	314	63	6.96	6.96	NUM
eurjchem-1645	314	64	(	(	PUNCT
eurjchem-1645	314	65	d	d	PROPN
eurjchem-1645	314	66	,	,	PUNCT
eurjchem-1645	314	67	1h	1h	NUM
eurjchem-1645	314	68	,	,	PUNCT
eurjchem-1645	314	69	j	j	PROPN
eurjchem-1645	314	70	=	=	SYM
eurjchem-1645	314	71	7.8	7.8	NUM
eurjchem-1645	314	72	hz	hz	NOUN
eurjchem-1645	314	73	,	,	PUNCT
eurjchem-1645	314	74	ar‐h	ar‐h	PROPN
eurjchem-1645	314	75	)	)	PUNCT
eurjchem-1645	314	76	,	,	PUNCT
eurjchem-1645	314	77	7.2‐7.12	7.2‐7.12	NUM
eurjchem-1645	314	78	(	(	PUNCT
eurjchem-1645	314	79	m	m	PROPN
eurjchem-1645	314	80	,	,	PUNCT
eurjchem-1645	314	81	2h	2h	NUM
eurjchem-1645	314	82	,	,	PUNCT
eurjchem-1645	314	83	ar‐h	ar‐h	NOUN
eurjchem-1645	314	84	)	)	PUNCT
eurjchem-1645	314	85	,	,	PUNCT
eurjchem-1645	314	86	7.36‐7.21	7.36‐7.21	PROPN
eurjchem-1645	314	87	(	(	PUNCT
eurjchem-1645	314	88	m	m	PROPN
eurjchem-1645	314	89	,	,	PUNCT
eurjchem-1645	314	90	3h	3h	NUM
eurjchem-1645	314	91	,	,	PUNCT
eurjchem-1645	314	92	ar‐h	ar‐h	NOUN
eurjchem-1645	314	93	)	)	PUNCT
eurjchem-1645	314	94	,	,	PUNCT
eurjchem-1645	314	95	7.46	7.46	NUM
eurjchem-1645	314	96	(	(	PUNCT
eurjchem-1645	314	97	t	t	PROPN
eurjchem-1645	314	98	,	,	PUNCT
eurjchem-1645	314	99	1h	1h	NUM
eurjchem-1645	314	100	,	,	PUNCT
eurjchem-1645	314	101	j	j	PROPN
eurjchem-1645	315	1	=	=	SYM
eurjchem-1645	315	2	7.6	7.6	NUM
eurjchem-1645	315	3	hz	hz	NOUN
eurjchem-1645	315	4	,	,	PUNCT
eurjchem-1645	315	5	ar‐h	ar‐h	NOUN
eurjchem-1645	315	6	)	)	PUNCT
eurjchem-1645	315	7	,	,	PUNCT
eurjchem-1645	315	8	7.74‐7.63	7.74‐7.63	NUM
eurjchem-1645	315	9	(	(	PUNCT
eurjchem-1645	315	10	m	m	PROPN
eurjchem-1645	315	11	,	,	PUNCT
eurjchem-1645	315	12	2h	2h	NUM
eurjchem-1645	315	13	,	,	PUNCT
eurjchem-1645	315	14	ar‐h	ar‐h	NOUN
eurjchem-1645	315	15	)	)	PUNCT
eurjchem-1645	315	16	,	,	PUNCT
eurjchem-1645	315	17	13.38	13.38	NUM
eurjchem-1645	315	18	(	(	PUNCT
eurjchem-1645	315	19	s	s	PROPN
eurjchem-1645	315	20	,	,	PUNCT
eurjchem-1645	315	21	1h	1h	NUM
eurjchem-1645	315	22	,	,	PUNCT
eurjchem-1645	315	23	nh	nh	PROPN
eurjchem-1645	315	24	)	)	PUNCT
eurjchem-1645	315	25	.	.	PUNCT
eurjchem-1645	316	1	13c	13c	NOUN
eurjchem-1645	316	2	nmr	nmr	NOUN
eurjchem-1645	316	3	(	(	PUNCT
eurjchem-1645	316	4	100	100	NUM
eurjchem-1645	316	5	mhz	mhz	NOUN
eurjchem-1645	316	6	,	,	PUNCT
eurjchem-1645	316	7	cdcl3	cdcl3	PROPN
eurjchem-1645	316	8	,	,	PUNCT
eurjchem-1645	316	9	δ	δ	PROPN
eurjchem-1645	316	10	,	,	PUNCT
eurjchem-1645	316	11	ppm	ppm	NOUN
eurjchem-1645	316	12	):	):	PUNCT
eurjchem-1645	316	13	10.34	10.34	NUM
eurjchem-1645	316	14	,	,	PUNCT
eurjchem-1645	316	15	48.55	48.55	NUM
eurjchem-1645	316	16	,	,	PUNCT
eurjchem-1645	316	17	51.72	51.72	NUM
eurjchem-1645	316	18	,	,	PUNCT
eurjchem-1645	316	19	55.85	55.85	NUM
eurjchem-1645	316	20	,	,	PUNCT
eurjchem-1645	316	21	97.56	97.56	NUM
eurjchem-1645	316	22	,	,	PUNCT
eurjchem-1645	316	23	103.11	103.11	NUM
eurjchem-1645	316	24	,	,	PUNCT
eurjchem-1645	316	25	103.21	103.21	NUM
eurjchem-1645	316	26	,	,	PUNCT
eurjchem-1645	316	27	106.81	106.81	NUM
eurjchem-1645	316	28	,	,	PUNCT
eurjchem-1645	316	29	111.12	111.12	NUM
eurjchem-1645	316	30	,	,	PUNCT
eurjchem-1645	316	31	121.18	121.18	NUM
eurjchem-1645	316	32	,	,	PUNCT
eurjchem-1645	316	33	122.34	122.34	NUM
eurjchem-1645	316	34	,	,	PUNCT
eurjchem-1645	316	35	123.76	123.76	NUM
eurjchem-1645	316	36	,	,	PUNCT
eurjchem-1645	316	37	124.44	124.44	NUM
eurjchem-1645	316	38	,	,	PUNCT
eurjchem-1645	316	39	130.84	130.84	NUM
eurjchem-1645	316	40	,	,	PUNCT
eurjchem-1645	316	41	135.67	135.67	NUM
eurjchem-1645	316	42	,	,	PUNCT
eurjchem-1645	316	43	150.42	150.42	NUM
eurjchem-1645	316	44	,	,	PUNCT
eurjchem-1645	316	45	150.67	150.67	NUM
eurjchem-1645	316	46	,	,	PUNCT
eurjchem-1645	316	47	155.67	155.67	NUM
eurjchem-1645	316	48	,	,	PUNCT
eurjchem-1645	316	49	161.82	161.82	NUM
eurjchem-1645	316	50	.	.	PUNCT
eurjchem-1645	317	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	317	2	(	(	PUNCT
eurjchem-1645	317	3	ei	ei	PROPN
eurjchem-1645	317	4	,	,	PUNCT
eurjchem-1645	317	5	m	m	PROPN
eurjchem-1645	317	6	/	/	SYM
eurjchem-1645	317	7	z	z	NOUN
eurjchem-1645	317	8	):	):	PUNCT
eurjchem-1645	317	9	345	345	NUM
eurjchem-1645	317	10	(	(	PUNCT
eurjchem-1645	317	11	m+h	m+h	NOUN
eurjchem-1645	317	12	)	)	PUNCT
eurjchem-1645	317	13	.	.	PUNCT
eurjchem-1645	318	1	anal	anal	PROPN
eurjchem-1645	318	2	.	.	PUNCT
eurjchem-1645	318	3	calcd	calcd	NOUN
eurjchem-1645	318	4	.	.	PUNCT
eurjchem-1645	319	1	for	for	SCONJ
eurjchem-1645	319	2	c21h19n3o2	c21h19n3o2	PROPN
eurjchem-1645	319	3	:	:	PUNCT
eurjchem-1645	319	4	c	c	NOUN
eurjchem-1645	319	5	,	,	PUNCT
eurjchem-1645	319	6	73.03	73.03	NUM
eurjchem-1645	319	7	;	;	PUNCT
eurjchem-1645	319	8	h	h	NOUN
eurjchem-1645	319	9	,	,	PUNCT
eurjchem-1645	319	10	5.54	5.54	NUM
eurjchem-1645	319	11	;	;	PUNCT
eurjchem-1645	319	12	n	n	CCONJ
eurjchem-1645	319	13	,	,	PUNCT
eurjchem-1645	319	14	12.17	12.17	NUM
eurjchem-1645	319	15	.	.	PUNCT
eurjchem-1645	319	16	found	find	VERB
eurjchem-1645	319	17	:	:	PUNCT
eurjchem-1645	320	1	c	c	X
eurjchem-1645	320	2	,	,	PUNCT
eurjchem-1645	320	3	73.05	73.05	NUM
eurjchem-1645	320	4	;	;	PUNCT
eurjchem-1645	320	5	h	h	NOUN
eurjchem-1645	320	6	,	,	PUNCT
eurjchem-1645	320	7	5.53	5.53	NUM
eurjchem-1645	320	8	;	;	PUNCT
eurjchem-1645	320	9	n	n	CCONJ
eurjchem-1645	320	10	,	,	PUNCT
eurjchem-1645	320	11	12.15	12.15	NUM
eurjchem-1645	320	12	%	%	NOUN
eurjchem-1645	320	13	.	.	PUNCT
eurjchem-1645	321	1	hplc	hplc	NOUN
eurjchem-1645	321	2	:	:	PUNCT
eurjchem-1645	321	3	r.t	r.t	PROPN
eurjchem-1645	321	4	.	.	PUNCT
eurjchem-1645	322	1	=	=	NOUN
eurjchem-1645	322	2	5.68	5.68	NUM
eurjchem-1645	322	3	min	min	NOUN
eurjchem-1645	322	4	,	,	PUNCT
eurjchem-1645	322	5	purity	purity	NOUN
eurjchem-1645	322	6	=	=	PUNCT
eurjchem-1645	322	7	98.3	98.3	NUM
eurjchem-1645	322	8	%	%	NOUN
eurjchem-1645	322	9	.	.	PUNCT
eurjchem-1645	323	1	3‐(benzo[b]thiophen‐2‐yl)‐4,5	3‐(benzo[b]thiophen‐2‐yl)‐4,5	NUM
eurjchem-1645	323	2	,	,	PUNCT
eurjchem-1645	323	3	6	6	NUM
eurjchem-1645	323	4	,	,	PUNCT
eurjchem-1645	323	5	7‐tetrahydro‐6‐(3‐methoxy	7‐tetrahydro‐6‐(3‐methoxy	NUM
eurjchem-1645	323	6	phenyl)‐1h‐pyrazolo[3,4‐c]pyridine	phenyl)‐1h‐pyrazolo[3,4‐c]pyridine	PROPN
eurjchem-1645	323	7	(	(	PUNCT
eurjchem-1645	323	8	13b	13b	NUM
eurjchem-1645	323	9	):	):	PUNCT
eurjchem-1645	323	10	color	color	NOUN
eurjchem-1645	323	11	:	:	PUNCT
eurjchem-1645	323	12	yellow	yellow	ADJ
eurjchem-1645	323	13	.	.	PUNCT
eurjchem-1645	324	1	yield	yield	NOUN
eurjchem-1645	324	2	:	:	PUNCT
eurjchem-1645	324	3	89	89	NUM
eurjchem-1645	324	4	%	%	NOUN
eurjchem-1645	324	5	.	.	PUNCT
eurjchem-1645	325	1	m.p	m.p	PROPN
eurjchem-1645	325	2	.	.	PROPN
eurjchem-1645	325	3	:	:	PUNCT
eurjchem-1645	326	1	161‐162	161‐162	NUM
eurjchem-1645	326	2	°	°	SYM
eurjchem-1645	326	3	c	c	X
eurjchem-1645	326	4	.	.	PUNCT
eurjchem-1645	327	1	1h	1h	NUM
eurjchem-1645	327	2	nmr	nmr	NOUN
eurjchem-1645	327	3	(	(	PUNCT
eurjchem-1645	327	4	400	400	NUM
eurjchem-1645	327	5	mhz	mhz	NOUN
eurjchem-1645	327	6	,	,	PUNCT
eurjchem-1645	327	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	327	8	,	,	PUNCT
eurjchem-1645	327	9	δ	δ	PROPN
eurjchem-1645	327	10	,	,	PUNCT
eurjchem-1645	327	11	ppm	ppm	NUM
eurjchem-1645	327	12	):	):	PUNCT
eurjchem-1645	327	13	2.97‐2.81	2.97‐2.81	NUM
eurjchem-1645	327	14	(	(	PUNCT
eurjchem-1645	327	15	m	m	PROPN
eurjchem-1645	327	16	,	,	PUNCT
eurjchem-1645	327	17	2h	2h	NUM
eurjchem-1645	327	18	,	,	PUNCT
eurjchem-1645	327	19	ch2	ch2	PROPN
eurjchem-1645	327	20	)	)	PUNCT
eurjchem-1645	327	21	,	,	PUNCT
eurjchem-1645	327	22	3.63	3.63	NUM
eurjchem-1645	327	23	(	(	PUNCT
eurjchem-1645	327	24	s	s	PROPN
eurjchem-1645	327	25	,	,	PUNCT
eurjchem-1645	327	26	2h	2h	NUM
eurjchem-1645	327	27	,	,	PUNCT
eurjchem-1645	327	28	ch2	ch2	PROPN
eurjchem-1645	327	29	)	)	PUNCT
eurjchem-1645	327	30	,	,	PUNCT
eurjchem-1645	327	31	3.76	3.76	NUM
eurjchem-1645	327	32	(	(	PUNCT
eurjchem-1645	327	33	s	s	PROPN
eurjchem-1645	327	34	,	,	PUNCT
eurjchem-1645	327	35	3h	3h	NUM
eurjchem-1645	327	36	,	,	PUNCT
eurjchem-1645	327	37	o‐ch3	o‐ch3	PROPN
eurjchem-1645	327	38	)	)	PUNCT
eurjchem-1645	327	39	,	,	PUNCT
eurjchem-1645	327	40	4.36	4.36	NUM
eurjchem-1645	327	41	(	(	PUNCT
eurjchem-1645	327	42	d	d	PROPN
eurjchem-1645	327	43	,	,	PUNCT
eurjchem-1645	327	44	2h	2h	NUM
eurjchem-1645	327	45	,	,	PUNCT
eurjchem-1645	327	46	j	j	PROPN
eurjchem-1645	327	47	=	=	PROPN
eurjchem-1645	327	48	8.4	8.4	NUM
eurjchem-1645	327	49	hz	hz	NOUN
eurjchem-1645	327	50	,	,	PUNCT
eurjchem-1645	327	51	n‐ch2	n‐ch2	PROPN
eurjchem-1645	327	52	)	)	PUNCT
eurjchem-1645	327	53	,	,	PUNCT
eurjchem-1645	327	54	6.38	6.38	NUM
eurjchem-1645	327	55	(	(	PUNCT
eurjchem-1645	327	56	t	t	PROPN
eurjchem-1645	327	57	,	,	PUNCT
eurjchem-1645	327	58	1h	1h	NUM
eurjchem-1645	327	59	,	,	PUNCT
eurjchem-1645	327	60	j	j	PROPN
eurjchem-1645	327	61	=	=	SYM
eurjchem-1645	327	62	7.6	7.6	NUM
eurjchem-1645	327	63	hz	hz	NOUN
eurjchem-1645	327	64	,	,	PUNCT
eurjchem-1645	327	65	ar‐h	ar‐h	NOUN
eurjchem-1645	327	66	)	)	PUNCT
eurjchem-1645	327	67	,	,	PUNCT
eurjchem-1645	327	68	6.55	6.55	NUM
eurjchem-1645	327	69	(	(	PUNCT
eurjchem-1645	327	70	s	s	PROPN
eurjchem-1645	327	71	,	,	PUNCT
eurjchem-1645	327	72	1h	1h	NUM
eurjchem-1645	327	73	,	,	PUNCT
eurjchem-1645	327	74	ar‐h	ar‐h	NOUN
eurjchem-1645	327	75	)	)	PUNCT
eurjchem-1645	327	76	,	,	PUNCT
eurjchem-1645	327	77	6.63	6.63	NUM
eurjchem-1645	327	78	(	(	PUNCT
eurjchem-1645	327	79	m	m	PROPN
eurjchem-1645	327	80	,	,	PUNCT
eurjchem-1645	327	81	1h	1h	NUM
eurjchem-1645	327	82	,	,	PUNCT
eurjchem-1645	327	83	ar‐h	ar‐h	NOUN
eurjchem-1645	327	84	)	)	PUNCT
eurjchem-1645	327	85	,	,	PUNCT
eurjchem-1645	327	86	7.18‐7.04	7.18‐7.04	NUM
eurjchem-1645	327	87	(	(	PUNCT
eurjchem-1645	327	88	m	m	PROPN
eurjchem-1645	327	89	,	,	PUNCT
eurjchem-1645	327	90	2h	2h	NUM
eurjchem-1645	327	91	,	,	PUNCT
eurjchem-1645	327	92	ar‐h	ar‐h	NOUN
eurjchem-1645	327	93	)	)	PUNCT
eurjchem-1645	327	94	,	,	PUNCT
eurjchem-1645	327	95	7.32‐7.2	7.32‐7.2	NUM
eurjchem-1645	327	96	(	(	PUNCT
eurjchem-1645	327	97	m	m	PROPN
eurjchem-1645	327	98	,	,	PUNCT
eurjchem-1645	327	99	2h	2h	NUM
eurjchem-1645	327	100	,	,	PUNCT
eurjchem-1645	327	101	ar‐h	ar‐h	NOUN
eurjchem-1645	327	102	)	)	PUNCT
eurjchem-1645	327	103	,	,	PUNCT
eurjchem-1645	327	104	7.73‐7.68	7.73‐7.68	PROPN
eurjchem-1645	327	105	(	(	PUNCT
eurjchem-1645	327	106	m	m	PROPN
eurjchem-1645	327	107	,	,	PUNCT
eurjchem-1645	327	108	2h	2h	NUM
eurjchem-1645	327	109	,	,	PUNCT
eurjchem-1645	327	110	ar‐h	ar‐h	NOUN
eurjchem-1645	327	111	)	)	PUNCT
eurjchem-1645	327	112	,	,	PUNCT
eurjchem-1645	327	113	13.4	13.4	NUM
eurjchem-1645	327	114	(	(	PUNCT
eurjchem-1645	327	115	s	s	PROPN
eurjchem-1645	327	116	,	,	PUNCT
eurjchem-1645	327	117	1h	1h	NUM
eurjchem-1645	327	118	,	,	PUNCT
eurjchem-1645	327	119	nh	nh	PROPN
eurjchem-1645	327	120	)	)	PUNCT
eurjchem-1645	327	121	.	.	PUNCT
eurjchem-1645	328	1	13c	13c	NOUN
eurjchem-1645	328	2	nmr	nmr	NOUN
eurjchem-1645	328	3	(	(	PUNCT
eurjchem-1645	328	4	100	100	NUM
eurjchem-1645	328	5	mhz	mhz	NOUN
eurjchem-1645	328	6	,	,	PUNCT
eurjchem-1645	328	7	cdcl3	cdcl3	PROPN
eurjchem-1645	328	8	,	,	PUNCT
eurjchem-1645	328	9	δ	δ	PROPN
eurjchem-1645	328	10	,	,	PUNCT
eurjchem-1645	328	11	ppm	ppm	NOUN
eurjchem-1645	328	12	):	):	PUNCT
eurjchem-1645	328	13	10.24	10.24	NUM
eurjchem-1645	328	14	,	,	PUNCT
eurjchem-1645	328	15	48.45	48.45	NUM
eurjchem-1645	328	16	,	,	PUNCT
eurjchem-1645	328	17	51.62	51.62	NUM
eurjchem-1645	328	18	,	,	PUNCT
eurjchem-1645	328	19	55.85	55.85	NUM
eurjchem-1645	328	20	,	,	PUNCT
eurjchem-1645	328	21	97.66	97.66	NUM
eurjchem-1645	328	22	,	,	PUNCT
eurjchem-1645	328	23	102.11	102.11	NUM
eurjchem-1645	328	24	,	,	PUNCT
eurjchem-1645	328	25	102.21	102.21	NUM
eurjchem-1645	328	26	,	,	PUNCT
eurjchem-1645	328	27	106.81	106.81	NUM
eurjchem-1645	328	28	,	,	PUNCT
eurjchem-1645	328	29	111.2	111.2	NUM
eurjchem-1645	328	30	,	,	PUNCT
eurjchem-1645	328	31	120.18	120.18	NUM
eurjchem-1645	328	32	,	,	PUNCT
eurjchem-1645	328	33	122.34	122.34	NUM
eurjchem-1645	328	34	,	,	PUNCT
eurjchem-1645	328	35	123.66	123.66	NUM
eurjchem-1645	328	36	,	,	PUNCT
eurjchem-1645	328	37	124.44	124.44	NUM
eurjchem-1645	328	38	,	,	PUNCT
eurjchem-1645	328	39	130.84	130.84	NUM
eurjchem-1645	328	40	,	,	PUNCT
eurjchem-1645	328	41	135.66	135.66	NUM
eurjchem-1645	328	42	,	,	PUNCT
eurjchem-1645	328	43	150.32	150.32	NUM
eurjchem-1645	328	44	,	,	PUNCT
eurjchem-1645	328	45	150.67	150.67	NUM
eurjchem-1645	328	46	,	,	PUNCT
eurjchem-1645	328	47	154.67	154.67	NUM
eurjchem-1645	328	48	,	,	PUNCT
eurjchem-1645	328	49	161.72	161.72	NUM
eurjchem-1645	328	50	.	.	PUNCT
eurjchem-1645	329	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	329	2	(	(	PUNCT
eurjchem-1645	329	3	ei	ei	PROPN
eurjchem-1645	329	4	,	,	PUNCT
eurjchem-1645	329	5	m	m	PROPN
eurjchem-1645	329	6	/	/	SYM
eurjchem-1645	329	7	z	z	NOUN
eurjchem-1645	329	8	):	):	PUNCT
eurjchem-1645	329	9	361	361	NUM
eurjchem-1645	329	10	(	(	PUNCT
eurjchem-1645	329	11	m+h	m+h	NOUN
eurjchem-1645	329	12	)	)	PUNCT
eurjchem-1645	329	13	.	.	PUNCT
eurjchem-1645	330	1	anal	anal	PROPN
eurjchem-1645	330	2	.	.	PUNCT
eurjchem-1645	330	3	calcd	calcd	NOUN
eurjchem-1645	330	4	.	.	PUNCT
eurjchem-1645	331	1	for	for	SCONJ
eurjchem-1645	331	2	c21h19n3os	c21h19n3os	PROPN
eurjchem-1645	331	3	:	:	PUNCT
eurjchem-1645	331	4	c	c	X
eurjchem-1645	331	5	,	,	PUNCT
eurjchem-1645	331	6	69.78	69.78	NUM
eurjchem-1645	331	7	;	;	PUNCT
eurjchem-1645	331	8	h	h	NOUN
eurjchem-1645	331	9	,	,	PUNCT
eurjchem-1645	331	10	5.30	5.30	NUM
eurjchem-1645	331	11	;	;	PUNCT
eurjchem-1645	331	12	n	n	CCONJ
eurjchem-1645	331	13	,	,	PUNCT
eurjchem-1645	331	14	11.63	11.63	NUM
eurjchem-1645	331	15	.	.	PUNCT
eurjchem-1645	331	16	found	find	VERB
eurjchem-1645	331	17	:	:	PUNCT
eurjchem-1645	332	1	c	c	X
eurjchem-1645	332	2	,	,	PUNCT
eurjchem-1645	332	3	69.77	69.77	NUM
eurjchem-1645	332	4	;	;	PUNCT
eurjchem-1645	332	5	h	h	NOUN
eurjchem-1645	332	6	,	,	PUNCT
eurjchem-1645	332	7	5.32	5.32	NUM
eurjchem-1645	332	8	;	;	PUNCT
eurjchem-1645	332	9	n	n	CCONJ
eurjchem-1645	332	10	,	,	PUNCT
eurjchem-1645	332	11	11.61	11.61	NUM
eurjchem-1645	332	12	%	%	NOUN
eurjchem-1645	332	13	.	.	PUNCT
eurjchem-1645	333	1	hplc	hplc	NOUN
eurjchem-1645	333	2	:	:	PUNCT
eurjchem-1645	333	3	r.t	r.t	PROPN
eurjchem-1645	333	4	.	.	PUNCT
eurjchem-1645	333	5	=	=	NOUN
eurjchem-1645	333	6	9.21	9.21	NUM
eurjchem-1645	333	7	min	min	NOUN
eurjchem-1645	333	8	,	,	PUNCT
eurjchem-1645	333	9	purity	purity	NOUN
eurjchem-1645	333	10	=	=	NOUN
eurjchem-1645	333	11	99.5	99.5	NUM
eurjchem-1645	333	12	%	%	NOUN
eurjchem-1645	333	13	.	.	PUNCT
eurjchem-1645	334	1	3‐(4	3‐(4	NUM
eurjchem-1645	334	2	,	,	PUNCT
eurjchem-1645	334	3	5	5	NUM
eurjchem-1645	334	4	,	,	PUNCT
eurjchem-1645	334	5	6,7‐tetrahydro‐6‐(3‐methoxyphenyl)‐1h‐pyrazolo[3	6,7‐tetrahydro‐6‐(3‐methoxyphenyl)‐1h‐pyrazolo[3	NUM
eurjchem-1645	334	6	,	,	PUNCT
eurjchem-1645	334	7	4‐c]pyridin‐3‐yl)quinolone	4‐c]pyridin‐3‐yl)quinolone	NUM
eurjchem-1645	334	8	(	(	PUNCT
eurjchem-1645	334	9	13c	13c	NOUN
eurjchem-1645	334	10	):	):	PUNCT
eurjchem-1645	334	11	color	color	NOUN
eurjchem-1645	334	12	:	:	PUNCT
eurjchem-1645	334	13	yellow	yellow	ADJ
eurjchem-1645	334	14	.	.	PUNCT
eurjchem-1645	335	1	yield	yield	NOUN
eurjchem-1645	335	2	:	:	PUNCT
eurjchem-1645	335	3	80	80	NUM
eurjchem-1645	335	4	%	%	NOUN
eurjchem-1645	335	5	.	.	PUNCT
eurjchem-1645	336	1	m.p	m.p	PROPN
eurjchem-1645	336	2	.	.	PROPN
eurjchem-1645	336	3	:	:	PUNCT
eurjchem-1645	337	1	179‐180	179‐180	NUM
eurjchem-1645	337	2	°	°	PROPN
eurjchem-1645	337	3	c	c	PROPN
eurjchem-1645	337	4	.	.	PUNCT
eurjchem-1645	338	1	1h	1h	NUM
eurjchem-1645	338	2	nmr	nmr	NOUN
eurjchem-1645	338	3	(	(	PUNCT
eurjchem-1645	338	4	400	400	NUM
eurjchem-1645	338	5	mhz	mhz	NOUN
eurjchem-1645	338	6	,	,	PUNCT
eurjchem-1645	338	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	338	8	,	,	PUNCT
eurjchem-1645	338	9	δ	δ	PROPN
eurjchem-1645	338	10	,	,	PUNCT
eurjchem-1645	338	11	ppm	ppm	NOUN
eurjchem-1645	338	12	):	):	PUNCT
eurjchem-1645	338	13	2.92	2.92	NUM
eurjchem-1645	338	14	(	(	PUNCT
eurjchem-1645	338	15	d	d	PROPN
eurjchem-1645	338	16	,	,	PUNCT
eurjchem-1645	338	17	2h	2h	NUM
eurjchem-1645	338	18	,	,	PUNCT
eurjchem-1645	338	19	j	j	PROPN
eurjchem-1645	338	20	=	=	PROPN
eurjchem-1645	338	21	8.2	8.2	NUM
eurjchem-1645	338	22	hz	hz	NOUN
eurjchem-1645	338	23	,	,	PUNCT
eurjchem-1645	338	24	ch2	ch2	PROPN
eurjchem-1645	338	25	)	)	PUNCT
eurjchem-1645	338	26	,	,	PUNCT
eurjchem-1645	338	27	3.61	3.61	NUM
eurjchem-1645	338	28	(	(	PUNCT
eurjchem-1645	338	29	t	t	PROPN
eurjchem-1645	338	30	,	,	PUNCT
eurjchem-1645	338	31	2h	2h	NUM
eurjchem-1645	338	32	,	,	PUNCT
eurjchem-1645	338	33	j	j	PROPN
eurjchem-1645	338	34	=	=	PROPN
eurjchem-1645	338	35	8.2	8.2	NUM
eurjchem-1645	338	36	hz	hz	NOUN
eurjchem-1645	338	37	,	,	PUNCT
eurjchem-1645	338	38	ch2	ch2	PROPN
eurjchem-1645	338	39	)	)	PUNCT
eurjchem-1645	338	40	,	,	PUNCT
eurjchem-1645	338	41	3.72	3.72	NUM
eurjchem-1645	338	42	(	(	PUNCT
eurjchem-1645	338	43	s	s	PROPN
eurjchem-1645	338	44	,	,	PUNCT
eurjchem-1645	338	45	3h	3h	NUM
eurjchem-1645	338	46	,	,	PUNCT
eurjchem-1645	338	47	o‐ch3	o‐ch3	PROPN
eurjchem-1645	338	48	)	)	PUNCT
eurjchem-1645	338	49	,	,	PUNCT
eurjchem-1645	338	50	4.42	4.42	NUM
eurjchem-1645	338	51	(	(	PUNCT
eurjchem-1645	338	52	s	s	PROPN
eurjchem-1645	338	53	,	,	PUNCT
eurjchem-1645	338	54	2h	2h	NUM
eurjchem-1645	338	55	,	,	PUNCT
eurjchem-1645	338	56	n‐ch2	n‐ch2	PROPN
eurjchem-1645	338	57	)	)	PUNCT
eurjchem-1645	338	58	,	,	PUNCT
eurjchem-1645	338	59	6.34	6.34	NUM
eurjchem-1645	338	60	(	(	PUNCT
eurjchem-1645	338	61	s	s	PROPN
eurjchem-1645	338	62	,	,	PUNCT
eurjchem-1645	338	63	1h	1h	NUM
eurjchem-1645	338	64	,	,	PUNCT
eurjchem-1645	338	65	ar‐h	ar‐h	NOUN
eurjchem-1645	338	66	)	)	PUNCT
eurjchem-1645	338	67	,	,	PUNCT
eurjchem-1645	338	68	6.56	6.56	NUM
eurjchem-1645	338	69	(	(	PUNCT
eurjchem-1645	338	70	s	s	PROPN
eurjchem-1645	338	71	,	,	PUNCT
eurjchem-1645	338	72	1h	1h	NUM
eurjchem-1645	338	73	,	,	PUNCT
eurjchem-1645	338	74	ar‐	ar‐	PROPN
eurjchem-1645	338	75	h	h	NOUN
eurjchem-1645	338	76	)	)	PUNCT
eurjchem-1645	338	77	,	,	PUNCT
eurjchem-1645	338	78	6.64	6.64	NUM
eurjchem-1645	338	79	(	(	PUNCT
eurjchem-1645	338	80	d	d	PROPN
eurjchem-1645	338	81	,	,	PUNCT
eurjchem-1645	338	82	1h	1h	NUM
eurjchem-1645	338	83	,	,	PUNCT
eurjchem-1645	338	84	j	j	PROPN
eurjchem-1645	338	85	=	=	SYM
eurjchem-1645	338	86	7.6	7.6	NUM
eurjchem-1645	338	87	hz	hz	NOUN
eurjchem-1645	338	88	,	,	PUNCT
eurjchem-1645	338	89	ar‐h	ar‐h	PROPN
eurjchem-1645	338	90	)	)	PUNCT
eurjchem-1645	338	91	,	,	PUNCT
eurjchem-1645	338	92	7.16	7.16	NUM
eurjchem-1645	338	93	(	(	PUNCT
eurjchem-1645	338	94	t	t	PROPN
eurjchem-1645	338	95	,	,	PUNCT
eurjchem-1645	338	96	1h	1h	NUM
eurjchem-1645	338	97	,	,	PUNCT
eurjchem-1645	338	98	j	j	PROPN
eurjchem-1645	338	99	=	=	SYM
eurjchem-1645	338	100	7.8	7.8	NUM
eurjchem-1645	338	101	hz	hz	NOUN
eurjchem-1645	338	102	,	,	PUNCT
eurjchem-1645	338	103	ar‐h	ar‐h	NOUN
eurjchem-1645	338	104	)	)	PUNCT
eurjchem-1645	338	105	,	,	PUNCT
eurjchem-1645	338	106	7.81‐7.59	7.81‐7.59	NUM
eurjchem-1645	338	107	(	(	PUNCT
eurjchem-1645	338	108	dd	dd	NOUN
eurjchem-1645	338	109	,	,	PUNCT
eurjchem-1645	338	110	2h	2h	NUM
eurjchem-1645	338	111	,	,	PUNCT
eurjchem-1645	338	112	j	j	PROPN
eurjchem-1645	338	113	=	=	PROPN
eurjchem-1645	338	114	8.4	8.4	NUM
eurjchem-1645	338	115	hz	hz	NOUN
eurjchem-1645	338	116	,	,	PUNCT
eurjchem-1645	338	117	16.8	16.8	NUM
eurjchem-1645	338	118	hz	hz	NOUN
eurjchem-1645	338	119	,	,	PUNCT
eurjchem-1645	338	120	ar‐h	ar‐h	PROPN
eurjchem-1645	338	121	)	)	PUNCT
eurjchem-1645	338	122	,	,	PUNCT
eurjchem-1645	338	123	8.08	8.08	NUM
eurjchem-1645	338	124	(	(	PUNCT
eurjchem-1645	338	125	t	t	PROPN
eurjchem-1645	338	126	,	,	PUNCT
eurjchem-1645	338	127	2h	2h	NUM
eurjchem-1645	338	128	,	,	PUNCT
eurjchem-1645	338	129	j	j	PROPN
eurjchem-1645	338	130	=	=	PROPN
eurjchem-1645	338	131	8.2	8.2	NUM
eurjchem-1645	338	132	hz	hz	ADJ
eurjchem-1645	338	133	,	,	PUNCT
eurjchem-1645	338	134	ar‐h	ar‐h	PROPN
eurjchem-1645	338	135	)	)	PUNCT
eurjchem-1645	338	136	,	,	PUNCT
eurjchem-1645	338	137	8.56	8.56	NUM
eurjchem-1645	338	138	(	(	PUNCT
eurjchem-1645	338	139	s	s	PROPN
eurjchem-1645	338	140	,	,	PUNCT
eurjchem-1645	338	141	1h	1h	NUM
eurjchem-1645	338	142	,	,	PUNCT
eurjchem-1645	338	143	ar‐h	ar‐h	NOUN
eurjchem-1645	338	144	)	)	PUNCT
eurjchem-1645	338	145	,	,	PUNCT
eurjchem-1645	338	146	9.38	9.38	NUM
eurjchem-1645	338	147	(	(	PUNCT
eurjchem-1645	338	148	s	s	PROPN
eurjchem-1645	338	149	,	,	PUNCT
eurjchem-1645	338	150	1h	1h	NUM
eurjchem-1645	338	151	,	,	PUNCT
eurjchem-1645	338	152	ar‐h	ar‐h	NOUN
eurjchem-1645	338	153	)	)	PUNCT
eurjchem-1645	338	154	,	,	PUNCT
eurjchem-1645	338	155	13.26	13.26	NUM
eurjchem-1645	338	156	(	(	PUNCT
eurjchem-1645	338	157	br	br	NOUN
eurjchem-1645	338	158	.	.	PUNCT
eurjchem-1645	339	1	s	s	PART
eurjchem-1645	339	2	,	,	PUNCT
eurjchem-1645	339	3	1h	1h	NUM
eurjchem-1645	339	4	,	,	PUNCT
eurjchem-1645	339	5	nh	nh	PROPN
eurjchem-1645	339	6	)	)	PUNCT
eurjchem-1645	339	7	.	.	PUNCT
eurjchem-1645	340	1	13c	13c	NOUN
eurjchem-1645	340	2	nmr	nmr	NOUN
eurjchem-1645	340	3	(	(	PUNCT
eurjchem-1645	340	4	100	100	NUM
eurjchem-1645	340	5	mhz	mhz	NOUN
eurjchem-1645	340	6	,	,	PUNCT
eurjchem-1645	340	7	cdcl3	cdcl3	PROPN
eurjchem-1645	340	8	,	,	PUNCT
eurjchem-1645	340	9	δ	δ	PROPN
eurjchem-1645	340	10	,	,	PUNCT
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eurjchem-1645	340	12	):	):	PUNCT
eurjchem-1645	340	13	12.72	12.72	NUM
eurjchem-1645	340	14	,	,	PUNCT
eurjchem-1645	340	15	49.24	49.24	NUM
eurjchem-1645	340	16	,	,	PUNCT
eurjchem-1645	340	17	52.46	52.46	NUM
eurjchem-1645	340	18	,	,	PUNCT
eurjchem-1645	340	19	55.46	55.46	NUM
eurjchem-1645	340	20	,	,	PUNCT
eurjchem-1645	340	21	97.8	97.8	NUM
eurjchem-1645	340	22	,	,	PUNCT
eurjchem-1645	340	23	103.21	103.21	NUM
eurjchem-1645	340	24	,	,	PUNCT
eurjchem-1645	340	25	106.67	106.67	NUM
eurjchem-1645	340	26	,	,	PUNCT
eurjchem-1645	340	27	127.34	127.34	NUM
eurjchem-1645	340	28	,	,	PUNCT
eurjchem-1645	340	29	127.84	127.84	NUM
eurjchem-1645	340	30	,	,	PUNCT
eurjchem-1645	340	31	128.22	128.22	NUM
eurjchem-1645	340	32	,	,	PUNCT
eurjchem-1645	340	33	128.42	128.42	NUM
eurjchem-1645	340	34	,	,	PUNCT
eurjchem-1645	340	35	128.88	128.88	NUM
eurjchem-1645	340	36	,	,	PUNCT
eurjchem-1645	340	37	129.42	129.42	NUM
eurjchem-1645	340	38	,	,	PUNCT
eurjchem-1645	340	39	129.41	129.41	NUM
eurjchem-1645	340	40	,	,	PUNCT
eurjchem-1645	340	41	130.71	130.71	NUM
eurjchem-1645	340	42	,	,	PUNCT
eurjchem-1645	340	43	130.85	130.85	NUM
eurjchem-1645	340	44	,	,	PUNCT
eurjchem-1645	340	45	145.21	145.21	NUM
eurjchem-1645	340	46	,	,	PUNCT
eurjchem-1645	340	47	148.73	148.73	NUM
eurjchem-1645	340	48	,	,	PUNCT
eurjchem-1645	340	49	150.65	150.65	NUM
eurjchem-1645	340	50	,	,	PUNCT
eurjchem-1645	340	51	162.10	162.10	NUM
eurjchem-1645	340	52	.	.	PUNCT
eurjchem-1645	341	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	341	2	(	(	PUNCT
eurjchem-1645	341	3	ei	ei	PROPN
eurjchem-1645	341	4	,	,	PUNCT
eurjchem-1645	341	5	m	m	PROPN
eurjchem-1645	341	6	/	/	SYM
eurjchem-1645	341	7	z	z	NOUN
eurjchem-1645	341	8	):	):	PUNCT
eurjchem-1645	341	9	357	357	NUM
eurjchem-1645	341	10	(	(	PUNCT
eurjchem-1645	341	11	m+h	m+h	NOUN
eurjchem-1645	341	12	)	)	PUNCT
eurjchem-1645	341	13	.	.	PUNCT
eurjchem-1645	342	1	anal	anal	PROPN
eurjchem-1645	342	2	.	.	PUNCT
eurjchem-1645	342	3	calcd	calcd	NOUN
eurjchem-1645	342	4	.	.	PUNCT
eurjchem-1645	343	1	for	for	ADP
eurjchem-1645	343	2	c22h20n4o	c22h20n4o	NOUN
eurjchem-1645	343	3	:	:	PUNCT
eurjchem-1645	343	4	c	c	X
eurjchem-1645	343	5	,	,	PUNCT
eurjchem-1645	343	6	74.14	74.14	NUM
eurjchem-1645	343	7	;	;	PUNCT
eurjchem-1645	343	8	h	h	NOUN
eurjchem-1645	343	9	,	,	PUNCT
eurjchem-1645	343	10	5.66	5.66	NUM
eurjchem-1645	343	11	;	;	PUNCT
eurjchem-1645	343	12	n	n	CCONJ
eurjchem-1645	343	13	,	,	PUNCT
eurjchem-1645	343	14	15.72	15.72	NUM
eurjchem-1645	343	15	.	.	PUNCT
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eurjchem-1645	343	17	:	:	PUNCT
eurjchem-1645	344	1	c	c	X
eurjchem-1645	344	2	,	,	PUNCT
eurjchem-1645	344	3	74.17	74.17	NUM
eurjchem-1645	344	4	;	;	PUNCT
eurjchem-1645	344	5	h	h	NOUN
eurjchem-1645	344	6	,	,	PUNCT
eurjchem-1645	344	7	5.65	5.65	NUM
eurjchem-1645	344	8	;	;	PUNCT
eurjchem-1645	344	9	n	n	CCONJ
eurjchem-1645	344	10	,	,	PUNCT
eurjchem-1645	344	11	15.71	15.71	NUM
eurjchem-1645	344	12	%	%	NOUN
eurjchem-1645	344	13	.	.	PUNCT
eurjchem-1645	345	1	hplc	hplc	NOUN
eurjchem-1645	345	2	:	:	PUNCT
eurjchem-1645	345	3	r.t	r.t	PROPN
eurjchem-1645	345	4	.	.	PUNCT
eurjchem-1645	346	1	=	=	NOUN
eurjchem-1645	346	2	4.89	4.89	NUM
eurjchem-1645	346	3	min	min	NOUN
eurjchem-1645	346	4	,	,	PUNCT
eurjchem-1645	346	5	purity	purity	NOUN
eurjchem-1645	346	6	=	=	NOUN
eurjchem-1645	346	7	96.6	96.6	NUM
eurjchem-1645	346	8	%	%	NOUN
eurjchem-1645	346	9	.	.	PUNCT
eurjchem-1645	347	1	5‐(4,5,6,7‐tetrahydro‐6‐(3‐methoxyphenyl)‐1h‐pyrazolo	5‐(4,5,6,7‐tetrahydro‐6‐(3‐methoxyphenyl)‐1h‐pyrazolo	NUM
eurjchem-1645	348	1	[	[	X
eurjchem-1645	348	2	3	3	NUM
eurjchem-1645	348	3	,	,	PUNCT
eurjchem-1645	348	4	4‐c]pyridin‐3‐yl)quinolone	4‐c]pyridin‐3‐yl)quinolone	NUM
eurjchem-1645	348	5	(	(	PUNCT
eurjchem-1645	348	6	13d	13d	NUM
eurjchem-1645	348	7	):	):	PUNCT
eurjchem-1645	348	8	color	color	NOUN
eurjchem-1645	348	9	:	:	PUNCT
eurjchem-1645	348	10	off	off	ADP
eurjchem-1645	348	11	white	white	PROPN
eurjchem-1645	348	12	.	.	PUNCT
eurjchem-1645	349	1	yield	yield	NOUN
eurjchem-1645	349	2	:	:	PUNCT
eurjchem-1645	349	3	86	86	NUM
eurjchem-1645	349	4	%	%	NOUN
eurjchem-1645	349	5	.	.	PUNCT
eurjchem-1645	350	1	m.p	m.p	PROPN
eurjchem-1645	350	2	.	.	PROPN
eurjchem-1645	350	3	:	:	PUNCT
eurjchem-1645	351	1	184‐185	184‐185	NUM
eurjchem-1645	351	2	°	°	PROPN
eurjchem-1645	351	3	c	c	PROPN
eurjchem-1645	351	4	.	.	PUNCT
eurjchem-1645	351	5	1h	1h	NUM
eurjchem-1645	351	6	nmr	nmr	NOUN
eurjchem-1645	351	7	(	(	PUNCT
eurjchem-1645	351	8	400	400	NUM
eurjchem-1645	351	9	mhz	mhz	NOUN
eurjchem-1645	351	10	,	,	PUNCT
eurjchem-1645	351	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	351	12	,	,	PUNCT
eurjchem-1645	351	13	δ	δ	PROPN
eurjchem-1645	351	14	,	,	PUNCT
eurjchem-1645	351	15	ppm	ppm	NUM
eurjchem-1645	351	16	):	):	PUNCT
eurjchem-1645	351	17	3.01	3.01	NUM
eurjchem-1645	351	18	(	(	PUNCT
eurjchem-1645	351	19	s	s	PROPN
eurjchem-1645	351	20	,	,	PUNCT
eurjchem-1645	351	21	2h	2h	NUM
eurjchem-1645	351	22	,	,	PUNCT
eurjchem-1645	351	23	ch2	ch2	PROPN
eurjchem-1645	351	24	)	)	PUNCT
eurjchem-1645	351	25	,	,	PUNCT
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eurjchem-1645	351	27	(	(	PUNCT
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eurjchem-1645	351	29	,	,	PUNCT
eurjchem-1645	351	30	2h	2h	NUM
eurjchem-1645	351	31	,	,	PUNCT
eurjchem-1645	351	32	ch2	ch2	PROPN
eurjchem-1645	351	33	)	)	PUNCT
eurjchem-1645	351	34	,	,	PUNCT
eurjchem-1645	351	35	3.76	3.76	NUM
eurjchem-1645	351	36	(	(	PUNCT
eurjchem-1645	351	37	s	s	PROPN
eurjchem-1645	351	38	,	,	PUNCT
eurjchem-1645	351	39	3h	3h	NUM
eurjchem-1645	351	40	,	,	PUNCT
eurjchem-1645	351	41	o‐ch3	o‐ch3	PROPN
eurjchem-1645	351	42	)	)	PUNCT
eurjchem-1645	351	43	,	,	PUNCT
eurjchem-1645	351	44	4.39	4.39	NUM
eurjchem-1645	351	45	(	(	PUNCT
eurjchem-1645	351	46	d	d	NOUN
eurjchem-1645	351	47	,	,	PUNCT
eurjchem-1645	351	48	2h	2h	NUM
eurjchem-1645	351	49	,	,	PUNCT
eurjchem-1645	351	50	j	j	PROPN
eurjchem-1645	351	51	pawar	pawar	PROPN
eurjchem-1645	351	52	et	et	PROPN
eurjchem-1645	351	53	al	al	PROPN
eurjchem-1645	351	54	.	.	PUNCT
eurjchem-1645	351	55	/	/	SYM
eurjchem-1645	351	56	european	european	PROPN
eurjchem-1645	351	57	journal	journal	PROPN
eurjchem-1645	351	58	of	of	ADP
eurjchem-1645	351	59	chemistry	chemistry	NOUN
eurjchem-1645	351	60	8	8	NUM
eurjchem-1645	351	61	(	(	PUNCT
eurjchem-1645	351	62	4	4	NUM
eurjchem-1645	351	63	)	)	PUNCT
eurjchem-1645	351	64	(	(	PUNCT
eurjchem-1645	351	65	2017	2017	NUM
eurjchem-1645	351	66	)	)	PUNCT
eurjchem-1645	351	67	400‐409	400‐409	NUM
eurjchem-1645	351	68	405	405	NUM
eurjchem-1645	351	69	=	=	SYM
eurjchem-1645	351	70	8	8	NUM
eurjchem-1645	351	71	hz	hz	NOUN
eurjchem-1645	351	72	,	,	PUNCT
eurjchem-1645	351	73	n‐ch2	n‐ch2	PROPN
eurjchem-1645	351	74	)	)	PUNCT
eurjchem-1645	351	75	,	,	PUNCT
eurjchem-1645	351	76	6.38	6.38	NUM
eurjchem-1645	351	77	(	(	PUNCT
eurjchem-1645	351	78	t	t	PROPN
eurjchem-1645	351	79	,	,	PUNCT
eurjchem-1645	351	80	1h	1h	NUM
eurjchem-1645	351	81	,	,	PUNCT
eurjchem-1645	351	82	j	j	PROPN
eurjchem-1645	351	83	=	=	SYM
eurjchem-1645	351	84	7.6	7.6	NUM
eurjchem-1645	351	85	hz	hz	NOUN
eurjchem-1645	351	86	,	,	PUNCT
eurjchem-1645	351	87	ar‐h	ar‐h	PROPN
eurjchem-1645	351	88	)	)	PUNCT
eurjchem-1645	351	89	,	,	PUNCT
eurjchem-1645	351	90	6.58	6.58	NUM
eurjchem-1645	351	91	(	(	PUNCT
eurjchem-1645	351	92	s	s	PROPN
eurjchem-1645	351	93	,	,	PUNCT
eurjchem-1645	351	94	1h	1h	NUM
eurjchem-1645	351	95	,	,	PUNCT
eurjchem-1645	351	96	ar‐h	ar‐h	NOUN
eurjchem-1645	351	97	)	)	PUNCT
eurjchem-1645	351	98	,	,	PUNCT
eurjchem-1645	351	99	6.65	6.65	NUM
eurjchem-1645	351	100	(	(	PUNCT
eurjchem-1645	351	101	t	t	PROPN
eurjchem-1645	351	102	,	,	PUNCT
eurjchem-1645	351	103	1h	1h	NUM
eurjchem-1645	351	104	,	,	PUNCT
eurjchem-1645	351	105	j	j	PROPN
eurjchem-1645	351	106	=	=	SYM
eurjchem-1645	351	107	7.6	7.6	NUM
eurjchem-1645	351	108	hz	hz	NOUN
eurjchem-1645	351	109	,	,	PUNCT
eurjchem-1645	351	110	ar‐h	ar‐h	PROPN
eurjchem-1645	351	111	)	)	PUNCT
eurjchem-1645	351	112	,	,	PUNCT
eurjchem-1645	351	113	7.16	7.16	NUM
eurjchem-1645	351	114	(	(	PUNCT
eurjchem-1645	351	115	d	d	PROPN
eurjchem-1645	351	116	,	,	PUNCT
eurjchem-1645	351	117	1h	1h	NUM
eurjchem-1645	351	118	,	,	PUNCT
eurjchem-1645	351	119	j	j	PROPN
eurjchem-1645	351	120	=	=	PROPN
eurjchem-1645	351	121	8.8	8.8	NUM
eurjchem-1645	351	122	hz	hz	NOUN
eurjchem-1645	351	123	,	,	PUNCT
eurjchem-1645	351	124	ar‐h	ar‐h	PROPN
eurjchem-1645	351	125	)	)	PUNCT
eurjchem-1645	351	126	,	,	PUNCT
eurjchem-1645	351	127	7.8‐	7.8‐	NUM
eurjchem-1645	351	128	7.58	7.58	NUM
eurjchem-1645	351	129	(	(	PUNCT
eurjchem-1645	351	130	m	m	PROPN
eurjchem-1645	351	131	,	,	PUNCT
eurjchem-1645	351	132	2h	2h	NUM
eurjchem-1645	351	133	,	,	PUNCT
eurjchem-1645	351	134	ar‐h	ar‐h	NOUN
eurjchem-1645	351	135	)	)	PUNCT
eurjchem-1645	351	136	,	,	PUNCT
eurjchem-1645	351	137	8.18‐8.01	8.18‐8.01	NUM
eurjchem-1645	351	138	(	(	PUNCT
eurjchem-1645	351	139	m	m	PROPN
eurjchem-1645	351	140	,	,	PUNCT
eurjchem-1645	351	141	2h	2h	NUM
eurjchem-1645	351	142	,	,	PUNCT
eurjchem-1645	351	143	ar‐h	ar‐h	NOUN
eurjchem-1645	351	144	)	)	PUNCT
eurjchem-1645	351	145	,	,	PUNCT
eurjchem-1645	351	146	8.43	8.43	NUM
eurjchem-1645	351	147	(	(	PUNCT
eurjchem-1645	351	148	s	s	PROPN
eurjchem-1645	351	149	,	,	PUNCT
eurjchem-1645	351	150	1h	1h	NUM
eurjchem-1645	351	151	,	,	PUNCT
eurjchem-1645	351	152	ar‐h	ar‐h	NOUN
eurjchem-1645	351	153	)	)	PUNCT
eurjchem-1645	351	154	,	,	PUNCT
eurjchem-1645	351	155	9.38	9.38	NUM
eurjchem-1645	351	156	&	&	CCONJ
eurjchem-1645	351	157	9.20	9.20	NUM
eurjchem-1645	351	158	(	(	PUNCT
eurjchem-1645	351	159	s	s	PROPN
eurjchem-1645	351	160	,	,	PUNCT
eurjchem-1645	351	161	1h	1h	NUM
eurjchem-1645	351	162	,	,	PUNCT
eurjchem-1645	351	163	ar‐h	ar‐h	NOUN
eurjchem-1645	351	164	)	)	PUNCT
eurjchem-1645	351	165	,	,	PUNCT
eurjchem-1645	351	166	13.2	13.2	NUM
eurjchem-1645	351	167	(	(	PUNCT
eurjchem-1645	351	168	br	br	PROPN
eurjchem-1645	351	169	,	,	PUNCT
eurjchem-1645	351	170	1h	1h	NUM
eurjchem-1645	351	171	,	,	PUNCT
eurjchem-1645	351	172	nh	nh	PROPN
eurjchem-1645	351	173	,	,	PUNCT
eurjchem-1645	351	174	1h	1h	NUM
eurjchem-1645	351	175	)	)	PUNCT
eurjchem-1645	351	176	.	.	PUNCT
eurjchem-1645	352	1	13c	13c	NOUN
eurjchem-1645	352	2	nmr	nmr	NOUN
eurjchem-1645	352	3	(	(	PUNCT
eurjchem-1645	352	4	100	100	NUM
eurjchem-1645	352	5	mhz	mhz	NOUN
eurjchem-1645	352	6	,	,	PUNCT
eurjchem-1645	352	7	cdcl3	cdcl3	PROPN
eurjchem-1645	352	8	,	,	PUNCT
eurjchem-1645	352	9	δ	δ	PROPN
eurjchem-1645	352	10	,	,	PUNCT
eurjchem-1645	352	11	ppm	ppm	NOUN
eurjchem-1645	352	12	):	):	PUNCT
eurjchem-1645	352	13	12.62	12.62	NUM
eurjchem-1645	352	14	,	,	PUNCT
eurjchem-1645	352	15	49.34	49.34	NUM
eurjchem-1645	352	16	,	,	PUNCT
eurjchem-1645	352	17	52.56	52.56	NUM
eurjchem-1645	352	18	,	,	PUNCT
eurjchem-1645	352	19	54.46	54.46	NUM
eurjchem-1645	352	20	,	,	PUNCT
eurjchem-1645	352	21	97.86	97.86	NUM
eurjchem-1645	352	22	,	,	PUNCT
eurjchem-1645	352	23	102.21	102.21	NUM
eurjchem-1645	352	24	,	,	PUNCT
eurjchem-1645	352	25	106.77	106.77	NUM
eurjchem-1645	352	26	,	,	PUNCT
eurjchem-1645	352	27	127.44	127.44	NUM
eurjchem-1645	352	28	,	,	PUNCT
eurjchem-1645	352	29	127.84	127.84	NUM
eurjchem-1645	352	30	,	,	PUNCT
eurjchem-1645	352	31	128.32	128.32	NUM
eurjchem-1645	352	32	,	,	PUNCT
eurjchem-1645	352	33	128.42	128.42	NUM
eurjchem-1645	352	34	,	,	PUNCT
eurjchem-1645	352	35	128.88	128.88	NUM
eurjchem-1645	352	36	,	,	PUNCT
eurjchem-1645	352	37	129.42	129.42	NUM
eurjchem-1645	352	38	,	,	PUNCT
eurjchem-1645	352	39	129.40	129.40	NUM
eurjchem-1645	352	40	,	,	PUNCT
eurjchem-1645	352	41	130.60	130.60	NUM
eurjchem-1645	352	42	,	,	PUNCT
eurjchem-1645	352	43	130.85	130.85	NUM
eurjchem-1645	352	44	,	,	PUNCT
eurjchem-1645	352	45	145.31	145.31	NUM
eurjchem-1645	352	46	,	,	PUNCT
eurjchem-1645	352	47	148.63	148.63	NUM
eurjchem-1645	352	48	,	,	PUNCT
eurjchem-1645	352	49	151.14	151.14	NUM
eurjchem-1645	352	50	,	,	PUNCT
eurjchem-1645	352	51	162.60	162.60	NUM
eurjchem-1645	352	52	.	.	PUNCT
eurjchem-1645	353	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	353	2	(	(	PUNCT
eurjchem-1645	353	3	ei	ei	PROPN
eurjchem-1645	353	4	,	,	PUNCT
eurjchem-1645	353	5	m	m	PROPN
eurjchem-1645	353	6	/	/	SYM
eurjchem-1645	353	7	z	z	NOUN
eurjchem-1645	353	8	):	):	PUNCT
eurjchem-1645	353	9	357	357	NUM
eurjchem-1645	353	10	(	(	PUNCT
eurjchem-1645	353	11	m+h	m+h	NOUN
eurjchem-1645	353	12	)	)	PUNCT
eurjchem-1645	353	13	.	.	PUNCT
eurjchem-1645	354	1	anal	anal	PROPN
eurjchem-1645	354	2	.	.	PUNCT
eurjchem-1645	354	3	calcd	calcd	NOUN
eurjchem-1645	354	4	.	.	PUNCT
eurjchem-1645	355	1	for	for	ADP
eurjchem-1645	355	2	c22h20n4o	c22h20n4o	NOUN
eurjchem-1645	355	3	:	:	PUNCT
eurjchem-1645	355	4	c	c	X
eurjchem-1645	355	5	,	,	PUNCT
eurjchem-1645	355	6	74.14	74.14	NUM
eurjchem-1645	355	7	;	;	PUNCT
eurjchem-1645	355	8	h	h	NOUN
eurjchem-1645	355	9	,	,	PUNCT
eurjchem-1645	355	10	5.66	5.66	NUM
eurjchem-1645	355	11	;	;	PUNCT
eurjchem-1645	355	12	n	n	CCONJ
eurjchem-1645	355	13	,	,	PUNCT
eurjchem-1645	355	14	15.72	15.72	NUM
eurjchem-1645	355	15	.	.	PUNCT
eurjchem-1645	355	16	found	find	VERB
eurjchem-1645	355	17	:	:	PUNCT
eurjchem-1645	356	1	c	c	X
eurjchem-1645	356	2	,	,	PUNCT
eurjchem-1645	356	3	74.11	74.11	NUM
eurjchem-1645	356	4	;	;	PUNCT
eurjchem-1645	356	5	h	h	NOUN
eurjchem-1645	356	6	,	,	PUNCT
eurjchem-1645	356	7	5.69	5.69	NUM
eurjchem-1645	356	8	;	;	PUNCT
eurjchem-1645	356	9	n	n	CCONJ
eurjchem-1645	356	10	,	,	PUNCT
eurjchem-1645	356	11	15.71	15.71	NUM
eurjchem-1645	356	12	%	%	NOUN
eurjchem-1645	356	13	.	.	PUNCT
eurjchem-1645	357	1	hplc	hplc	NOUN
eurjchem-1645	357	2	:	:	PUNCT
eurjchem-1645	357	3	r.t	r.t	PROPN
eurjchem-1645	357	4	.	.	PUNCT
eurjchem-1645	357	5	=	=	NOUN
eurjchem-1645	357	6	5.09	5.09	NUM
eurjchem-1645	357	7	min	min	NOUN
eurjchem-1645	357	8	,	,	PUNCT
eurjchem-1645	357	9	purity	purity	NOUN
eurjchem-1645	357	10	=	=	NOUN
eurjchem-1645	357	11	98.0	98.0	NUM
eurjchem-1645	357	12	%	%	NOUN
eurjchem-1645	357	13	.	.	PUNCT
eurjchem-1645	358	1	3‐(benzofuran‐2‐yl)‐4	3‐(benzofuran‐2‐yl)‐4	NUM
eurjchem-1645	358	2	,	,	PUNCT
eurjchem-1645	358	3	5	5	NUM
eurjchem-1645	358	4	,	,	PUNCT
eurjchem-1645	358	5	6	6	NUM
eurjchem-1645	358	6	,	,	PUNCT
eurjchem-1645	358	7	7‐tetrahydro‐6‐(pyrimidin‐2‐yl)‐	7‐tetrahydro‐6‐(pyrimidin‐2‐yl)‐	NUM
eurjchem-1645	358	8	1h‐pyrazolo[3,4‐c]pyridine	1h‐pyrazolo[3,4‐c]pyridine	NUM
eurjchem-1645	358	9	(	(	PUNCT
eurjchem-1645	358	10	13e	13e	NUM
eurjchem-1645	358	11	):	):	PUNCT
eurjchem-1645	358	12	color	color	NOUN
eurjchem-1645	358	13	:	:	PUNCT
eurjchem-1645	358	14	yellow	yellow	ADJ
eurjchem-1645	358	15	.	.	PUNCT
eurjchem-1645	359	1	yield	yield	NOUN
eurjchem-1645	359	2	:	:	PUNCT
eurjchem-1645	359	3	88	88	NUM
eurjchem-1645	359	4	%	%	NOUN
eurjchem-1645	359	5	.	.	PUNCT
eurjchem-1645	360	1	m.p	m.p	PROPN
eurjchem-1645	360	2	.	.	PROPN
eurjchem-1645	360	3	:	:	PUNCT
eurjchem-1645	361	1	167‐168	167‐168	NUM
eurjchem-1645	361	2	°	°	PROPN
eurjchem-1645	361	3	c	c	PROPN
eurjchem-1645	361	4	.	.	PUNCT
eurjchem-1645	362	1	1h	1h	NUM
eurjchem-1645	362	2	nmr	nmr	NOUN
eurjchem-1645	362	3	(	(	PUNCT
eurjchem-1645	362	4	400	400	NUM
eurjchem-1645	362	5	mhz	mhz	NOUN
eurjchem-1645	362	6	,	,	PUNCT
eurjchem-1645	362	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	362	8	,	,	PUNCT
eurjchem-1645	362	9	δ	δ	PROPN
eurjchem-1645	362	10	,	,	PUNCT
eurjchem-1645	362	11	ppm	ppm	NUM
eurjchem-1645	362	12	):	):	PUNCT
eurjchem-1645	362	13	2.86	2.86	NUM
eurjchem-1645	362	14	(	(	PUNCT
eurjchem-1645	362	15	d	d	PROPN
eurjchem-1645	362	16	,	,	PUNCT
eurjchem-1645	362	17	2h	2h	NUM
eurjchem-1645	362	18	,	,	PUNCT
eurjchem-1645	362	19	j	j	PROPN
eurjchem-1645	362	20	=	=	SYM
eurjchem-1645	362	21	8hz	8hz	NOUN
eurjchem-1645	362	22	,	,	PUNCT
eurjchem-1645	362	23	ch2	ch2	PROPN
eurjchem-1645	362	24	)	)	PUNCT
eurjchem-1645	362	25	,	,	PUNCT
eurjchem-1645	362	26	4.08	4.08	NUM
eurjchem-1645	362	27	(	(	PUNCT
eurjchem-1645	362	28	s	s	PROPN
eurjchem-1645	362	29	,	,	PUNCT
eurjchem-1645	362	30	2h	2h	NUM
eurjchem-1645	362	31	,	,	PUNCT
eurjchem-1645	362	32	ch2	ch2	PROPN
eurjchem-1645	362	33	)	)	PUNCT
eurjchem-1645	362	34	,	,	PUNCT
eurjchem-1645	362	35	4.96	4.96	NUM
eurjchem-1645	362	36	(	(	PUNCT
eurjchem-1645	362	37	d	d	NOUN
eurjchem-1645	362	38	,	,	PUNCT
eurjchem-1645	362	39	2h	2h	NUM
eurjchem-1645	362	40	,	,	PUNCT
eurjchem-1645	362	41	j	j	PROPN
eurjchem-1645	362	42	=	=	SYM
eurjchem-1645	362	43	7.8	7.8	NUM
eurjchem-1645	362	44	hz	hz	VERB
eurjchem-1645	362	45	,	,	PUNCT
eurjchem-1645	362	46	n‐	n‐	NOUN
eurjchem-1645	362	47	ch2	ch2	PROPN
eurjchem-1645	362	48	)	)	PUNCT
eurjchem-1645	362	49	,	,	PUNCT
eurjchem-1645	362	50	6.65	6.65	NUM
eurjchem-1645	362	51	(	(	PUNCT
eurjchem-1645	362	52	s	s	PROPN
eurjchem-1645	362	53	,	,	PUNCT
eurjchem-1645	362	54	1h	1h	NUM
eurjchem-1645	362	55	,	,	PUNCT
eurjchem-1645	362	56	ar‐h	ar‐h	NOUN
eurjchem-1645	362	57	)	)	PUNCT
eurjchem-1645	362	58	,	,	PUNCT
eurjchem-1645	362	59	7.16‐7.02	7.16‐7.02	NUM
eurjchem-1645	362	60	(	(	PUNCT
eurjchem-1645	362	61	d	d	PROPN
eurjchem-1645	362	62	,	,	PUNCT
eurjchem-1645	362	63	1h	1h	NUM
eurjchem-1645	362	64	,	,	PUNCT
eurjchem-1645	362	65	ar‐h	ar‐h	NOUN
eurjchem-1645	362	66	)	)	PUNCT
eurjchem-1645	362	67	,	,	PUNCT
eurjchem-1645	362	68	7.49‐7.21	7.49‐7.21	NUM
eurjchem-1645	362	69	(	(	PUNCT
eurjchem-1645	362	70	m	m	PROPN
eurjchem-1645	362	71	,	,	PUNCT
eurjchem-1645	362	72	2h	2h	NUM
eurjchem-1645	362	73	,	,	PUNCT
eurjchem-1645	362	74	ar‐h	ar‐h	NOUN
eurjchem-1645	362	75	)	)	PUNCT
eurjchem-1645	362	76	,	,	PUNCT
eurjchem-1645	362	77	7.76‐7.6	7.76‐7.6	NUM
eurjchem-1645	362	78	(	(	PUNCT
eurjchem-1645	362	79	m	m	PROPN
eurjchem-1645	362	80	,	,	PUNCT
eurjchem-1645	362	81	2h	2h	NUM
eurjchem-1645	362	82	,	,	PUNCT
eurjchem-1645	362	83	ar‐h	ar‐h	NOUN
eurjchem-1645	362	84	)	)	PUNCT
eurjchem-1645	362	85	,	,	PUNCT
eurjchem-1645	362	86	8.42	8.42	NUM
eurjchem-1645	362	87	(	(	PUNCT
eurjchem-1645	362	88	s	s	PROPN
eurjchem-1645	362	89	,	,	PUNCT
eurjchem-1645	362	90	2h	2h	NUM
eurjchem-1645	362	91	,	,	PUNCT
eurjchem-1645	362	92	ar‐h	ar‐h	NOUN
eurjchem-1645	362	93	)	)	PUNCT
eurjchem-1645	362	94	,	,	PUNCT
eurjchem-1645	362	95	13.4	13.4	NUM
eurjchem-1645	362	96	&	&	CCONJ
eurjchem-1645	362	97	12.9	12.9	NUM
eurjchem-1645	362	98	(	(	PUNCT
eurjchem-1645	362	99	br	br	PROPN
eurjchem-1645	362	100	.	.	PROPN
eurjchem-1645	363	1	s	s	PART
eurjchem-1645	363	2	,	,	PUNCT
eurjchem-1645	363	3	1h	1h	NUM
eurjchem-1645	363	4	,	,	PUNCT
eurjchem-1645	363	5	nh	nh	PROPN
eurjchem-1645	363	6	)	)	PUNCT
eurjchem-1645	363	7	.	.	PUNCT
eurjchem-1645	364	1	13c	13c	NOUN
eurjchem-1645	364	2	nmr	nmr	NOUN
eurjchem-1645	364	3	(	(	PUNCT
eurjchem-1645	364	4	100	100	NUM
eurjchem-1645	364	5	mhz	mhz	NOUN
eurjchem-1645	364	6	,	,	PUNCT
eurjchem-1645	364	7	cdcl3	cdcl3	PROPN
eurjchem-1645	364	8	,	,	PUNCT
eurjchem-1645	364	9	δ	δ	PROPN
eurjchem-1645	364	10	,	,	PUNCT
eurjchem-1645	364	11	ppm	ppm	NOUN
eurjchem-1645	364	12	):	):	PUNCT
eurjchem-1645	364	13	10.41	10.41	NUM
eurjchem-1645	364	14	,	,	PUNCT
eurjchem-1645	364	15	48.67	48.67	NUM
eurjchem-1645	364	16	,	,	PUNCT
eurjchem-1645	364	17	51.72	51.72	NUM
eurjchem-1645	364	18	,	,	PUNCT
eurjchem-1645	364	19	102.82	102.82	NUM
eurjchem-1645	364	20	,	,	PUNCT
eurjchem-1645	364	21	103.03	103.03	NUM
eurjchem-1645	364	22	,	,	PUNCT
eurjchem-1645	364	23	110.62	110.62	NUM
eurjchem-1645	364	24	,	,	PUNCT
eurjchem-1645	364	25	111.67	111.67	NUM
eurjchem-1645	364	26	,	,	PUNCT
eurjchem-1645	364	27	121.12	121.12	NUM
eurjchem-1645	364	28	,	,	PUNCT
eurjchem-1645	364	29	123.46	123.46	NUM
eurjchem-1645	364	30	,	,	PUNCT
eurjchem-1645	364	31	123.86	123.86	NUM
eurjchem-1645	364	32	,	,	PUNCT
eurjchem-1645	364	33	135.40	135.40	NUM
eurjchem-1645	364	34	,	,	PUNCT
eurjchem-1645	364	35	144.20	144.20	NUM
eurjchem-1645	364	36	,	,	PUNCT
eurjchem-1645	364	37	150.66	150.66	NUM
eurjchem-1645	364	38	,	,	PUNCT
eurjchem-1645	364	39	162.84	162.84	NUM
eurjchem-1645	364	40	,	,	PUNCT
eurjchem-1645	364	41	175.88	175.88	NUM
eurjchem-1645	364	42	.	.	PUNCT
eurjchem-1645	365	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	365	2	(	(	PUNCT
eurjchem-1645	365	3	ei	ei	PROPN
eurjchem-1645	365	4	,	,	PUNCT
eurjchem-1645	365	5	m	m	PROPN
eurjchem-1645	365	6	/	/	SYM
eurjchem-1645	365	7	z	z	NOUN
eurjchem-1645	365	8	):	):	PUNCT
eurjchem-1645	365	9	318	318	NUM
eurjchem-1645	365	10	(	(	PUNCT
eurjchem-1645	365	11	m+h	m+h	PROPN
eurjchem-1645	365	12	)	)	PUNCT
eurjchem-1645	365	13	.	.	PUNCT
eurjchem-1645	366	1	anal	anal	PROPN
eurjchem-1645	366	2	.	.	PUNCT
eurjchem-1645	366	3	calcd	calcd	NOUN
eurjchem-1645	366	4	.	.	PUNCT
eurjchem-1645	367	1	for	for	ADP
eurjchem-1645	367	2	c18h15n5o	c18h15n5o	NOUN
eurjchem-1645	367	3	:	:	PUNCT
eurjchem-1645	368	1	c	c	X
eurjchem-1645	368	2	,	,	PUNCT
eurjchem-1645	368	3	68.13	68.13	NUM
eurjchem-1645	368	4	;	;	PUNCT
eurjchem-1645	369	1	h	h	NOUN
eurjchem-1645	369	2	,	,	PUNCT
eurjchem-1645	369	3	4.46	4.46	NUM
eurjchem-1645	369	4	;	;	PUNCT
eurjchem-1645	369	5	n	n	CCONJ
eurjchem-1645	369	6	,	,	PUNCT
eurjchem-1645	369	7	22.07	22.07	NUM
eurjchem-1645	369	8	.	.	PUNCT
eurjchem-1645	369	9	found	find	VERB
eurjchem-1645	369	10	:	:	PUNCT
eurjchem-1645	370	1	c	c	X
eurjchem-1645	370	2	,	,	PUNCT
eurjchem-1645	370	3	68.11	68.11	NUM
eurjchem-1645	370	4	;	;	PUNCT
eurjchem-1645	370	5	h	h	X
eurjchem-1645	370	6	,	,	PUNCT
eurjchem-1645	370	7	4.48	4.48	NUM
eurjchem-1645	370	8	;	;	PUNCT
eurjchem-1645	370	9	n	n	CCONJ
eurjchem-1645	370	10	,	,	PUNCT
eurjchem-1645	370	11	22.09	22.09	NUM
eurjchem-1645	370	12	%	%	NOUN
eurjchem-1645	370	13	.	.	PUNCT
eurjchem-1645	371	1	hplc	hplc	NOUN
eurjchem-1645	371	2	:	:	PUNCT
eurjchem-1645	371	3	r.t	r.t	PROPN
eurjchem-1645	371	4	.	.	PUNCT
eurjchem-1645	371	5	=	=	PROPN
eurjchem-1645	371	6	7.58	7.58	NUM
eurjchem-1645	371	7	min	min	NOUN
eurjchem-1645	371	8	,	,	PUNCT
eurjchem-1645	371	9	purity	purity	NOUN
eurjchem-1645	371	10	=	=	PUNCT
eurjchem-1645	371	11	93.7	93.7	NUM
eurjchem-1645	371	12	%	%	NOUN
eurjchem-1645	371	13	.	.	PUNCT
eurjchem-1645	372	1	3‐(benzo[b]thiophen‐2‐yl)‐4	3‐(benzo[b]thiophen‐2‐yl)‐4	NUM
eurjchem-1645	372	2	,	,	PUNCT
eurjchem-1645	372	3	5	5	NUM
eurjchem-1645	372	4	,	,	PUNCT
eurjchem-1645	372	5	6,7‐tetrahydro‐6‐(pyrimidin‐	6,7‐tetrahydro‐6‐(pyrimidin‐	PROPN
eurjchem-1645	372	6	2‐yl)‐1h‐pyrazolo[3,4‐c]pyridine	2‐yl)‐1h‐pyrazolo[3,4‐c]pyridine	NUM
eurjchem-1645	372	7	(	(	PUNCT
eurjchem-1645	372	8	13f	13f	NUM
eurjchem-1645	372	9	):	):	PUNCT
eurjchem-1645	372	10	color	color	NOUN
eurjchem-1645	372	11	:	:	PUNCT
eurjchem-1645	372	12	yellow	yellow	ADJ
eurjchem-1645	372	13	.	.	PUNCT
eurjchem-1645	373	1	yield	yield	NOUN
eurjchem-1645	373	2	:	:	PUNCT
eurjchem-1645	373	3	91	91	NUM
eurjchem-1645	373	4	%	%	NOUN
eurjchem-1645	373	5	.	.	PUNCT
eurjchem-1645	374	1	m.p	m.p	PROPN
eurjchem-1645	374	2	.	.	PROPN
eurjchem-1645	374	3	:	:	PUNCT
eurjchem-1645	375	1	197‐198	197‐198	NUM
eurjchem-1645	375	2	°	°	PROPN
eurjchem-1645	375	3	c	c	PROPN
eurjchem-1645	375	4	.	.	PUNCT
eurjchem-1645	375	5	1h	1h	NUM
eurjchem-1645	375	6	nmr	nmr	NOUN
eurjchem-1645	375	7	(	(	PUNCT
eurjchem-1645	375	8	400	400	NUM
eurjchem-1645	375	9	mhz	mhz	NOUN
eurjchem-1645	375	10	,	,	PUNCT
eurjchem-1645	375	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	375	12	,	,	PUNCT
eurjchem-1645	375	13	δ	δ	PROPN
eurjchem-1645	375	14	,	,	PUNCT
eurjchem-1645	375	15	ppm	ppm	NOUN
eurjchem-1645	375	16	):	):	PUNCT
eurjchem-1645	375	17	3.06	3.06	NUM
eurjchem-1645	375	18	(	(	PUNCT
eurjchem-1645	375	19	d	d	PROPN
eurjchem-1645	375	20	,	,	PUNCT
eurjchem-1645	375	21	2h	2h	NUM
eurjchem-1645	375	22	,	,	PUNCT
eurjchem-1645	375	23	j	j	PROPN
eurjchem-1645	375	24	=	=	PROPN
eurjchem-1645	375	25	8.2	8.2	NUM
eurjchem-1645	375	26	hz	hz	NOUN
eurjchem-1645	375	27	,	,	PUNCT
eurjchem-1645	375	28	ch2	ch2	PROPN
eurjchem-1645	375	29	)	)	PUNCT
eurjchem-1645	375	30	,	,	PUNCT
eurjchem-1645	375	31	4.18	4.18	NUM
eurjchem-1645	375	32	(	(	PUNCT
eurjchem-1645	375	33	s	s	PROPN
eurjchem-1645	375	34	,	,	PUNCT
eurjchem-1645	375	35	2h	2h	NUM
eurjchem-1645	375	36	,	,	PUNCT
eurjchem-1645	375	37	ch2	ch2	PROPN
eurjchem-1645	375	38	)	)	PUNCT
eurjchem-1645	375	39	,	,	PUNCT
eurjchem-1645	375	40	4.96	4.96	NUM
eurjchem-1645	375	41	(	(	PUNCT
eurjchem-1645	375	42	d	d	NOUN
eurjchem-1645	375	43	,	,	PUNCT
eurjchem-1645	375	44	2h	2h	NUM
eurjchem-1645	375	45	,	,	PUNCT
eurjchem-1645	375	46	j	j	PROPN
eurjchem-1645	375	47	=	=	SYM
eurjchem-1645	375	48	7.6	7.6	NUM
eurjchem-1645	375	49	hz	hz	NOUN
eurjchem-1645	375	50	,	,	PUNCT
eurjchem-1645	375	51	n‐ch2	n‐ch2	PROPN
eurjchem-1645	375	52	)	)	PUNCT
eurjchem-1645	375	53	,	,	PUNCT
eurjchem-1645	375	54	6.66	6.66	NUM
eurjchem-1645	375	55	(	(	PUNCT
eurjchem-1645	375	56	s	s	PROPN
eurjchem-1645	375	57	,	,	PUNCT
eurjchem-1645	375	58	1h	1h	NUM
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eurjchem-1645	375	62	,	,	PUNCT
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eurjchem-1645	375	67	1h	1h	NUM
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eurjchem-1645	375	71	,	,	PUNCT
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eurjchem-1645	375	75	m	m	PROPN
eurjchem-1645	375	76	,	,	PUNCT
eurjchem-1645	375	77	2h	2h	NUM
eurjchem-1645	375	78	,	,	PUNCT
eurjchem-1645	375	79	ar‐h	ar‐h	NOUN
eurjchem-1645	375	80	)	)	PUNCT
eurjchem-1645	375	81	,	,	PUNCT
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eurjchem-1645	375	84	m	m	PROPN
eurjchem-1645	375	85	,	,	PUNCT
eurjchem-1645	375	86	2h	2h	NUM
eurjchem-1645	375	87	,	,	PUNCT
eurjchem-1645	375	88	ar‐h	ar‐h	NOUN
eurjchem-1645	375	89	)	)	PUNCT
eurjchem-1645	375	90	,	,	PUNCT
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eurjchem-1645	375	92	(	(	PUNCT
eurjchem-1645	375	93	s	s	PROPN
eurjchem-1645	375	94	,	,	PUNCT
eurjchem-1645	375	95	2h	2h	NUM
eurjchem-1645	375	96	,	,	PUNCT
eurjchem-1645	375	97	ar‐h	ar‐h	NOUN
eurjchem-1645	375	98	)	)	PUNCT
eurjchem-1645	375	99	,	,	PUNCT
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eurjchem-1645	375	101	&	&	CCONJ
eurjchem-1645	375	102	12.0	12.0	NUM
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eurjchem-1645	375	104	br	br	PROPN
eurjchem-1645	375	105	.	.	PROPN
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eurjchem-1645	377	40	,	,	PUNCT
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eurjchem-1645	378	9	334	334	NUM
eurjchem-1645	378	10	(	(	PUNCT
eurjchem-1645	378	11	m+h	m+h	NOUN
eurjchem-1645	378	12	)	)	PUNCT
eurjchem-1645	378	13	.	.	PUNCT
eurjchem-1645	379	1	anal	anal	PROPN
eurjchem-1645	379	2	.	.	PUNCT
eurjchem-1645	379	3	calcd	calcd	NOUN
eurjchem-1645	379	4	.	.	PUNCT
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eurjchem-1645	380	2	c18h15n5s	c18h15n5s	PROPN
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eurjchem-1645	380	4	c	c	X
eurjchem-1645	380	5	,	,	PUNCT
eurjchem-1645	380	6	64.84	64.84	NUM
eurjchem-1645	380	7	;	;	PUNCT
eurjchem-1645	380	8	h	h	NOUN
eurjchem-1645	380	9	,	,	PUNCT
eurjchem-1645	380	10	4.53	4.53	NUM
eurjchem-1645	380	11	;	;	PUNCT
eurjchem-1645	380	12	n	n	CCONJ
eurjchem-1645	380	13	,	,	PUNCT
eurjchem-1645	380	14	21.01	21.01	NUM
eurjchem-1645	380	15	.	.	PUNCT
eurjchem-1645	380	16	found	find	VERB
eurjchem-1645	380	17	:	:	PUNCT
eurjchem-1645	381	1	c	c	X
eurjchem-1645	381	2	,	,	PUNCT
eurjchem-1645	381	3	64.86	64.86	NUM
eurjchem-1645	381	4	;	;	PUNCT
eurjchem-1645	382	1	h	h	NOUN
eurjchem-1645	382	2	,	,	PUNCT
eurjchem-1645	382	3	4.51	4.51	NUM
eurjchem-1645	382	4	;	;	PUNCT
eurjchem-1645	382	5	n	n	CCONJ
eurjchem-1645	382	6	,	,	PUNCT
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eurjchem-1645	382	9	.	.	PUNCT
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eurjchem-1645	383	2	:	:	PUNCT
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eurjchem-1645	383	4	.	.	PUNCT
eurjchem-1645	384	1	=	=	NOUN
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eurjchem-1645	384	4	,	,	PUNCT
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eurjchem-1645	384	9	.	.	PUNCT
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eurjchem-1645	385	8	):	):	PUNCT
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eurjchem-1645	385	14	:	:	PUNCT
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eurjchem-1645	387	4	.	.	PUNCT
eurjchem-1645	388	1	1h	1h	NUM
eurjchem-1645	388	2	nmr	nmr	NOUN
eurjchem-1645	388	3	(	(	PUNCT
eurjchem-1645	388	4	400	400	NUM
eurjchem-1645	388	5	mhz	mhz	NOUN
eurjchem-1645	388	6	,	,	PUNCT
eurjchem-1645	388	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	388	8	,	,	PUNCT
eurjchem-1645	388	9	δ	δ	PROPN
eurjchem-1645	388	10	,	,	PUNCT
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eurjchem-1645	388	12	):	):	PUNCT
eurjchem-1645	388	13	2.92	2.92	NUM
eurjchem-1645	388	14	(	(	PUNCT
eurjchem-1645	388	15	d	d	PROPN
eurjchem-1645	388	16	,	,	PUNCT
eurjchem-1645	388	17	2h	2h	NUM
eurjchem-1645	388	18	,	,	PUNCT
eurjchem-1645	388	19	j	j	PROPN
eurjchem-1645	388	20	=	=	PROPN
eurjchem-1645	388	21	8.4	8.4	NUM
eurjchem-1645	388	22	hz	hz	NOUN
eurjchem-1645	388	23	,	,	PUNCT
eurjchem-1645	388	24	ch2	ch2	PROPN
eurjchem-1645	388	25	)	)	PUNCT
eurjchem-1645	388	26	,	,	PUNCT
eurjchem-1645	388	27	4.12	4.12	NUM
eurjchem-1645	388	28	(	(	PUNCT
eurjchem-1645	388	29	q	q	NOUN
eurjchem-1645	388	30	,	,	PUNCT
eurjchem-1645	388	31	2h	2h	NUM
eurjchem-1645	388	32	,	,	PUNCT
eurjchem-1645	388	33	j	j	PROPN
eurjchem-1645	388	34	=	=	PROPN
eurjchem-1645	388	35	8.4	8.4	NUM
eurjchem-1645	388	36	hz	hz	NOUN
eurjchem-1645	388	37	,	,	PUNCT
eurjchem-1645	388	38	ch2	ch2	PROPN
eurjchem-1645	388	39	)	)	PUNCT
eurjchem-1645	388	40	,	,	PUNCT
eurjchem-1645	388	41	4.94	4.94	NUM
eurjchem-1645	388	42	(	(	PUNCT
eurjchem-1645	388	43	s	s	PROPN
eurjchem-1645	388	44	,	,	PUNCT
eurjchem-1645	388	45	2h	2h	NUM
eurjchem-1645	388	46	,	,	PUNCT
eurjchem-1645	388	47	n‐	n‐	NOUN
eurjchem-1645	388	48	ch2	ch2	PROPN
eurjchem-1645	388	49	)	)	PUNCT
eurjchem-1645	388	50	,	,	PUNCT
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eurjchem-1645	388	52	(	(	PUNCT
eurjchem-1645	388	53	t	t	PROPN
eurjchem-1645	388	54	,	,	PUNCT
eurjchem-1645	388	55	1h	1h	NUM
eurjchem-1645	388	56	,	,	PUNCT
eurjchem-1645	388	57	j	j	PROPN
eurjchem-1645	388	58	=	=	SYM
eurjchem-1645	388	59	7.6	7.6	NUM
eurjchem-1645	388	60	hz	hz	NOUN
eurjchem-1645	388	61	,	,	PUNCT
eurjchem-1645	388	62	ar‐h	ar‐h	NOUN
eurjchem-1645	388	63	)	)	PUNCT
eurjchem-1645	388	64	,	,	PUNCT
eurjchem-1645	388	65	7.74	7.74	NUM
eurjchem-1645	388	66	(	(	PUNCT
eurjchem-1645	388	67	t	t	PROPN
eurjchem-1645	388	68	,	,	PUNCT
eurjchem-1645	388	69	1h	1h	NUM
eurjchem-1645	388	70	,	,	PUNCT
eurjchem-1645	388	71	j	j	PROPN
eurjchem-1645	388	72	=	=	SYM
eurjchem-1645	388	73	8	8	NUM
eurjchem-1645	388	74	hz	hz	NOUN
eurjchem-1645	388	75	,	,	PUNCT
eurjchem-1645	388	76	ar‐h	ar‐h	NOUN
eurjchem-1645	388	77	)	)	PUNCT
eurjchem-1645	388	78	,	,	PUNCT
eurjchem-1645	388	79	7.84	7.84	NUM
eurjchem-1645	388	80	(	(	PUNCT
eurjchem-1645	388	81	t	t	PROPN
eurjchem-1645	388	82	,	,	PUNCT
eurjchem-1645	388	83	1h	1h	NUM
eurjchem-1645	388	84	,	,	PUNCT
eurjchem-1645	388	85	j	j	PROPN
eurjchem-1645	388	86	=	=	SYM
eurjchem-1645	388	87	8	8	NUM
eurjchem-1645	388	88	hz	hz	NOUN
eurjchem-1645	388	89	,	,	PUNCT
eurjchem-1645	388	90	ar‐h	ar‐h	PROPN
eurjchem-1645	388	91	)	)	PUNCT
eurjchem-1645	388	92	,	,	PUNCT
eurjchem-1645	388	93	8.14	8.14	NUM
eurjchem-1645	388	94	(	(	PUNCT
eurjchem-1645	388	95	d	d	PROPN
eurjchem-1645	388	96	,	,	PUNCT
eurjchem-1645	388	97	1h	1h	NUM
eurjchem-1645	388	98	,	,	PUNCT
eurjchem-1645	388	99	j	j	PROPN
eurjchem-1645	388	100	=	=	SYM
eurjchem-1645	388	101	7.8	7.8	NUM
eurjchem-1645	388	102	hz	hz	NOUN
eurjchem-1645	388	103	,	,	PUNCT
eurjchem-1645	388	104	ar‐h	ar‐h	PROPN
eurjchem-1645	388	105	)	)	PUNCT
eurjchem-1645	388	106	,	,	PUNCT
eurjchem-1645	388	107	8.22	8.22	NUM
eurjchem-1645	388	108	(	(	PUNCT
eurjchem-1645	388	109	d	d	PROPN
eurjchem-1645	388	110	,	,	PUNCT
eurjchem-1645	388	111	1h	1h	NUM
eurjchem-1645	388	112	,	,	PUNCT
eurjchem-1645	388	113	j	j	PROPN
eurjchem-1645	388	114	=	=	SYM
eurjchem-1645	388	115	7.8	7.8	NUM
eurjchem-1645	388	116	hz	hz	NOUN
eurjchem-1645	388	117	,	,	PUNCT
eurjchem-1645	388	118	ar‐h	ar‐h	PROPN
eurjchem-1645	388	119	)	)	PUNCT
eurjchem-1645	388	120	,	,	PUNCT
eurjchem-1645	388	121	8.42	8.42	NUM
eurjchem-1645	388	122	(	(	PUNCT
eurjchem-1645	388	123	d	d	PROPN
eurjchem-1645	388	124	,	,	PUNCT
eurjchem-1645	388	125	1h	1h	NUM
eurjchem-1645	388	126	,	,	PUNCT
eurjchem-1645	388	127	j	j	PROPN
eurjchem-1645	388	128	=	=	SYM
eurjchem-1645	388	129	7.6	7.6	NUM
eurjchem-1645	388	130	hz	hz	NOUN
eurjchem-1645	388	131	,	,	PUNCT
eurjchem-1645	388	132	ar‐h	ar‐h	PROPN
eurjchem-1645	388	133	)	)	PUNCT
eurjchem-1645	388	134	,	,	PUNCT
eurjchem-1645	388	135	8.58	8.58	NUM
eurjchem-1645	388	136	(	(	PUNCT
eurjchem-1645	388	137	s	s	PROPN
eurjchem-1645	388	138	,	,	PUNCT
eurjchem-1645	388	139	1h	1h	NUM
eurjchem-1645	388	140	,	,	PUNCT
eurjchem-1645	388	141	ar‐h	ar‐h	NOUN
eurjchem-1645	388	142	)	)	PUNCT
eurjchem-1645	388	143	,	,	PUNCT
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eurjchem-1645	388	145	(	(	PUNCT
eurjchem-1645	388	146	br	br	NOUN
eurjchem-1645	388	147	,	,	PUNCT
eurjchem-1645	388	148	2h	2h	NUM
eurjchem-1645	388	149	,	,	PUNCT
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eurjchem-1645	388	151	&	&	CCONJ
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eurjchem-1645	388	153	(	(	PUNCT
eurjchem-1645	388	154	br	br	NOUN
eurjchem-1645	388	155	.	.	PROPN
eurjchem-1645	389	1	s	s	PART
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eurjchem-1645	389	3	1h	1h	NUM
eurjchem-1645	389	4	,	,	PUNCT
eurjchem-1645	389	5	nh	nh	PROPN
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eurjchem-1645	389	7	.	.	PUNCT
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eurjchem-1645	390	3	(	(	PUNCT
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eurjchem-1645	390	7	cdcl3	cdcl3	PROPN
eurjchem-1645	390	8	,	,	PUNCT
eurjchem-1645	390	9	δ	δ	PROPN
eurjchem-1645	390	10	,	,	PUNCT
eurjchem-1645	390	11	ppm	ppm	NOUN
eurjchem-1645	390	12	):	):	PUNCT
eurjchem-1645	390	13	12.76	12.76	NUM
eurjchem-1645	390	14	,	,	PUNCT
eurjchem-1645	390	15	49.12	49.12	NUM
eurjchem-1645	390	16	,	,	PUNCT
eurjchem-1645	390	17	52.46	52.46	NUM
eurjchem-1645	390	18	,	,	PUNCT
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eurjchem-1645	390	20	,	,	PUNCT
eurjchem-1645	390	21	110.36	110.36	NUM
eurjchem-1645	390	22	,	,	PUNCT
eurjchem-1645	390	23	128.62	128.62	NUM
eurjchem-1645	390	24	,	,	PUNCT
eurjchem-1645	390	25	128.88	128.88	NUM
eurjchem-1645	390	26	,	,	PUNCT
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eurjchem-1645	390	28	,	,	PUNCT
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eurjchem-1645	390	30	,	,	PUNCT
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eurjchem-1645	390	32	,	,	PUNCT
eurjchem-1645	390	33	130.41	130.41	NUM
eurjchem-1645	390	34	,	,	PUNCT
eurjchem-1645	390	35	134.83	134.83	NUM
eurjchem-1645	390	36	,	,	PUNCT
eurjchem-1645	390	37	144.42	144.42	NUM
eurjchem-1645	390	38	,	,	PUNCT
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eurjchem-1645	390	40	,	,	PUNCT
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eurjchem-1645	391	7	z	z	NOUN
eurjchem-1645	391	8	):	):	PUNCT
eurjchem-1645	391	9	329	329	NUM
eurjchem-1645	391	10	(	(	PUNCT
eurjchem-1645	391	11	m+h	m+h	NOUN
eurjchem-1645	391	12	)	)	PUNCT
eurjchem-1645	391	13	.	.	PUNCT
eurjchem-1645	392	1	anal	anal	PROPN
eurjchem-1645	392	2	.	.	PUNCT
eurjchem-1645	392	3	calcd	calcd	NOUN
eurjchem-1645	392	4	.	.	PUNCT
eurjchem-1645	393	1	for	for	ADP
eurjchem-1645	393	2	c19h16n6	c19h16n6	NOUN
eurjchem-1645	393	3	:	:	PUNCT
eurjchem-1645	393	4	c	c	NOUN
eurjchem-1645	393	5	,	,	PUNCT
eurjchem-1645	393	6	69.50	69.50	NUM
eurjchem-1645	393	7	;	;	PUNCT
eurjchem-1645	393	8	h	h	NOUN
eurjchem-1645	393	9	,	,	PUNCT
eurjchem-1645	393	10	4.91	4.91	NUM
eurjchem-1645	393	11	;	;	PUNCT
eurjchem-1645	393	12	n	n	CCONJ
eurjchem-1645	393	13	,	,	PUNCT
eurjchem-1645	393	14	25.59	25.59	NUM
eurjchem-1645	393	15	.	.	PUNCT
eurjchem-1645	393	16	found	find	VERB
eurjchem-1645	393	17	:	:	PUNCT
eurjchem-1645	394	1	c	c	X
eurjchem-1645	394	2	,	,	PUNCT
eurjchem-1645	394	3	69.52	69.52	NUM
eurjchem-1645	394	4	;	;	PUNCT
eurjchem-1645	395	1	h	h	NOUN
eurjchem-1645	395	2	,	,	PUNCT
eurjchem-1645	395	3	4.93	4.93	NUM
eurjchem-1645	395	4	;	;	PUNCT
eurjchem-1645	395	5	n	n	CCONJ
eurjchem-1645	395	6	,	,	PUNCT
eurjchem-1645	395	7	25.60	25.60	NUM
eurjchem-1645	395	8	%	%	NOUN
eurjchem-1645	395	9	.	.	PUNCT
eurjchem-1645	396	1	hplc	hplc	NOUN
eurjchem-1645	396	2	:	:	PUNCT
eurjchem-1645	396	3	r.t	r.t	PROPN
eurjchem-1645	396	4	.	.	PUNCT
eurjchem-1645	397	1	=	=	PROPN
eurjchem-1645	397	2	6.59	6.59	NUM
eurjchem-1645	397	3	min	min	NOUN
eurjchem-1645	397	4	,	,	PUNCT
eurjchem-1645	397	5	purity	purity	NOUN
eurjchem-1645	397	6	=	=	NUM
eurjchem-1645	397	7	95.8	95.8	NUM
eurjchem-1645	397	8	%	%	NOUN
eurjchem-1645	397	9	.	.	PUNCT
eurjchem-1645	398	1	5‐(4,5,6,7‐tetrahydro‐6‐(pyrimidin‐2‐yl)‐1h‐pyrazolo[3	5‐(4,5,6,7‐tetrahydro‐6‐(pyrimidin‐2‐yl)‐1h‐pyrazolo[3	NUM
eurjchem-1645	398	2	,	,	PUNCT
eurjchem-1645	398	3	4‐	4‐	PROPN
eurjchem-1645	398	4	c]pyridin‐3‐yl)quinolone	c]pyridin‐3‐yl)quinolone	PROPN
eurjchem-1645	398	5	(	(	PUNCT
eurjchem-1645	398	6	13h	13h	NOUN
eurjchem-1645	398	7	):	):	PUNCT
eurjchem-1645	398	8	color	color	NOUN
eurjchem-1645	398	9	:	:	PUNCT
eurjchem-1645	398	10	white	white	ADJ
eurjchem-1645	398	11	.	.	PUNCT
eurjchem-1645	399	1	yield	yield	NOUN
eurjchem-1645	399	2	:	:	PUNCT
eurjchem-1645	399	3	88	88	NUM
eurjchem-1645	399	4	%	%	NOUN
eurjchem-1645	399	5	.	.	PUNCT
eurjchem-1645	400	1	m.p	m.p	PROPN
eurjchem-1645	400	2	.	.	PROPN
eurjchem-1645	400	3	:	:	PUNCT
eurjchem-1645	400	4	188‐189	188‐189	NUM
eurjchem-1645	400	5	°	°	PROPN
eurjchem-1645	400	6	c	c	PROPN
eurjchem-1645	400	7	.	.	PUNCT
eurjchem-1645	401	1	1h	1h	NUM
eurjchem-1645	401	2	nmr	nmr	NOUN
eurjchem-1645	401	3	(	(	PUNCT
eurjchem-1645	401	4	400	400	NUM
eurjchem-1645	401	5	mhz	mhz	NOUN
eurjchem-1645	401	6	,	,	PUNCT
eurjchem-1645	401	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	401	8	,	,	PUNCT
eurjchem-1645	401	9	δ	δ	PROPN
eurjchem-1645	401	10	,	,	PUNCT
eurjchem-1645	401	11	ppm	ppm	NUM
eurjchem-1645	401	12	):	):	PUNCT
eurjchem-1645	401	13	2.62	2.62	NUM
eurjchem-1645	401	14	(	(	PUNCT
eurjchem-1645	401	15	t	t	PROPN
eurjchem-1645	401	16	,	,	PUNCT
eurjchem-1645	401	17	2h	2h	NUM
eurjchem-1645	401	18	,	,	PUNCT
eurjchem-1645	401	19	j	j	PROPN
eurjchem-1645	401	20	=	=	PROPN
eurjchem-1645	401	21	8.2	8.2	NUM
eurjchem-1645	401	22	hz	hz	NOUN
eurjchem-1645	401	23	,	,	PUNCT
eurjchem-1645	401	24	ch2	ch2	PROPN
eurjchem-1645	401	25	)	)	PUNCT
eurjchem-1645	401	26	,	,	PUNCT
eurjchem-1645	401	27	4.04	4.04	NUM
eurjchem-1645	401	28	(	(	PUNCT
eurjchem-1645	401	29	q	q	NOUN
eurjchem-1645	401	30	,	,	PUNCT
eurjchem-1645	401	31	2h	2h	NUM
eurjchem-1645	401	32	,	,	PUNCT
eurjchem-1645	401	33	j	j	PROPN
eurjchem-1645	401	34	=	=	PROPN
eurjchem-1645	401	35	8.2	8.2	NUM
eurjchem-1645	401	36	hz	hz	NOUN
eurjchem-1645	401	37	,	,	PUNCT
eurjchem-1645	401	38	ch2	ch2	PROPN
eurjchem-1645	401	39	)	)	PUNCT
eurjchem-1645	401	40	,	,	PUNCT
eurjchem-1645	401	41	4.98	4.98	NUM
eurjchem-1645	401	42	(	(	PUNCT
eurjchem-1645	401	43	s	s	PROPN
eurjchem-1645	401	44	,	,	PUNCT
eurjchem-1645	401	45	2h	2h	NUM
eurjchem-1645	401	46	,	,	PUNCT
eurjchem-1645	401	47	n‐ch2	n‐ch2	PROPN
eurjchem-1645	401	48	)	)	PUNCT
eurjchem-1645	401	49	,	,	PUNCT
eurjchem-1645	401	50	6.63	6.63	NUM
eurjchem-1645	401	51	(	(	PUNCT
eurjchem-1645	401	52	s	s	PROPN
eurjchem-1645	401	53	,	,	PUNCT
eurjchem-1645	401	54	1h	1h	NUM
eurjchem-1645	401	55	,	,	PUNCT
eurjchem-1645	401	56	ar‐h	ar‐h	NOUN
eurjchem-1645	401	57	)	)	PUNCT
eurjchem-1645	401	58	,	,	PUNCT
eurjchem-1645	401	59	7.44	7.44	NUM
eurjchem-1645	401	60	(	(	PUNCT
eurjchem-1645	401	61	br	br	PROPN
eurjchem-1645	401	62	,	,	PUNCT
eurjchem-1645	401	63	1h	1h	NUM
eurjchem-1645	401	64	,	,	PUNCT
eurjchem-1645	401	65	ar‐h	ar‐h	NOUN
eurjchem-1645	401	66	)	)	PUNCT
eurjchem-1645	401	67	,	,	PUNCT
eurjchem-1645	401	68	7.68	7.68	NUM
eurjchem-1645	401	69	(	(	PUNCT
eurjchem-1645	401	70	d	d	PROPN
eurjchem-1645	401	71	,	,	PUNCT
eurjchem-1645	401	72	1h	1h	NUM
eurjchem-1645	401	73	,	,	PUNCT
eurjchem-1645	401	74	j	j	PROPN
eurjchem-1645	401	75	=	=	SYM
eurjchem-1645	401	76	8	8	NUM
eurjchem-1645	401	77	hz	hz	NOUN
eurjchem-1645	401	78	,	,	PUNCT
eurjchem-1645	401	79	ar‐	ar‐	PROPN
eurjchem-1645	401	80	h	h	NOUN
eurjchem-1645	401	81	)	)	PUNCT
eurjchem-1645	401	82	,	,	PUNCT
eurjchem-1645	401	83	7.83‐7.68	7.83‐7.68	NUM
eurjchem-1645	401	84	(	(	PUNCT
eurjchem-1645	401	85	m	m	PROPN
eurjchem-1645	401	86	,	,	PUNCT
eurjchem-1645	401	87	2h	2h	NUM
eurjchem-1645	401	88	,	,	PUNCT
eurjchem-1645	401	89	ar‐h	ar‐h	NOUN
eurjchem-1645	401	90	)	)	PUNCT
eurjchem-1645	401	91	,	,	PUNCT
eurjchem-1645	401	92	8.23‐8.01	8.23‐8.01	NUM
eurjchem-1645	401	93	(	(	PUNCT
eurjchem-1645	401	94	m	m	PROPN
eurjchem-1645	401	95	,	,	PUNCT
eurjchem-1645	401	96	2h	2h	NUM
eurjchem-1645	401	97	,	,	PUNCT
eurjchem-1645	401	98	ar‐h	ar‐h	NOUN
eurjchem-1645	401	99	)	)	PUNCT
eurjchem-1645	401	100	,	,	PUNCT
eurjchem-1645	401	101	8.40	8.40	NUM
eurjchem-1645	401	102	(	(	PUNCT
eurjchem-1645	401	103	s	s	PROPN
eurjchem-1645	401	104	,	,	PUNCT
eurjchem-1645	401	105	1h	1h	NUM
eurjchem-1645	401	106	,	,	PUNCT
eurjchem-1645	401	107	ar‐h	ar‐h	NOUN
eurjchem-1645	401	108	)	)	PUNCT
eurjchem-1645	401	109	,	,	PUNCT
eurjchem-1645	401	110	8.92	8.92	NUM
eurjchem-1645	401	111	(	(	PUNCT
eurjchem-1645	401	112	s	s	PROPN
eurjchem-1645	401	113	,	,	PUNCT
eurjchem-1645	401	114	1h	1h	NUM
eurjchem-1645	401	115	,	,	PUNCT
eurjchem-1645	401	116	ar‐h	ar‐h	NOUN
eurjchem-1645	401	117	)	)	PUNCT
eurjchem-1645	401	118	,	,	PUNCT
eurjchem-1645	401	119	13.2	13.2	NUM
eurjchem-1645	401	120	(	(	PUNCT
eurjchem-1645	401	121	br	br	NOUN
eurjchem-1645	401	122	.	.	PUNCT
eurjchem-1645	401	123	s	s	PART
eurjchem-1645	401	124	,	,	PUNCT
eurjchem-1645	401	125	1h	1h	NUM
eurjchem-1645	401	126	,	,	PUNCT
eurjchem-1645	401	127	nh	nh	PROPN
eurjchem-1645	401	128	)	)	PUNCT
eurjchem-1645	401	129	.	.	PUNCT
eurjchem-1645	402	1	13c	13c	NOUN
eurjchem-1645	402	2	nmr	nmr	NOUN
eurjchem-1645	402	3	(	(	PUNCT
eurjchem-1645	402	4	100	100	NUM
eurjchem-1645	402	5	mhz	mhz	NOUN
eurjchem-1645	402	6	,	,	PUNCT
eurjchem-1645	402	7	cdcl3	cdcl3	PROPN
eurjchem-1645	402	8	,	,	PUNCT
eurjchem-1645	402	9	δ	δ	PROPN
eurjchem-1645	402	10	,	,	PUNCT
eurjchem-1645	402	11	ppm	ppm	NOUN
eurjchem-1645	402	12	):	):	PUNCT
eurjchem-1645	402	13	15.55	15.55	NUM
eurjchem-1645	402	14	,	,	PUNCT
eurjchem-1645	402	15	49.33	49.33	NUM
eurjchem-1645	402	16	,	,	PUNCT
eurjchem-1645	402	17	53.66	53.66	NUM
eurjchem-1645	402	18	,	,	PUNCT
eurjchem-1645	402	19	110.21	110.21	NUM
eurjchem-1645	402	20	,	,	PUNCT
eurjchem-1645	402	21	116.68	116.68	NUM
eurjchem-1645	402	22	,	,	PUNCT
eurjchem-1645	402	23	119.7	119.7	NUM
eurjchem-1645	402	24	,	,	PUNCT
eurjchem-1645	402	25	121.22	121.22	NUM
eurjchem-1645	402	26	,	,	PUNCT
eurjchem-1645	402	27	125.58	125.58	NUM
eurjchem-1645	402	28	,	,	PUNCT
eurjchem-1645	402	29	127.79	127.79	NUM
eurjchem-1645	402	30	,	,	PUNCT
eurjchem-1645	402	31	129.10	129.10	NUM
eurjchem-1645	402	32	,	,	PUNCT
eurjchem-1645	402	33	130.00	130.00	NUM
eurjchem-1645	402	34	,	,	PUNCT
eurjchem-1645	402	35	130.42	130.42	NUM
eurjchem-1645	402	36	,	,	PUNCT
eurjchem-1645	402	37	136.46	136.46	NUM
eurjchem-1645	402	38	,	,	PUNCT
eurjchem-1645	402	39	137.12	137.12	NUM
eurjchem-1645	402	40	,	,	PUNCT
eurjchem-1645	402	41	147.45	147.45	NUM
eurjchem-1645	402	42	,	,	PUNCT
eurjchem-1645	402	43	150.51	150.51	NUM
eurjchem-1645	402	44	,	,	PUNCT
eurjchem-1645	402	45	159.12	159.12	NUM
eurjchem-1645	402	46	,	,	PUNCT
eurjchem-1645	402	47	162.84	162.84	NUM
eurjchem-1645	402	48	.	.	PUNCT
eurjchem-1645	403	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	403	2	(	(	PUNCT
eurjchem-1645	403	3	ei	ei	PROPN
eurjchem-1645	403	4	,	,	PUNCT
eurjchem-1645	403	5	m	m	PROPN
eurjchem-1645	403	6	/	/	SYM
eurjchem-1645	403	7	z	z	NOUN
eurjchem-1645	403	8	):	):	PUNCT
eurjchem-1645	403	9	329	329	NUM
eurjchem-1645	403	10	(	(	PUNCT
eurjchem-1645	403	11	m+h	m+h	NOUN
eurjchem-1645	403	12	)	)	PUNCT
eurjchem-1645	403	13	.	.	PUNCT
eurjchem-1645	404	1	anal	anal	PROPN
eurjchem-1645	404	2	.	.	PUNCT
eurjchem-1645	404	3	calcd	calcd	NOUN
eurjchem-1645	404	4	.	.	PUNCT
eurjchem-1645	405	1	for	for	ADP
eurjchem-1645	405	2	c19h16n6	c19h16n6	NOUN
eurjchem-1645	405	3	:	:	PUNCT
eurjchem-1645	405	4	c	c	NOUN
eurjchem-1645	405	5	,	,	PUNCT
eurjchem-1645	405	6	69.50	69.50	NUM
eurjchem-1645	405	7	;	;	PUNCT
eurjchem-1645	405	8	h	h	NOUN
eurjchem-1645	405	9	,	,	PUNCT
eurjchem-1645	405	10	4.91	4.91	NUM
eurjchem-1645	405	11	;	;	PUNCT
eurjchem-1645	405	12	n	n	CCONJ
eurjchem-1645	405	13	,	,	PUNCT
eurjchem-1645	405	14	25.59	25.59	NUM
eurjchem-1645	405	15	.	.	PUNCT
eurjchem-1645	405	16	found	find	VERB
eurjchem-1645	405	17	:	:	PUNCT
eurjchem-1645	406	1	c	c	X
eurjchem-1645	406	2	,	,	PUNCT
eurjchem-1645	406	3	69.51	69.51	NUM
eurjchem-1645	406	4	;	;	PUNCT
eurjchem-1645	406	5	h	h	X
eurjchem-1645	406	6	,	,	PUNCT
eurjchem-1645	406	7	4.90	4.90	NUM
eurjchem-1645	406	8	;	;	PUNCT
eurjchem-1645	406	9	n	n	CCONJ
eurjchem-1645	406	10	,	,	PUNCT
eurjchem-1645	406	11	25.59	25.59	NUM
eurjchem-1645	406	12	%	%	NOUN
eurjchem-1645	406	13	.	.	PUNCT
eurjchem-1645	407	1	hplc	hplc	NOUN
eurjchem-1645	407	2	:	:	PUNCT
eurjchem-1645	407	3	r.t	r.t	PROPN
eurjchem-1645	407	4	.	.	PUNCT
eurjchem-1645	408	1	=	=	SYM
eurjchem-1645	409	1	4,78	4,78	NUM
eurjchem-1645	409	2	min	min	PROPN
eurjchem-1645	409	3	,	,	PUNCT
eurjchem-1645	409	4	purity	purity	NOUN
eurjchem-1645	409	5	=	=	NUM
eurjchem-1645	409	6	99.2	99.2	NUM
eurjchem-1645	409	7	%	%	NOUN
eurjchem-1645	409	8	.	.	PUNCT
eurjchem-1645	410	1	2.2.13	2.2.13	NUM
eurjchem-1645	410	2	.	.	PUNCT
eurjchem-1645	410	3	general	general	ADJ
eurjchem-1645	410	4	procedure	procedure	NOUN
eurjchem-1645	410	5	for	for	ADP
eurjchem-1645	410	6	synthesis	synthesis	NOUN
eurjchem-1645	410	7	of	of	ADP
eurjchem-1645	410	8	compounds	compound	NOUN
eurjchem-1645	410	9	14a‐	14a‐	NUM
eurjchem-1645	410	10	h	h	NOUN
eurjchem-1645	410	11	,	,	PUNCT
eurjchem-1645	410	12	step	step	NOUN
eurjchem-1645	410	13	(	(	PUNCT
eurjchem-1645	410	14	a	a	NOUN
eurjchem-1645	410	15	)	)	PUNCT
eurjchem-1645	410	16	to	to	ADP
eurjchem-1645	410	17	a	a	DET
eurjchem-1645	410	18	stirred	stir	VERB
eurjchem-1645	410	19	solution	solution	NOUN
eurjchem-1645	410	20	of	of	ADP
eurjchem-1645	410	21	compounds	compound	NOUN
eurjchem-1645	410	22	12a‐h	12a‐h	NOUN
eurjchem-1645	410	23	(	(	PUNCT
eurjchem-1645	410	24	1	1	NUM
eurjchem-1645	410	25	mmol	mmol	NOUN
eurjchem-1645	410	26	)	)	PUNCT
eurjchem-1645	410	27	was	be	AUX
eurjchem-1645	410	28	dissolved	dissolve	VERB
eurjchem-1645	410	29	in	in	ADP
eurjchem-1645	410	30	dcm	dcm	PROPN
eurjchem-1645	410	31	(	(	PUNCT
eurjchem-1645	410	32	10	10	NUM
eurjchem-1645	410	33	ml	ml	NOUN
eurjchem-1645	410	34	)	)	PUNCT
eurjchem-1645	410	35	.	.	PUNCT
eurjchem-1645	411	1	then	then	ADV
eurjchem-1645	411	2	added	add	VERB
eurjchem-1645	411	3	kmno4	kmno4	NOUN
eurjchem-1645	411	4	(	(	PUNCT
eurjchem-1645	411	5	2	2	NUM
eurjchem-1645	411	6	equiv	equiv	NOUN
eurjchem-1645	411	7	.	.	PUNCT
eurjchem-1645	411	8	)	)	PUNCT
eurjchem-1645	412	1	and	and	CCONJ
eurjchem-1645	412	2	18‐crown‐6	18‐crown‐6	NUM
eurjchem-1645	412	3	(	(	PUNCT
eurjchem-1645	412	4	0.5	0.5	NUM
eurjchem-1645	412	5	equiv	equiv	NOUN
eurjchem-1645	412	6	.	.	PUNCT
eurjchem-1645	412	7	)	)	PUNCT
eurjchem-1645	413	1	and	and	CCONJ
eurjchem-1645	413	2	stirred	stir	VERB
eurjchem-1645	413	3	reaction	reaction	NOUN
eurjchem-1645	413	4	mixture	mixture	NOUN
eurjchem-1645	413	5	to	to	PART
eurjchem-1645	413	6	room	room	VERB
eurjchem-1645	413	7	temperature	temperature	NOUN
eurjchem-1645	413	8	for	for	ADP
eurjchem-1645	413	9	6	6	NUM
eurjchem-1645	413	10	h.	h.	NOUN
eurjchem-1645	413	11	progress	progress	NOUN
eurjchem-1645	413	12	of	of	ADP
eurjchem-1645	413	13	reaction	reaction	NOUN
eurjchem-1645	413	14	was	be	AUX
eurjchem-1645	413	15	monitored	monitor	VERB
eurjchem-1645	413	16	by	by	ADP
eurjchem-1645	413	17	lc‐ms	lc‐ms	PRON
eurjchem-1645	413	18	for	for	ADP
eurjchem-1645	413	19	the	the	DET
eurjchem-1645	413	20	consumption	consumption	NOUN
eurjchem-1645	413	21	of	of	ADP
eurjchem-1645	413	22	starting	start	VERB
eurjchem-1645	413	23	material	material	NOUN
eurjchem-1645	413	24	.	.	PUNCT
eurjchem-1645	414	1	after	after	ADP
eurjchem-1645	414	2	comp‐	comp‐	VERB
eurjchem-1645	414	3	letion	letion	NOUN
eurjchem-1645	414	4	the	the	DET
eurjchem-1645	414	5	reaction	reaction	NOUN
eurjchem-1645	414	6	,	,	PUNCT
eurjchem-1645	414	7	the	the	DET
eurjchem-1645	414	8	reaction	reaction	NOUN
eurjchem-1645	414	9	mixture	mixture	NOUN
eurjchem-1645	414	10	was	be	AUX
eurjchem-1645	414	11	diluted	dilute	VERB
eurjchem-1645	414	12	with	with	ADP
eurjchem-1645	414	13	dcm	dcm	PROPN
eurjchem-1645	414	14	(	(	PUNCT
eurjchem-1645	414	15	10	10	NUM
eurjchem-1645	414	16	ml	ml	NOUN
eurjchem-1645	414	17	)	)	PUNCT
eurjchem-1645	414	18	and	and	CCONJ
eurjchem-1645	414	19	washed	wash	VERB
eurjchem-1645	414	20	it	it	PRON
eurjchem-1645	414	21	with	with	ADP
eurjchem-1645	414	22	water	water	NOUN
eurjchem-1645	414	23	(	(	PUNCT
eurjchem-1645	414	24	3×5	3×5	NUM
eurjchem-1645	414	25	ml	ml	NOUN
eurjchem-1645	414	26	)	)	PUNCT
eurjchem-1645	414	27	.	.	PUNCT
eurjchem-1645	415	1	separated	separate	VERB
eurjchem-1645	415	2	and	and	CCONJ
eurjchem-1645	415	3	collected	collect	VERB
eurjchem-1645	415	4	the	the	DET
eurjchem-1645	415	5	organic	organic	ADJ
eurjchem-1645	415	6	layer	layer	NOUN
eurjchem-1645	415	7	,	,	PUNCT
eurjchem-1645	415	8	washed	wash	VERB
eurjchem-1645	415	9	it	it	PRON
eurjchem-1645	415	10	with	with	ADP
eurjchem-1645	415	11	5	5	NUM
eurjchem-1645	415	12	ml	ml	NOUN
eurjchem-1645	415	13	of	of	ADP
eurjchem-1645	415	14	brine	brine	NOUN
eurjchem-1645	415	15	and	and	CCONJ
eurjchem-1645	415	16	dried	dry	VERB
eurjchem-1645	415	17	organic	organic	ADJ
eurjchem-1645	415	18	layer	layer	NOUN
eurjchem-1645	415	19	over	over	ADP
eurjchem-1645	415	20	anhydrous	anhydrous	ADJ
eurjchem-1645	415	21	na2so4	na2so4	NOUN
eurjchem-1645	415	22	and	and	CCONJ
eurjchem-1645	415	23	evaporated	evaporate	VERB
eurjchem-1645	415	24	it	it	PRON
eurjchem-1645	415	25	under	under	ADP
eurjchem-1645	415	26	reduced	reduced	ADJ
eurjchem-1645	415	27	pressure	pressure	NOUN
eurjchem-1645	415	28	to	to	PART
eurjchem-1645	415	29	obtain	obtain	VERB
eurjchem-1645	415	30	crude	crude	ADJ
eurjchem-1645	415	31	compounds	compound	NOUN
eurjchem-1645	415	32	14a‐h	14a‐h	NOUN
eurjchem-1645	415	33	as	as	ADP
eurjchem-1645	415	34	semisolid	semisolid	NOUN
eurjchem-1645	415	35	compound	compound	NOUN
eurjchem-1645	415	36	.	.	PUNCT
eurjchem-1645	416	1	the	the	DET
eurjchem-1645	416	2	crude	crude	NOUN
eurjchem-1645	416	3	obtained	obtain	VERB
eurjchem-1645	416	4	was	be	AUX
eurjchem-1645	416	5	washed	wash	VERB
eurjchem-1645	416	6	with	with	ADP
eurjchem-1645	416	7	5	5	NUM
eurjchem-1645	416	8	%	%	NOUN
eurjchem-1645	416	9	ethyl	ethyl	PROPN
eurjchem-1645	416	10	acetate	acetate	NOUN
eurjchem-1645	416	11	:	:	PUNCT
eurjchem-1645	416	12	hexane	hexane	NOUN
eurjchem-1645	416	13	,	,	PUNCT
eurjchem-1645	416	14	hexane	hexane	NOUN
eurjchem-1645	416	15	and	and	CCONJ
eurjchem-1645	416	16	diethyl	diethyl	NOUN
eurjchem-1645	416	17	ether	ether	NOUN
eurjchem-1645	416	18	to	to	PART
eurjchem-1645	416	19	obtain	obtain	VERB
eurjchem-1645	416	20	yellow	yellow	ADJ
eurjchem-1645	416	21	semisolid	semisolid	NOUN
eurjchem-1645	416	22	compound	compound	NOUN
eurjchem-1645	416	23	.	.	PUNCT
eurjchem-1645	417	1	the	the	DET
eurjchem-1645	417	2	obtained	obtain	VERB
eurjchem-1645	417	3	compound	compound	NOUN
eurjchem-1645	417	4	was	be	AUX
eurjchem-1645	417	5	crystallized	crystallize	VERB
eurjchem-1645	417	6	by	by	ADP
eurjchem-1645	417	7	using	use	VERB
eurjchem-1645	417	8	cold	cold	ADJ
eurjchem-1645	417	9	pentane	pentane	NOUN
eurjchem-1645	417	10	and	and	CCONJ
eurjchem-1645	417	11	cold	cold	ADJ
eurjchem-1645	417	12	diethyl	diethyl	NOUN
eurjchem-1645	417	13	ether	ether	NOUN
eurjchem-1645	417	14	to	to	PART
eurjchem-1645	417	15	obtain	obtain	VERB
eurjchem-1645	417	16	solid	solid	ADJ
eurjchem-1645	417	17	compounds	compound	NOUN
eurjchem-1645	417	18	14a‐h	14a‐h	NOUN
eurjchem-1645	417	19	.	.	PUNCT
eurjchem-1645	418	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	418	2	3‐(benzofuran‐2‐yl)‐4,5,6,7‐tetrahydro‐6‐(3‐met	3‐(benzofuran‐2‐yl)‐4,5,6,7‐tetrahydro‐6‐(3‐met	NUM
eurjchem-1645	418	3	hoxyphenyl)‐7‐oxopyrazolo[3,4‐c]pyridine‐1‐carboxylate	hoxyphenyl)‐7‐oxopyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	418	4	(	(	PUNCT
eurjchem-1645	418	5	14a	14a	NOUN
eurjchem-1645	418	6	):	):	PUNCT
eurjchem-1645	418	7	color	color	NOUN
eurjchem-1645	418	8	:	:	PUNCT
eurjchem-1645	418	9	brown	brown	ADJ
eurjchem-1645	418	10	.	.	PUNCT
eurjchem-1645	419	1	yield	yield	NOUN
eurjchem-1645	419	2	:	:	PUNCT
eurjchem-1645	419	3	75	75	NUM
eurjchem-1645	419	4	%	%	NOUN
eurjchem-1645	419	5	.	.	PUNCT
eurjchem-1645	420	1	m.p	m.p	PROPN
eurjchem-1645	420	2	.	.	PROPN
eurjchem-1645	420	3	:	:	PUNCT
eurjchem-1645	421	1	165‐166	165‐166	NUM
eurjchem-1645	421	2	°	°	PROPN
eurjchem-1645	421	3	c	c	PROPN
eurjchem-1645	421	4	.	.	PUNCT
eurjchem-1645	422	1	1h	1h	NUM
eurjchem-1645	422	2	nmr	nmr	NOUN
eurjchem-1645	422	3	(	(	PUNCT
eurjchem-1645	422	4	400	400	NUM
eurjchem-1645	422	5	mhz	mhz	NOUN
eurjchem-1645	422	6	,	,	PUNCT
eurjchem-1645	422	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	422	8	,	,	PUNCT
eurjchem-1645	422	9	δ	δ	PROPN
eurjchem-1645	422	10	,	,	PUNCT
eurjchem-1645	422	11	ppm	ppm	NUM
eurjchem-1645	422	12	):	):	PUNCT
eurjchem-1645	422	13	1.41	1.41	NUM
eurjchem-1645	422	14	(	(	PUNCT
eurjchem-1645	422	15	s	s	PROPN
eurjchem-1645	422	16	,	,	PUNCT
eurjchem-1645	422	17	9h	9h	NUM
eurjchem-1645	422	18	,	,	PUNCT
eurjchem-1645	422	19	t‐bu	t‐bu	NOUN
eurjchem-1645	422	20	)	)	PUNCT
eurjchem-1645	422	21	,	,	PUNCT
eurjchem-1645	422	22	3.21	3.21	NUM
eurjchem-1645	422	23	(	(	PUNCT
eurjchem-1645	422	24	t	t	PROPN
eurjchem-1645	422	25	,	,	PUNCT
eurjchem-1645	422	26	2h	2h	NUM
eurjchem-1645	422	27	,	,	PUNCT
eurjchem-1645	422	28	j	j	PROPN
eurjchem-1645	422	29	=	=	SYM
eurjchem-1645	422	30	7.6	7.6	NUM
eurjchem-1645	422	31	hz	hz	NOUN
eurjchem-1645	422	32	,	,	PUNCT
eurjchem-1645	422	33	2h	2h	NUM
eurjchem-1645	422	34	,	,	PUNCT
eurjchem-1645	422	35	ch2	ch2	PROPN
eurjchem-1645	422	36	)	)	PUNCT
eurjchem-1645	422	37	,	,	PUNCT
eurjchem-1645	422	38	3.31	3.31	NUM
eurjchem-1645	422	39	(	(	PUNCT
eurjchem-1645	422	40	s	s	PROPN
eurjchem-1645	422	41	,	,	PUNCT
eurjchem-1645	422	42	3h	3h	NUM
eurjchem-1645	422	43	,	,	PUNCT
eurjchem-1645	422	44	o‐ch3	o‐ch3	PROPN
eurjchem-1645	422	45	)	)	PUNCT
eurjchem-1645	422	46	,	,	PUNCT
eurjchem-1645	422	47	4.18	4.18	NUM
eurjchem-1645	422	48	(	(	PUNCT
eurjchem-1645	422	49	d	d	NOUN
eurjchem-1645	422	50	,	,	PUNCT
eurjchem-1645	422	51	2h	2h	NUM
eurjchem-1645	422	52	,	,	PUNCT
eurjchem-1645	422	53	j	j	PROPN
eurjchem-1645	422	54	=	=	SYM
eurjchem-1645	422	55	7.6	7.6	NUM
eurjchem-1645	422	56	hz	hz	NOUN
eurjchem-1645	422	57	,	,	PUNCT
eurjchem-1645	422	58	n‐ch2	n‐ch2	PROPN
eurjchem-1645	422	59	)	)	PUNCT
eurjchem-1645	422	60	,	,	PUNCT
eurjchem-1645	422	61	6.8	6.8	NUM
eurjchem-1645	422	62	(	(	PUNCT
eurjchem-1645	422	63	d	d	PROPN
eurjchem-1645	422	64	,	,	PUNCT
eurjchem-1645	422	65	1h	1h	NUM
eurjchem-1645	422	66	,	,	PUNCT
eurjchem-1645	422	67	j	j	PROPN
eurjchem-1645	422	68	=	=	SYM
eurjchem-1645	422	69	7.6	7.6	NUM
eurjchem-1645	422	70	hz	hz	NOUN
eurjchem-1645	422	71	,	,	PUNCT
eurjchem-1645	422	72	ar‐h	ar‐h	PROPN
eurjchem-1645	422	73	)	)	PUNCT
eurjchem-1645	422	74	,	,	PUNCT
eurjchem-1645	422	75	6.87‐6.79	6.87‐6.79	NUM
eurjchem-1645	422	76	(	(	PUNCT
eurjchem-1645	422	77	m	m	PROPN
eurjchem-1645	422	78	,	,	PUNCT
eurjchem-1645	422	79	2h	2h	NUM
eurjchem-1645	422	80	,	,	PUNCT
eurjchem-1645	422	81	ar‐h	ar‐h	NOUN
eurjchem-1645	422	82	)	)	PUNCT
eurjchem-1645	422	83	,	,	PUNCT
eurjchem-1645	422	84	7.44‐7.21	7.44‐7.21	NUM
eurjchem-1645	422	85	(	(	PUNCT
eurjchem-1645	422	86	m	m	PROPN
eurjchem-1645	422	87	4h	4h	NUM
eurjchem-1645	422	88	,	,	PUNCT
eurjchem-1645	422	89	ar‐h	ar‐h	NOUN
eurjchem-1645	422	90	)	)	PUNCT
eurjchem-1645	422	91	,	,	PUNCT
eurjchem-1645	422	92	7.76‐7.6	7.76‐7.6	NUM
eurjchem-1645	422	93	(	(	PUNCT
eurjchem-1645	422	94	m	m	PROPN
eurjchem-1645	422	95	,	,	PUNCT
eurjchem-1645	422	96	2h	2h	NUM
eurjchem-1645	422	97	,	,	PUNCT
eurjchem-1645	422	98	ar‐h	ar‐h	NOUN
eurjchem-1645	422	99	)	)	PUNCT
eurjchem-1645	422	100	.	.	PUNCT
eurjchem-1645	423	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	423	2	(	(	PUNCT
eurjchem-1645	423	3	ei	ei	X
eurjchem-1645	423	4	,	,	PUNCT
eurjchem-1645	423	5	m	m	PROPN
eurjchem-1645	423	6	/	/	SYM
eurjchem-1645	423	7	z	z	NOUN
eurjchem-1645	423	8	):	):	PUNCT
eurjchem-1645	423	9	460	460	NUM
eurjchem-1645	423	10	(	(	PUNCT
eurjchem-1645	423	11	m+h	m+h	PROPN
eurjchem-1645	423	12	)	)	PUNCT
eurjchem-1645	423	13	.	.	PUNCT
eurjchem-1645	424	1	anal	anal	PROPN
eurjchem-1645	424	2	.	.	PUNCT
eurjchem-1645	424	3	calcd	calcd	NOUN
eurjchem-1645	424	4	.	.	PUNCT
eurjchem-1645	425	1	for	for	ADP
eurjchem-1645	425	2	c26h25n3o5	c26h25n3o5	PROPN
eurjchem-1645	425	3	:	:	PUNCT
eurjchem-1645	425	4	c	c	X
eurjchem-1645	425	5	,	,	PUNCT
eurjchem-1645	425	6	67.96	67.96	NUM
eurjchem-1645	425	7	;	;	PUNCT
eurjchem-1645	425	8	h	h	NOUN
eurjchem-1645	425	9	,	,	PUNCT
eurjchem-1645	425	10	5.48	5.48	NUM
eurjchem-1645	425	11	;	;	PUNCT
eurjchem-1645	425	12	n	n	CCONJ
eurjchem-1645	425	13	,	,	PUNCT
eurjchem-1645	425	14	9.14	9.14	NUM
eurjchem-1645	425	15	.	.	PUNCT
eurjchem-1645	425	16	found	find	VERB
eurjchem-1645	425	17	:	:	PUNCT
eurjchem-1645	426	1	c	c	X
eurjchem-1645	426	2	,	,	PUNCT
eurjchem-1645	426	3	67.98	67.98	NUM
eurjchem-1645	426	4	;	;	PUNCT
eurjchem-1645	426	5	h	h	NOUN
eurjchem-1645	426	6	,	,	PUNCT
eurjchem-1645	426	7	5.47	5.47	NUM
eurjchem-1645	426	8	;	;	PUNCT
eurjchem-1645	426	9	n	n	CCONJ
eurjchem-1645	426	10	,	,	PUNCT
eurjchem-1645	426	11	9.15	9.15	NUM
eurjchem-1645	426	12	%	%	NOUN
eurjchem-1645	426	13	.	.	PUNCT
eurjchem-1645	427	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	427	2	3‐(benzo[b]thiophen‐2‐yl)‐4	3‐(benzo[b]thiophen‐2‐yl)‐4	NUM
eurjchem-1645	427	3	,	,	PUNCT
eurjchem-1645	427	4	5	5	NUM
eurjchem-1645	427	5	,	,	PUNCT
eurjchem-1645	427	6	6	6	NUM
eurjchem-1645	427	7	,	,	PUNCT
eurjchem-1645	427	8	7‐tetrahydro‐6‐	7‐tetrahydro‐6‐	PROPN
eurjchem-1645	427	9	(	(	PUNCT
eurjchem-1645	427	10	3‐methoxyphenyl)‐7‐oxopyrazolo[3,4‐c]pyridine‐1‐carboxylate	3‐methoxyphenyl)‐7‐oxopyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	427	11	(	(	PUNCT
eurjchem-1645	427	12	14b	14b	NUM
eurjchem-1645	427	13	):	):	PUNCT
eurjchem-1645	428	1	color	color	NOUN
eurjchem-1645	428	2	:	:	PUNCT
eurjchem-1645	428	3	brown	brown	ADJ
eurjchem-1645	428	4	.	.	PUNCT
eurjchem-1645	428	5	yield	yield	NOUN
eurjchem-1645	428	6	:	:	PUNCT
eurjchem-1645	428	7	77	77	NUM
eurjchem-1645	428	8	%	%	NOUN
eurjchem-1645	428	9	.	.	PUNCT
eurjchem-1645	429	1	m.p	m.p	PROPN
eurjchem-1645	429	2	.	.	PROPN
eurjchem-1645	429	3	:	:	PUNCT
eurjchem-1645	430	1	171‐172	171‐172	NUM
eurjchem-1645	430	2	°	°	SYM
eurjchem-1645	430	3	c	c	PROPN
eurjchem-1645	430	4	.	.	PUNCT
eurjchem-1645	431	1	1h	1h	NUM
eurjchem-1645	431	2	nmr	nmr	NOUN
eurjchem-1645	431	3	(	(	PUNCT
eurjchem-1645	431	4	400	400	NUM
eurjchem-1645	431	5	mhz	mhz	NOUN
eurjchem-1645	431	6	,	,	PUNCT
eurjchem-1645	431	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	431	8	,	,	PUNCT
eurjchem-1645	431	9	δ	δ	PROPN
eurjchem-1645	431	10	,	,	PUNCT
eurjchem-1645	431	11	ppm	ppm	NUM
eurjchem-1645	431	12	):	):	PUNCT
eurjchem-1645	431	13	1.41	1.41	NUM
eurjchem-1645	431	14	(	(	PUNCT
eurjchem-1645	431	15	s	s	PROPN
eurjchem-1645	431	16	,	,	PUNCT
eurjchem-1645	431	17	9h	9h	NUM
eurjchem-1645	431	18	,	,	PUNCT
eurjchem-1645	431	19	t‐bu	t‐bu	NOUN
eurjchem-1645	431	20	)	)	PUNCT
eurjchem-1645	431	21	,	,	PUNCT
eurjchem-1645	431	22	3.40	3.40	NUM
eurjchem-1645	431	23	(	(	PUNCT
eurjchem-1645	431	24	t	t	PROPN
eurjchem-1645	431	25	,	,	PUNCT
eurjchem-1645	431	26	2h	2h	NUM
eurjchem-1645	431	27	,	,	PUNCT
eurjchem-1645	431	28	j	j	PROPN
eurjchem-1645	431	29	=	=	PROPN
eurjchem-1645	431	30	8.4	8.4	NUM
eurjchem-1645	431	31	hz	hz	NOUN
eurjchem-1645	431	32	,	,	PUNCT
eurjchem-1645	431	33	ch2	ch2	PROPN
eurjchem-1645	431	34	)	)	PUNCT
eurjchem-1645	431	35	,	,	PUNCT
eurjchem-1645	431	36	3.74	3.74	NUM
eurjchem-1645	431	37	(	(	PUNCT
eurjchem-1645	431	38	s	s	PROPN
eurjchem-1645	431	39	,	,	PUNCT
eurjchem-1645	431	40	3h	3h	NUM
eurjchem-1645	431	41	,	,	PUNCT
eurjchem-1645	431	42	o‐ch3	o‐ch3	PROPN
eurjchem-1645	431	43	)	)	PUNCT
eurjchem-1645	431	44	,	,	PUNCT
eurjchem-1645	431	45	4.24	4.24	NUM
eurjchem-1645	431	46	(	(	PUNCT
eurjchem-1645	431	47	d	d	PROPN
eurjchem-1645	431	48	,	,	PUNCT
eurjchem-1645	431	49	2h	2h	NUM
eurjchem-1645	431	50	,	,	PUNCT
eurjchem-1645	431	51	j	j	PROPN
eurjchem-1645	432	1	=	=	SYM
eurjchem-1645	432	2	6.2	6.2	NUM
eurjchem-1645	432	3	hz	hz	NOUN
eurjchem-1645	432	4	,	,	PUNCT
eurjchem-1645	432	5	n‐ch2	n‐ch2	PROPN
eurjchem-1645	432	6	)	)	PUNCT
eurjchem-1645	432	7	,	,	PUNCT
eurjchem-1645	432	8	6.38	6.38	NUM
eurjchem-1645	432	9	(	(	PUNCT
eurjchem-1645	432	10	d	d	PROPN
eurjchem-1645	432	11	,	,	PUNCT
eurjchem-1645	432	12	1h	1h	NUM
eurjchem-1645	432	13	,	,	PUNCT
eurjchem-1645	432	14	j	j	PROPN
eurjchem-1645	432	15	=	=	SYM
eurjchem-1645	432	16	7.6	7.6	NUM
eurjchem-1645	432	17	hz	hz	NOUN
eurjchem-1645	432	18	,	,	PUNCT
eurjchem-1645	432	19	ar‐h	ar‐h	PROPN
eurjchem-1645	432	20	)	)	PUNCT
eurjchem-1645	432	21	,	,	PUNCT
eurjchem-1645	432	22	6.54	6.54	NUM
eurjchem-1645	432	23	(	(	PUNCT
eurjchem-1645	432	24	s	s	PROPN
eurjchem-1645	432	25	,	,	PUNCT
eurjchem-1645	432	26	1h	1h	NUM
eurjchem-1645	432	27	,	,	PUNCT
eurjchem-1645	432	28	ar‐h	ar‐h	NOUN
eurjchem-1645	432	29	)	)	PUNCT
eurjchem-1645	432	30	,	,	PUNCT
eurjchem-1645	432	31	6.63‐6.57	6.63‐6.57	NUM
eurjchem-1645	432	32	(	(	PUNCT
eurjchem-1645	432	33	m	m	PROPN
eurjchem-1645	432	34	,	,	PUNCT
eurjchem-1645	432	35	2h	2h	NUM
eurjchem-1645	432	36	,	,	PUNCT
eurjchem-1645	432	37	ar‐h	ar‐h	NOUN
eurjchem-1645	432	38	)	)	PUNCT
eurjchem-1645	432	39	,	,	PUNCT
eurjchem-1645	432	40	7.2‐7.11	7.2‐7.11	NUM
eurjchem-1645	432	41	(	(	PUNCT
eurjchem-1645	432	42	m	m	PROPN
eurjchem-1645	432	43	,	,	PUNCT
eurjchem-1645	432	44	3h	3h	NUM
eurjchem-1645	432	45	,	,	PUNCT
eurjchem-1645	432	46	ar‐h	ar‐h	NOUN
eurjchem-1645	432	47	)	)	PUNCT
eurjchem-1645	432	48	,	,	PUNCT
eurjchem-1645	432	49	7.56‐7.44	7.56‐7.44	NUM
eurjchem-1645	432	50	(	(	PUNCT
eurjchem-1645	432	51	dd	dd	NOUN
eurjchem-1645	432	52	,	,	PUNCT
eurjchem-1645	432	53	2h	2h	NUM
eurjchem-1645	432	54	,	,	PUNCT
eurjchem-1645	432	55	j	j	PROPN
eurjchem-1645	432	56	=	=	PROPN
eurjchem-1645	432	57	8.2	8.2	NUM
eurjchem-1645	432	58	hz	hz	VERB
eurjchem-1645	432	59	,	,	PUNCT
eurjchem-1645	432	60	4.1	4.1	NUM
eurjchem-1645	432	61	hz	hz	NOUN
eurjchem-1645	432	62	,	,	PUNCT
eurjchem-1645	432	63	ar‐h	ar‐h	PROPN
eurjchem-1645	432	64	)	)	PUNCT
eurjchem-1645	432	65	.	.	PUNCT
eurjchem-1645	433	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	433	2	(	(	PUNCT
eurjchem-1645	433	3	ei	ei	X
eurjchem-1645	433	4	,	,	PUNCT
eurjchem-1645	433	5	m	m	PROPN
eurjchem-1645	433	6	/	/	SYM
eurjchem-1645	434	1	z	z	NOUN
eurjchem-1645	434	2	):	):	PUNCT
eurjchem-1645	434	3	476	476	NUM
eurjchem-1645	434	4	(	(	PUNCT
eurjchem-1645	434	5	m+h	m+h	PROPN
eurjchem-1645	434	6	)	)	PUNCT
eurjchem-1645	434	7	.	.	PUNCT
eurjchem-1645	435	1	anal	anal	PROPN
eurjchem-1645	435	2	.	.	PUNCT
eurjchem-1645	435	3	calcd	calcd	NOUN
eurjchem-1645	435	4	.	.	PUNCT
eurjchem-1645	436	1	for	for	SCONJ
eurjchem-1645	436	2	c26h25n3o4s	c26h25n3o4s	NUM
eurjchem-1645	436	3	:	:	PUNCT
eurjchem-1645	436	4	c	c	NOUN
eurjchem-1645	436	5	,	,	PUNCT
eurjchem-1645	436	6	65.67	65.67	NUM
eurjchem-1645	436	7	;	;	PUNCT
eurjchem-1645	436	8	h	h	NOUN
eurjchem-1645	436	9	,	,	PUNCT
eurjchem-1645	436	10	5.30	5.30	NUM
eurjchem-1645	436	11	;	;	PUNCT
eurjchem-1645	436	12	n	n	CCONJ
eurjchem-1645	436	13	,	,	PUNCT
eurjchem-1645	436	14	8.84	8.84	NUM
eurjchem-1645	436	15	.	.	PUNCT
eurjchem-1645	436	16	found	find	VERB
eurjchem-1645	436	17	:	:	PUNCT
eurjchem-1645	437	1	c	c	X
eurjchem-1645	437	2	,	,	PUNCT
eurjchem-1645	437	3	65.65	65.65	NUM
eurjchem-1645	437	4	;	;	PUNCT
eurjchem-1645	437	5	h	h	NOUN
eurjchem-1645	437	6	,	,	PUNCT
eurjchem-1645	437	7	5.31	5.31	NUM
eurjchem-1645	437	8	;	;	PUNCT
eurjchem-1645	437	9	n	n	CCONJ
eurjchem-1645	437	10	,	,	PUNCT
eurjchem-1645	437	11	8.83	8.83	NUM
eurjchem-1645	437	12	%	%	NOUN
eurjchem-1645	437	13	.	.	PUNCT
eurjchem-1645	438	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	438	2	4	4	NUM
eurjchem-1645	438	3	,	,	PUNCT
eurjchem-1645	438	4	5	5	NUM
eurjchem-1645	438	5	,	,	PUNCT
eurjchem-1645	438	6	6	6	NUM
eurjchem-1645	438	7	,	,	PUNCT
eurjchem-1645	438	8	7‐tetrahydro‐6‐(3‐methoxyphenyl)‐7‐oxo‐	7‐tetrahydro‐6‐(3‐methoxyphenyl)‐7‐oxo‐	NUM
eurjchem-1645	438	9	3‐(quinolin‐3‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	3‐(quinolin‐3‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NUM
eurjchem-1645	438	10	(	(	PUNCT
eurjchem-1645	438	11	14c	14c	NUM
eurjchem-1645	438	12	):	):	PUNCT
eurjchem-1645	438	13	color	color	NOUN
eurjchem-1645	438	14	:	:	PUNCT
eurjchem-1645	438	15	brown	brown	ADJ
eurjchem-1645	438	16	.	.	PUNCT
eurjchem-1645	438	17	yield	yield	NOUN
eurjchem-1645	438	18	:	:	PUNCT
eurjchem-1645	438	19	78	78	NUM
eurjchem-1645	438	20	%	%	NOUN
eurjchem-1645	438	21	.	.	PUNCT
eurjchem-1645	439	1	m.p	m.p	PROPN
eurjchem-1645	439	2	.	.	PROPN
eurjchem-1645	439	3	:	:	PUNCT
eurjchem-1645	440	1	181‐182	181‐182	NUM
eurjchem-1645	440	2	°	°	NUM
eurjchem-1645	440	3	c	c	PROPN
eurjchem-1645	440	4	.	.	PUNCT
eurjchem-1645	441	1	1h	1h	NUM
eurjchem-1645	441	2	nmr	nmr	NOUN
eurjchem-1645	441	3	(	(	PUNCT
eurjchem-1645	441	4	400	400	NUM
eurjchem-1645	441	5	mhz	mhz	NOUN
eurjchem-1645	441	6	,	,	PUNCT
eurjchem-1645	441	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	441	8	,	,	PUNCT
eurjchem-1645	441	9	δ	δ	PROPN
eurjchem-1645	441	10	,	,	PUNCT
eurjchem-1645	441	11	ppm	ppm	NUM
eurjchem-1645	441	12	):	):	PUNCT
eurjchem-1645	441	13	1.41	1.41	NUM
eurjchem-1645	441	14	(	(	PUNCT
eurjchem-1645	441	15	s	s	PROPN
eurjchem-1645	441	16	,	,	PUNCT
eurjchem-1645	441	17	9h	9h	NUM
eurjchem-1645	441	18	,	,	PUNCT
eurjchem-1645	441	19	t‐bu	t‐bu	NOUN
eurjchem-1645	441	20	)	)	PUNCT
eurjchem-1645	441	21	,	,	PUNCT
eurjchem-1645	441	22	3.21	3.21	NUM
eurjchem-1645	441	23	(	(	PUNCT
eurjchem-1645	441	24	br	br	PROPN
eurjchem-1645	441	25	s	s	PROPN
eurjchem-1645	441	26	,	,	PUNCT
eurjchem-1645	441	27	2h	2h	NUM
eurjchem-1645	441	28	,	,	PUNCT
eurjchem-1645	441	29	ch2	ch2	PROPN
eurjchem-1645	441	30	)	)	PUNCT
eurjchem-1645	441	31	,	,	PUNCT
eurjchem-1645	441	32	3.83	3.83	NUM
eurjchem-1645	441	33	(	(	PUNCT
eurjchem-1645	441	34	s	s	PROPN
eurjchem-1645	441	35	,	,	PUNCT
eurjchem-1645	441	36	3h	3h	NUM
eurjchem-1645	441	37	,	,	PUNCT
eurjchem-1645	441	38	o‐ch3	o‐ch3	PROPN
eurjchem-1645	441	39	)	)	PUNCT
eurjchem-1645	441	40	,	,	PUNCT
eurjchem-1645	441	41	4.16	4.16	NUM
eurjchem-1645	441	42	(	(	PUNCT
eurjchem-1645	441	43	s	s	PROPN
eurjchem-1645	441	44	,	,	PUNCT
eurjchem-1645	441	45	2h	2h	NUM
eurjchem-1645	441	46	,	,	PUNCT
eurjchem-1645	441	47	n‐ch2	n‐ch2	PROPN
eurjchem-1645	441	48	)	)	PUNCT
eurjchem-1645	441	49	,	,	PUNCT
eurjchem-1645	441	50	6.93	6.93	NUM
eurjchem-1645	441	51	(	(	PUNCT
eurjchem-1645	441	52	d	d	PROPN
eurjchem-1645	441	53	,	,	PUNCT
eurjchem-1645	441	54	1h	1h	NUM
eurjchem-1645	441	55	,	,	PUNCT
eurjchem-1645	441	56	j	j	PROPN
eurjchem-1645	441	57	=	=	SYM
eurjchem-1645	441	58	7.8	7.8	NUM
eurjchem-1645	441	59	hz	hz	NOUN
eurjchem-1645	441	60	,	,	PUNCT
eurjchem-1645	441	61	ar‐	ar‐	PROPN
eurjchem-1645	441	62	h	h	NOUN
eurjchem-1645	441	63	)	)	PUNCT
eurjchem-1645	441	64	,	,	PUNCT
eurjchem-1645	441	65	7.12	7.12	NUM
eurjchem-1645	441	66	(	(	PUNCT
eurjchem-1645	441	67	d	d	PROPN
eurjchem-1645	441	68	,	,	PUNCT
eurjchem-1645	441	69	1h	1h	NUM
eurjchem-1645	441	70	,	,	PUNCT
eurjchem-1645	441	71	j	j	PROPN
eurjchem-1645	441	72	=	=	SYM
eurjchem-1645	441	73	8	8	NUM
eurjchem-1645	441	74	hz	hz	NOUN
eurjchem-1645	441	75	,	,	PUNCT
eurjchem-1645	441	76	ar‐h	ar‐h	NOUN
eurjchem-1645	441	77	)	)	PUNCT
eurjchem-1645	441	78	,	,	PUNCT
eurjchem-1645	441	79	7.18	7.18	NUM
eurjchem-1645	441	80	(	(	PUNCT
eurjchem-1645	441	81	s	s	PROPN
eurjchem-1645	441	82	,	,	PUNCT
eurjchem-1645	441	83	1h	1h	NUM
eurjchem-1645	441	84	,	,	PUNCT
eurjchem-1645	441	85	ar‐h	ar‐h	NOUN
eurjchem-1645	441	86	)	)	PUNCT
eurjchem-1645	441	87	,	,	PUNCT
eurjchem-1645	441	88	7.42	7.42	NUM
eurjchem-1645	441	89	(	(	PUNCT
eurjchem-1645	441	90	m	m	PROPN
eurjchem-1645	441	91	,	,	PUNCT
eurjchem-1645	441	92	1h	1h	NUM
eurjchem-1645	441	93	,	,	PUNCT
eurjchem-1645	441	94	ar‐h	ar‐h	NOUN
eurjchem-1645	441	95	)	)	PUNCT
eurjchem-1645	441	96	,	,	PUNCT
eurjchem-1645	441	97	7.58	7.58	NUM
eurjchem-1645	441	98	(	(	PUNCT
eurjchem-1645	441	99	t	t	PROPN
eurjchem-1645	441	100	,	,	PUNCT
eurjchem-1645	441	101	1h	1h	NUM
eurjchem-1645	441	102	,	,	PUNCT
eurjchem-1645	441	103	j	j	PROPN
eurjchem-1645	441	104	=	=	SYM
eurjchem-1645	441	105	7.2	7.2	NUM
eurjchem-1645	441	106	hz	hz	NOUN
eurjchem-1645	441	107	,	,	PUNCT
eurjchem-1645	441	108	ar‐h	ar‐h	PROPN
eurjchem-1645	441	109	)	)	PUNCT
eurjchem-1645	441	110	,	,	PUNCT
eurjchem-1645	441	111	7.72	7.72	NUM
eurjchem-1645	441	112	(	(	PUNCT
eurjchem-1645	441	113	t	t	PROPN
eurjchem-1645	441	114	,	,	PUNCT
eurjchem-1645	441	115	1h	1h	NUM
eurjchem-1645	441	116	,	,	PUNCT
eurjchem-1645	441	117	j	j	PROPN
eurjchem-1645	441	118	=	=	SYM
eurjchem-1645	441	119	7.2	7.2	NUM
eurjchem-1645	441	120	hz	hz	NOUN
eurjchem-1645	441	121	,	,	PUNCT
eurjchem-1645	441	122	ar‐	ar‐	PROPN
eurjchem-1645	441	123	h	h	NOUN
eurjchem-1645	441	124	)	)	PUNCT
eurjchem-1645	441	125	,	,	PUNCT
eurjchem-1645	441	126	7.84	7.84	NUM
eurjchem-1645	441	127	(	(	PUNCT
eurjchem-1645	441	128	d	d	PROPN
eurjchem-1645	441	129	,	,	PUNCT
eurjchem-1645	441	130	1h	1h	NUM
eurjchem-1645	441	131	,	,	PUNCT
eurjchem-1645	441	132	j	j	PROPN
eurjchem-1645	441	133	=	=	SYM
eurjchem-1645	441	134	7.6	7.6	NUM
eurjchem-1645	441	135	hz	hz	NOUN
eurjchem-1645	441	136	,	,	PUNCT
eurjchem-1645	441	137	ar‐h	ar‐h	PROPN
eurjchem-1645	441	138	)	)	PUNCT
eurjchem-1645	441	139	,	,	PUNCT
eurjchem-1645	441	140	8.14	8.14	NUM
eurjchem-1645	441	141	(	(	PUNCT
eurjchem-1645	441	142	d	d	PROPN
eurjchem-1645	441	143	,	,	PUNCT
eurjchem-1645	441	144	1h	1h	NUM
eurjchem-1645	441	145	,	,	PUNCT
eurjchem-1645	441	146	j	j	PROPN
eurjchem-1645	441	147	=	=	SYM
eurjchem-1645	441	148	7.6	7.6	NUM
eurjchem-1645	441	149	hz	hz	NOUN
eurjchem-1645	441	150	,	,	PUNCT
eurjchem-1645	441	151	ar‐h	ar‐h	PROPN
eurjchem-1645	441	152	)	)	PUNCT
eurjchem-1645	441	153	,	,	PUNCT
eurjchem-1645	441	154	8.56	8.56	NUM
eurjchem-1645	441	155	(	(	PUNCT
eurjchem-1645	441	156	s	s	PROPN
eurjchem-1645	441	157	,	,	PUNCT
eurjchem-1645	441	158	1h	1h	NUM
eurjchem-1645	441	159	,	,	PUNCT
eurjchem-1645	441	160	ar‐h	ar‐h	NOUN
eurjchem-1645	441	161	)	)	PUNCT
eurjchem-1645	441	162	,	,	PUNCT
eurjchem-1645	441	163	9.41	9.41	NUM
eurjchem-1645	441	164	(	(	PUNCT
eurjchem-1645	441	165	s	s	PROPN
eurjchem-1645	441	166	,	,	PUNCT
eurjchem-1645	441	167	1h	1h	NUM
eurjchem-1645	441	168	,	,	PUNCT
eurjchem-1645	441	169	ar‐h	ar‐h	NOUN
eurjchem-1645	441	170	)	)	PUNCT
eurjchem-1645	441	171	.	.	PUNCT
eurjchem-1645	442	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	442	2	(	(	PUNCT
eurjchem-1645	442	3	ei	ei	X
eurjchem-1645	442	4	,	,	PUNCT
eurjchem-1645	442	5	m	m	PROPN
eurjchem-1645	442	6	/	/	SYM
eurjchem-1645	442	7	z	z	NOUN
eurjchem-1645	442	8	):	):	PUNCT
eurjchem-1645	442	9	471	471	NUM
eurjchem-1645	442	10	(	(	PUNCT
eurjchem-1645	442	11	m+h	m+h	PROPN
eurjchem-1645	442	12	)	)	PUNCT
eurjchem-1645	442	13	.	.	PUNCT
eurjchem-1645	443	1	anal	anal	PROPN
eurjchem-1645	443	2	.	.	PUNCT
eurjchem-1645	443	3	calcd	calcd	NOUN
eurjchem-1645	443	4	.	.	PUNCT
eurjchem-1645	444	1	for	for	ADP
eurjchem-1645	444	2	c27h26n4o4	c27h26n4o4	ADV
eurjchem-1645	444	3	:	:	PUNCT
eurjchem-1645	444	4	c	c	X
eurjchem-1645	444	5	,	,	PUNCT
eurjchem-1645	444	6	68.92	68.92	NUM
eurjchem-1645	444	7	;	;	PUNCT
eurjchem-1645	444	8	h	h	X
eurjchem-1645	444	9	,	,	PUNCT
eurjchem-1645	444	10	5.57	5.57	NUM
eurjchem-1645	444	11	;	;	PUNCT
eurjchem-1645	444	12	n	n	CCONJ
eurjchem-1645	444	13	,	,	PUNCT
eurjchem-1645	444	14	11.91	11.91	NUM
eurjchem-1645	444	15	.	.	PUNCT
eurjchem-1645	444	16	found	find	VERB
eurjchem-1645	444	17	:	:	PUNCT
eurjchem-1645	445	1	c	c	X
eurjchem-1645	445	2	,	,	PUNCT
eurjchem-1645	445	3	68.91	68.91	NUM
eurjchem-1645	445	4	;	;	PUNCT
eurjchem-1645	446	1	h	h	NOUN
eurjchem-1645	446	2	,	,	PUNCT
eurjchem-1645	446	3	5.55	5.55	NUM
eurjchem-1645	446	4	;	;	PUNCT
eurjchem-1645	446	5	n	n	CCONJ
eurjchem-1645	446	6	,	,	PUNCT
eurjchem-1645	446	7	11.92	11.92	NUM
eurjchem-1645	446	8	%	%	NOUN
eurjchem-1645	446	9	.	.	PUNCT
eurjchem-1645	447	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	447	2	4	4	NUM
eurjchem-1645	447	3	,	,	PUNCT
eurjchem-1645	447	4	5	5	NUM
eurjchem-1645	447	5	,	,	PUNCT
eurjchem-1645	447	6	6	6	NUM
eurjchem-1645	447	7	,	,	PUNCT
eurjchem-1645	447	8	7‐tetrahydro‐6‐(3‐methoxyphenyl)‐7‐oxo‐	7‐tetrahydro‐6‐(3‐methoxyphenyl)‐7‐oxo‐	NUM
eurjchem-1645	447	9	3‐(quinolin‐5‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	3‐(quinolin‐5‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	NUM
eurjchem-1645	447	10	(	(	PUNCT
eurjchem-1645	447	11	14d	14d	NOUN
eurjchem-1645	447	12	):	):	PUNCT
eurjchem-1645	448	1	color	color	NOUN
eurjchem-1645	448	2	:	:	PUNCT
eurjchem-1645	448	3	brown	brown	ADJ
eurjchem-1645	448	4	.	.	PUNCT
eurjchem-1645	448	5	yield	yield	NOUN
eurjchem-1645	448	6	:	:	PUNCT
eurjchem-1645	448	7	76	76	NUM
eurjchem-1645	448	8	%	%	NOUN
eurjchem-1645	448	9	.	.	PUNCT
eurjchem-1645	449	1	m.p	m.p	PROPN
eurjchem-1645	449	2	.	.	PROPN
eurjchem-1645	449	3	:	:	PUNCT
eurjchem-1645	449	4	188‐189	188‐189	NUM
eurjchem-1645	449	5	°	°	PROPN
eurjchem-1645	449	6	c	c	PROPN
eurjchem-1645	449	7	.	.	PUNCT
eurjchem-1645	450	1	1h	1h	NUM
eurjchem-1645	450	2	nmr	nmr	NOUN
eurjchem-1645	450	3	(	(	PUNCT
eurjchem-1645	450	4	400	400	NUM
eurjchem-1645	450	5	mhz	mhz	NOUN
eurjchem-1645	450	6	,	,	PUNCT
eurjchem-1645	450	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	450	8	,	,	PUNCT
eurjchem-1645	450	9	δ	δ	PROPN
eurjchem-1645	450	10	,	,	PUNCT
eurjchem-1645	450	11	ppm	ppm	NUM
eurjchem-1645	450	12	):	):	PUNCT
eurjchem-1645	450	13	1.41	1.41	NUM
eurjchem-1645	450	14	(	(	PUNCT
eurjchem-1645	450	15	s	s	PROPN
eurjchem-1645	450	16	,	,	PUNCT
eurjchem-1645	450	17	9h	9h	NUM
eurjchem-1645	450	18	,	,	PUNCT
eurjchem-1645	450	19	t‐bu	t‐bu	NOUN
eurjchem-1645	450	20	)	)	PUNCT
eurjchem-1645	450	21	,	,	PUNCT
eurjchem-1645	450	22	3.75	3.75	NUM
eurjchem-1645	450	23	(	(	PUNCT
eurjchem-1645	450	24	s	s	PROPN
eurjchem-1645	450	25	,	,	PUNCT
eurjchem-1645	450	26	3h	3h	NUM
eurjchem-1645	450	27	,	,	PUNCT
eurjchem-1645	450	28	o‐ch3	o‐ch3	PROPN
eurjchem-1645	450	29	)	)	PUNCT
eurjchem-1645	450	30	,	,	PUNCT
eurjchem-1645	450	31	3.80	3.80	NUM
eurjchem-1645	450	32	(	(	PUNCT
eurjchem-1645	450	33	d	d	PROPN
eurjchem-1645	450	34	,	,	PUNCT
eurjchem-1645	450	35	2h	2h	NUM
eurjchem-1645	450	36	,	,	PUNCT
eurjchem-1645	450	37	j	j	PROPN
eurjchem-1645	450	38	=	=	SYM
eurjchem-1645	450	39	7.6	7.6	NUM
eurjchem-1645	450	40	hz	hz	NOUN
eurjchem-1645	450	41	,	,	PUNCT
eurjchem-1645	450	42	ch2	ch2	PROPN
eurjchem-1645	450	43	)	)	PUNCT
eurjchem-1645	450	44	,	,	PUNCT
eurjchem-1645	450	45	4.38	4.38	NUM
eurjchem-1645	450	46	(	(	PUNCT
eurjchem-1645	450	47	d	d	PROPN
eurjchem-1645	450	48	,	,	PUNCT
eurjchem-1645	450	49	2h	2h	NUM
eurjchem-1645	450	50	,	,	PUNCT
eurjchem-1645	450	51	j	j	PROPN
eurjchem-1645	450	52	=	=	SYM
eurjchem-1645	450	53	7.8	7.8	NUM
eurjchem-1645	450	54	hz	hz	NOUN
eurjchem-1645	450	55	,	,	PUNCT
eurjchem-1645	450	56	n‐ch2	n‐ch2	PROPN
eurjchem-1645	450	57	)	)	PUNCT
eurjchem-1645	450	58	,	,	PUNCT
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eurjchem-1645	450	61	t	t	PROPN
eurjchem-1645	450	62	,	,	PUNCT
eurjchem-1645	450	63	1h	1h	NUM
eurjchem-1645	450	64	,	,	PUNCT
eurjchem-1645	450	65	j	j	PROPN
eurjchem-1645	450	66	=	=	SYM
eurjchem-1645	450	67	7.6	7.6	NUM
eurjchem-1645	450	68	hz	hz	NOUN
eurjchem-1645	450	69	,	,	PUNCT
eurjchem-1645	450	70	ar‐h	ar‐h	PROPN
eurjchem-1645	450	71	)	)	PUNCT
eurjchem-1645	450	72	,	,	PUNCT
eurjchem-1645	450	73	6.68	6.68	NUM
eurjchem-1645	450	74	(	(	PUNCT
eurjchem-1645	450	75	s	s	PROPN
eurjchem-1645	450	76	,	,	PUNCT
eurjchem-1645	450	77	1h	1h	NUM
eurjchem-1645	450	78	,	,	PUNCT
eurjchem-1645	450	79	ar‐h	ar‐h	NOUN
eurjchem-1645	450	80	)	)	PUNCT
eurjchem-1645	450	81	,	,	PUNCT
eurjchem-1645	450	82	6.75	6.75	NUM
eurjchem-1645	450	83	(	(	PUNCT
eurjchem-1645	450	84	t	t	PROPN
eurjchem-1645	450	85	,	,	PUNCT
eurjchem-1645	450	86	1h	1h	NUM
eurjchem-1645	450	87	,	,	PUNCT
eurjchem-1645	450	88	j	j	PROPN
eurjchem-1645	451	1	=	=	SYM
eurjchem-1645	451	2	7.8	7.8	NUM
eurjchem-1645	451	3	hz	hz	NOUN
eurjchem-1645	451	4	,	,	PUNCT
eurjchem-1645	451	5	ar‐h	ar‐h	PROPN
eurjchem-1645	451	6	)	)	PUNCT
eurjchem-1645	451	7	,	,	PUNCT
eurjchem-1645	451	8	7.14	7.14	NUM
eurjchem-1645	451	9	(	(	PUNCT
eurjchem-1645	451	10	m	m	PROPN
eurjchem-1645	451	11	,	,	PUNCT
eurjchem-1645	451	12	1h	1h	NUM
eurjchem-1645	451	13	,	,	PUNCT
eurjchem-1645	451	14	ar‐h	ar‐h	NOUN
eurjchem-1645	451	15	)	)	PUNCT
eurjchem-1645	451	16	,	,	PUNCT
eurjchem-1645	451	17	7.88	7.88	NUM
eurjchem-1645	451	18	(	(	PUNCT
eurjchem-1645	451	19	m	m	PROPN
eurjchem-1645	451	20	,	,	PUNCT
eurjchem-1645	451	21	1h	1h	NUM
eurjchem-1645	451	22	,	,	PUNCT
eurjchem-1645	451	23	ar‐h	ar‐h	NOUN
eurjchem-1645	451	24	)	)	PUNCT
eurjchem-1645	451	25	,	,	PUNCT
eurjchem-1645	451	26	8.14‐7.98	8.14‐7.98	NUM
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eurjchem-1645	451	28	m	m	PROPN
eurjchem-1645	451	29	,	,	PUNCT
eurjchem-1645	451	30	3h	3h	NUM
eurjchem-1645	451	31	,	,	PUNCT
eurjchem-1645	451	32	ar‐h	ar‐h	NOUN
eurjchem-1645	451	33	)	)	PUNCT
eurjchem-1645	451	34	,	,	PUNCT
eurjchem-1645	451	35	8.37‐8.33	8.37‐8.33	PROPN
eurjchem-1645	451	36	(	(	PUNCT
eurjchem-1645	451	37	d	d	PROPN
eurjchem-1645	451	38	,	,	PUNCT
eurjchem-1645	451	39	1h	1h	NUM
eurjchem-1645	451	40	,	,	PUNCT
eurjchem-1645	451	41	j	j	PROPN
eurjchem-1645	451	42	=	=	SYM
eurjchem-1645	451	43	7.8	7.8	NUM
eurjchem-1645	451	44	hz	hz	NOUN
eurjchem-1645	451	45	,	,	PUNCT
eurjchem-1645	451	46	ar‐h	ar‐h	PROPN
eurjchem-1645	451	47	)	)	PUNCT
eurjchem-1645	451	48	,	,	PUNCT
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eurjchem-1645	451	50	(	(	PUNCT
eurjchem-1645	451	51	s	s	PROPN
eurjchem-1645	451	52	,	,	PUNCT
eurjchem-1645	451	53	1h	1h	NUM
eurjchem-1645	451	54	,	,	PUNCT
eurjchem-1645	451	55	ar‐h	ar‐h	NOUN
eurjchem-1645	451	56	)	)	PUNCT
eurjchem-1645	451	57	.	.	PUNCT
eurjchem-1645	452	1	lc‐	lc‐	VERB
eurjchem-1645	452	2	ms	ms	PROPN
eurjchem-1645	452	3	(	(	PUNCT
eurjchem-1645	452	4	ei	ei	PROPN
eurjchem-1645	452	5	,	,	PUNCT
eurjchem-1645	452	6	m	m	PROPN
eurjchem-1645	452	7	/	/	SYM
eurjchem-1645	452	8	z	z	NOUN
eurjchem-1645	452	9	):	):	PUNCT
eurjchem-1645	452	10	471	471	NUM
eurjchem-1645	452	11	(	(	PUNCT
eurjchem-1645	452	12	m+h	m+h	PROPN
eurjchem-1645	452	13	)	)	PUNCT
eurjchem-1645	452	14	.	.	PUNCT
eurjchem-1645	453	1	anal	anal	PROPN
eurjchem-1645	453	2	.	.	PUNCT
eurjchem-1645	453	3	calcd	calcd	NOUN
eurjchem-1645	453	4	.	.	PUNCT
eurjchem-1645	454	1	for	for	ADP
eurjchem-1645	454	2	c27h26n4o4	c27h26n4o4	ADV
eurjchem-1645	454	3	:	:	PUNCT
eurjchem-1645	454	4	c	c	X
eurjchem-1645	454	5	,	,	PUNCT
eurjchem-1645	454	6	68.92	68.92	NUM
eurjchem-1645	454	7	;	;	PUNCT
eurjchem-1645	454	8	h	h	X
eurjchem-1645	454	9	,	,	PUNCT
eurjchem-1645	454	10	5.57	5.57	NUM
eurjchem-1645	454	11	;	;	PUNCT
eurjchem-1645	454	12	n	n	CCONJ
eurjchem-1645	454	13	,	,	PUNCT
eurjchem-1645	454	14	11.91	11.91	NUM
eurjchem-1645	454	15	.	.	PUNCT
eurjchem-1645	454	16	found	find	VERB
eurjchem-1645	454	17	:	:	PUNCT
eurjchem-1645	455	1	c	c	X
eurjchem-1645	455	2	,	,	PUNCT
eurjchem-1645	455	3	68.93	68.93	NUM
eurjchem-1645	455	4	;	;	PUNCT
eurjchem-1645	455	5	h	h	NOUN
eurjchem-1645	455	6	,	,	PUNCT
eurjchem-1645	455	7	5.55	5.55	NUM
eurjchem-1645	455	8	;	;	PUNCT
eurjchem-1645	455	9	n	n	CCONJ
eurjchem-1645	455	10	,	,	PUNCT
eurjchem-1645	455	11	11.92	11.92	NUM
eurjchem-1645	455	12	%	%	NOUN
eurjchem-1645	455	13	.	.	PUNCT
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eurjchem-1645	456	2	3‐(benzofuran‐2‐yl)‐4	3‐(benzofuran‐2‐yl)‐4	NUM
eurjchem-1645	456	3	,	,	PUNCT
eurjchem-1645	456	4	5	5	NUM
eurjchem-1645	456	5	,	,	PUNCT
eurjchem-1645	456	6	6	6	NUM
eurjchem-1645	456	7	,	,	PUNCT
eurjchem-1645	456	8	7‐tetrahydro‐7‐oxo‐6‐	7‐tetrahydro‐7‐oxo‐6‐	NOUN
eurjchem-1645	456	9	(	(	PUNCT
eurjchem-1645	456	10	pyrimidin‐2‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	pyrimidin‐2‐yl)pyrazolo[3,4‐c]pyridine‐1‐carboxylate	PROPN
eurjchem-1645	456	11	(	(	PUNCT
eurjchem-1645	456	12	14e	14e	NOUN
eurjchem-1645	456	13	):	):	PUNCT
eurjchem-1645	456	14	color	color	NOUN
eurjchem-1645	456	15	:	:	PUNCT
eurjchem-1645	456	16	white	white	ADJ
eurjchem-1645	456	17	.	.	PUNCT
eurjchem-1645	456	18	yield	yield	NOUN
eurjchem-1645	456	19	:	:	PUNCT
eurjchem-1645	457	1	77	77	NUM
eurjchem-1645	457	2	%	%	NOUN
eurjchem-1645	457	3	.	.	PUNCT
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eurjchem-1645	458	2	.	.	PROPN
eurjchem-1645	458	3	:	:	PUNCT
eurjchem-1645	458	4	163‐164	163‐164	NUM
eurjchem-1645	458	5	°	°	ADP
eurjchem-1645	458	6	c	c	PROPN
eurjchem-1645	458	7	.	.	PUNCT
eurjchem-1645	459	1	1h	1h	NUM
eurjchem-1645	459	2	nmr	nmr	NOUN
eurjchem-1645	459	3	(	(	PUNCT
eurjchem-1645	459	4	400	400	NUM
eurjchem-1645	459	5	mhz	mhz	NOUN
eurjchem-1645	459	6	,	,	PUNCT
eurjchem-1645	459	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	459	8	,	,	PUNCT
eurjchem-1645	459	9	δ	δ	PROPN
eurjchem-1645	459	10	,	,	PUNCT
eurjchem-1645	459	11	ppm	ppm	NUM
eurjchem-1645	459	12	):	):	PUNCT
eurjchem-1645	459	13	1.41	1.41	NUM
eurjchem-1645	459	14	(	(	PUNCT
eurjchem-1645	459	15	s	s	PROPN
eurjchem-1645	459	16	,	,	PUNCT
eurjchem-1645	459	17	9h	9h	NUM
eurjchem-1645	459	18	,	,	PUNCT
eurjchem-1645	459	19	t‐bu	t‐bu	NOUN
eurjchem-1645	459	20	)	)	PUNCT
eurjchem-1645	459	21	,	,	PUNCT
eurjchem-1645	459	22	3.22	3.22	NUM
eurjchem-1645	459	23	(	(	PUNCT
eurjchem-1645	459	24	s	s	PROPN
eurjchem-1645	459	25	,	,	PUNCT
eurjchem-1645	459	26	2h	2h	NUM
eurjchem-1645	459	27	,	,	PUNCT
eurjchem-1645	459	28	ch2	ch2	PROPN
eurjchem-1645	459	29	)	)	PUNCT
eurjchem-1645	459	30	,	,	PUNCT
eurjchem-1645	459	31	4.24	4.24	NUM
eurjchem-1645	459	32	(	(	PUNCT
eurjchem-1645	459	33	d	d	PROPN
eurjchem-1645	459	34	,	,	PUNCT
eurjchem-1645	459	35	2h	2h	NUM
eurjchem-1645	459	36	,	,	PUNCT
eurjchem-1645	459	37	j	j	PROPN
eurjchem-1645	459	38	=	=	PROPN
eurjchem-1645	459	39	8.2	8.2	NUM
eurjchem-1645	459	40	hz	hz	NOUN
eurjchem-1645	459	41	,	,	PUNCT
eurjchem-1645	459	42	n‐ch2	n‐ch2	PROPN
eurjchem-1645	459	43	)	)	PUNCT
eurjchem-1645	459	44	,	,	PUNCT
eurjchem-1645	459	45	7.41‐7.16	7.41‐7.16	NUM
eurjchem-1645	459	46	(	(	PUNCT
eurjchem-1645	459	47	m	m	PROPN
eurjchem-1645	459	48	4h	4h	NUM
eurjchem-1645	459	49	,	,	PUNCT
eurjchem-1645	459	50	ar‐h	ar‐h	NOUN
eurjchem-1645	459	51	)	)	PUNCT
eurjchem-1645	459	52	,	,	PUNCT
eurjchem-1645	459	53	7.68‐7.54	7.68‐7.54	NUM
eurjchem-1645	459	54	(	(	PUNCT
eurjchem-1645	459	55	m	m	PROPN
eurjchem-1645	459	56	,	,	PUNCT
eurjchem-1645	459	57	2h	2h	NUM
eurjchem-1645	459	58	,	,	PUNCT
eurjchem-1645	459	59	ar‐h	ar‐h	NOUN
eurjchem-1645	459	60	)	)	PUNCT
eurjchem-1645	459	61	,	,	PUNCT
eurjchem-1645	459	62	8.84	8.84	NUM
eurjchem-1645	459	63	(	(	PUNCT
eurjchem-1645	459	64	d	d	PROPN
eurjchem-1645	459	65	,	,	PUNCT
eurjchem-1645	459	66	2h	2h	NUM
eurjchem-1645	459	67	,	,	PUNCT
eurjchem-1645	459	68	j	j	PROPN
eurjchem-1645	459	69	=	=	SYM
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eurjchem-1645	459	71	hz	hz	NOUN
eurjchem-1645	459	72	,	,	PUNCT
eurjchem-1645	459	73	ar‐h	ar‐h	PROPN
eurjchem-1645	459	74	)	)	PUNCT
eurjchem-1645	459	75	.	.	PUNCT
eurjchem-1645	460	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	460	2	(	(	PUNCT
eurjchem-1645	460	3	ei	ei	X
eurjchem-1645	460	4	,	,	PUNCT
eurjchem-1645	460	5	m	m	PROPN
eurjchem-1645	460	6	/	/	SYM
eurjchem-1645	460	7	z	z	NOUN
eurjchem-1645	460	8	):	):	PUNCT
eurjchem-1645	460	9	431	431	NUM
eurjchem-1645	460	10	(	(	PUNCT
eurjchem-1645	460	11	m+h	m+h	NOUN
eurjchem-1645	460	12	)	)	PUNCT
eurjchem-1645	460	13	.	.	PUNCT
eurjchem-1645	461	1	anal	anal	PROPN
eurjchem-1645	461	2	.	.	PUNCT
eurjchem-1645	461	3	calcd	calcd	NOUN
eurjchem-1645	461	4	.	.	PUNCT
eurjchem-1645	462	1	for	for	ADP
eurjchem-1645	462	2	c23h21n5o4	c23h21n5o4	PROPN
eurjchem-1645	462	3	:	:	PUNCT
eurjchem-1645	462	4	c	c	NOUN
eurjchem-1645	462	5	,	,	PUNCT
eurjchem-1645	462	6	64.03	64.03	NUM
eurjchem-1645	462	7	;	;	PUNCT
eurjchem-1645	462	8	h	h	X
eurjchem-1645	462	9	,	,	PUNCT
eurjchem-1645	462	10	4.91	4.91	NUM
eurjchem-1645	462	11	;	;	PUNCT
eurjchem-1645	462	12	n	n	CCONJ
eurjchem-1645	462	13	,	,	PUNCT
eurjchem-1645	462	14	16.23	16.23	NUM
eurjchem-1645	462	15	.	.	PUNCT
eurjchem-1645	462	16	found	find	VERB
eurjchem-1645	462	17	:	:	PUNCT
eurjchem-1645	463	1	c	c	X
eurjchem-1645	463	2	,	,	PUNCT
eurjchem-1645	463	3	64.02	64.02	NUM
eurjchem-1645	463	4	;	;	PUNCT
eurjchem-1645	463	5	h	h	NOUN
eurjchem-1645	463	6	,	,	PUNCT
eurjchem-1645	463	7	4.94	4.94	NUM
eurjchem-1645	463	8	;	;	PUNCT
eurjchem-1645	463	9	n	n	CCONJ
eurjchem-1645	463	10	,	,	PUNCT
eurjchem-1645	463	11	16.25	16.25	NUM
eurjchem-1645	463	12	%	%	NOUN
eurjchem-1645	463	13	.	.	PUNCT
eurjchem-1645	464	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	464	2	3‐(benzo[b]thiophen‐2‐yl)‐4	3‐(benzo[b]thiophen‐2‐yl)‐4	NUM
eurjchem-1645	464	3	,	,	PUNCT
eurjchem-1645	464	4	5	5	NUM
eurjchem-1645	464	5	,	,	PUNCT
eurjchem-1645	464	6	6	6	NUM
eurjchem-1645	464	7	,	,	PUNCT
eurjchem-1645	464	8	7‐tetrahydro‐7‐	7‐tetrahydro‐7‐	PROPN
eurjchem-1645	464	9	oxo‐6‐(pyrimidin‐2‐yl)pyrazolo[3	oxo‐6‐(pyrimidin‐2‐yl)pyrazolo[3	NOUN
eurjchem-1645	464	10	,	,	PUNCT
eurjchem-1645	464	11	4‐c]pyridine‐1‐carboxylate	4‐c]pyridine‐1‐carboxylate	PROPN
eurjchem-1645	464	12	(	(	PUNCT
eurjchem-1645	464	13	14f	14f	NUM
eurjchem-1645	464	14	):	):	PUNCT
eurjchem-1645	464	15	color	color	NOUN
eurjchem-1645	464	16	:	:	PUNCT
eurjchem-1645	464	17	brown	brown	ADJ
eurjchem-1645	464	18	.	.	PUNCT
eurjchem-1645	465	1	yield	yield	NOUN
eurjchem-1645	465	2	:	:	PUNCT
eurjchem-1645	465	3	71	71	NUM
eurjchem-1645	465	4	%	%	NOUN
eurjchem-1645	465	5	.	.	PUNCT
eurjchem-1645	466	1	m.p	m.p	PROPN
eurjchem-1645	466	2	.	.	PROPN
eurjchem-1645	466	3	:	:	PUNCT
eurjchem-1645	467	1	155‐156	155‐156	NUM
eurjchem-1645	467	2	°	°	PROPN
eurjchem-1645	467	3	c	c	X
eurjchem-1645	467	4	.	.	PUNCT
eurjchem-1645	467	5	1h	1h	NUM
eurjchem-1645	467	6	nmr	nmr	NOUN
eurjchem-1645	467	7	(	(	PUNCT
eurjchem-1645	467	8	400	400	NUM
eurjchem-1645	467	9	mhz	mhz	NOUN
eurjchem-1645	467	10	,	,	PUNCT
eurjchem-1645	467	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	467	12	,	,	PUNCT
eurjchem-1645	467	13	δ	δ	PROPN
eurjchem-1645	467	14	,	,	PUNCT
eurjchem-1645	467	15	ppm	ppm	NUM
eurjchem-1645	467	16	):	):	PUNCT
eurjchem-1645	467	17	1.41	1.41	NUM
eurjchem-1645	467	18	(	(	PUNCT
eurjchem-1645	467	19	s	s	PROPN
eurjchem-1645	467	20	,	,	PUNCT
eurjchem-1645	467	21	9h	9h	NUM
eurjchem-1645	467	22	,	,	PUNCT
eurjchem-1645	467	23	t‐bu	t‐bu	NOUN
eurjchem-1645	467	24	)	)	PUNCT
eurjchem-1645	467	25	,	,	PUNCT
eurjchem-1645	467	26	3.48	3.48	NUM
eurjchem-1645	467	27	(	(	PUNCT
eurjchem-1645	467	28	s	s	PROPN
eurjchem-1645	467	29	,	,	PUNCT
eurjchem-1645	467	30	2h	2h	NUM
eurjchem-1645	467	31	,	,	PUNCT
eurjchem-1645	467	32	ch2	ch2	PROPN
eurjchem-1645	467	33	)	)	PUNCT
eurjchem-1645	467	34	,	,	PUNCT
eurjchem-1645	467	35	4.44	4.44	NUM
eurjchem-1645	467	36	(	(	PUNCT
eurjchem-1645	467	37	d	d	PROPN
eurjchem-1645	467	38	,	,	PUNCT
eurjchem-1645	467	39	2h	2h	NUM
eurjchem-1645	467	40	,	,	PUNCT
eurjchem-1645	467	41	j	j	PROPN
eurjchem-1645	467	42	=	=	PROPN
eurjchem-1645	467	43	8.2	8.2	NUM
eurjchem-1645	467	44	hz	hz	NOUN
eurjchem-1645	467	45	,	,	PUNCT
eurjchem-1645	467	46	n‐ch2	n‐ch2	PROPN
eurjchem-1645	467	47	)	)	PUNCT
eurjchem-1645	467	48	,	,	PUNCT
eurjchem-1645	467	49	7.48‐7.16	7.48‐7.16	NUM
eurjchem-1645	467	50	(	(	PUNCT
eurjchem-1645	467	51	m	m	PROPN
eurjchem-1645	467	52	4h	4h	NUM
eurjchem-1645	467	53	,	,	PUNCT
eurjchem-1645	467	54	ar‐h	ar‐h	NOUN
eurjchem-1645	467	55	)	)	PUNCT
eurjchem-1645	467	56	,	,	PUNCT
eurjchem-1645	467	57	7.78‐7.58	7.78‐7.58	NUM
eurjchem-1645	467	58	(	(	PUNCT
eurjchem-1645	467	59	m	m	PROPN
eurjchem-1645	467	60	,	,	PUNCT
eurjchem-1645	467	61	2h	2h	NUM
eurjchem-1645	467	62	,	,	PUNCT
eurjchem-1645	467	63	ar‐h	ar‐h	NOUN
eurjchem-1645	467	64	)	)	PUNCT
eurjchem-1645	467	65	,	,	PUNCT
eurjchem-1645	467	66	8.84	8.84	NUM
eurjchem-1645	467	67	(	(	PUNCT
eurjchem-1645	467	68	d	d	PROPN
eurjchem-1645	467	69	,	,	PUNCT
eurjchem-1645	467	70	2h	2h	NUM
eurjchem-1645	467	71	,	,	PUNCT
eurjchem-1645	467	72	j	j	PROPN
eurjchem-1645	467	73	=	=	SYM
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eurjchem-1645	467	75	hz	hz	NOUN
eurjchem-1645	467	76	,	,	PUNCT
eurjchem-1645	467	77	ar‐h	ar‐h	PROPN
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eurjchem-1645	467	79	.	.	PUNCT
eurjchem-1645	468	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	468	2	(	(	PUNCT
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eurjchem-1645	468	4	,	,	PUNCT
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eurjchem-1645	468	7	z	z	NOUN
eurjchem-1645	468	8	):	):	PUNCT
eurjchem-1645	468	9	448	448	NUM
eurjchem-1645	468	10	(	(	PUNCT
eurjchem-1645	468	11	m+h	m+h	NOUN
eurjchem-1645	468	12	)	)	PUNCT
eurjchem-1645	468	13	.	.	PUNCT
eurjchem-1645	469	1	anal	anal	PROPN
eurjchem-1645	469	2	.	.	PUNCT
eurjchem-1645	469	3	calcd	calcd	NOUN
eurjchem-1645	469	4	.	.	PUNCT
eurjchem-1645	470	1	for	for	ADP
eurjchem-1645	470	2	c23h21n5o3s	c23h21n5o3s	NUM
eurjchem-1645	470	3	:	:	PUNCT
eurjchem-1645	470	4	c	c	X
eurjchem-1645	470	5	,	,	PUNCT
eurjchem-1645	470	6	61.73	61.73	NUM
eurjchem-1645	470	7	;	;	PUNCT
eurjchem-1645	470	8	h	h	NOUN
eurjchem-1645	470	9	,	,	PUNCT
eurjchem-1645	470	10	4.73	4.73	NUM
eurjchem-1645	470	11	;	;	PUNCT
eurjchem-1645	470	12	n	n	CCONJ
eurjchem-1645	470	13	,	,	PUNCT
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eurjchem-1645	470	15	.	.	PUNCT
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eurjchem-1645	470	17	:	:	PUNCT
eurjchem-1645	471	1	c	c	X
eurjchem-1645	471	2	,	,	PUNCT
eurjchem-1645	471	3	61.72	61.72	NUM
eurjchem-1645	471	4	;	;	PUNCT
eurjchem-1645	471	5	h	h	NOUN
eurjchem-1645	471	6	,	,	PUNCT
eurjchem-1645	471	7	4.75	4.75	NUM
eurjchem-1645	471	8	;	;	PUNCT
eurjchem-1645	471	9	n	n	CCONJ
eurjchem-1645	471	10	,	,	PUNCT
eurjchem-1645	471	11	15.63	15.63	NUM
eurjchem-1645	471	12	%	%	NOUN
eurjchem-1645	471	13	.	.	PUNCT
eurjchem-1645	472	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	472	2	4	4	NUM
eurjchem-1645	472	3	,	,	PUNCT
eurjchem-1645	472	4	5	5	NUM
eurjchem-1645	472	5	,	,	PUNCT
eurjchem-1645	472	6	6	6	NUM
eurjchem-1645	472	7	,	,	PUNCT
eurjchem-1645	472	8	7‐tetrahydro‐7‐oxo‐6‐(pyrimidin‐2‐yl)‐3‐	7‐tetrahydro‐7‐oxo‐6‐(pyrimidin‐2‐yl)‐3‐	NUM
eurjchem-1645	472	9	(	(	PUNCT
eurjchem-1645	472	10	quinolin‐3‐yl)pyrazolo[3	quinolin‐3‐yl)pyrazolo[3	NOUN
eurjchem-1645	472	11	,	,	PUNCT
eurjchem-1645	472	12	4‐c]pyridine‐1‐carboxylate	4‐c]pyridine‐1‐carboxylate	PROPN
eurjchem-1645	472	13	(	(	PUNCT
eurjchem-1645	472	14	14	14	NUM
eurjchem-1645	472	15	g	g	NOUN
eurjchem-1645	472	16	):	):	PUNCT
eurjchem-1645	473	1	color	color	NOUN
eurjchem-1645	473	2	:	:	PUNCT
eurjchem-1645	473	3	brown	brown	ADJ
eurjchem-1645	473	4	.	.	PUNCT
eurjchem-1645	473	5	yield	yield	NOUN
eurjchem-1645	473	6	:	:	PUNCT
eurjchem-1645	473	7	76	76	NUM
eurjchem-1645	473	8	%	%	NOUN
eurjchem-1645	473	9	.	.	PUNCT
eurjchem-1645	474	1	m.p	m.p	PROPN
eurjchem-1645	474	2	.	.	PROPN
eurjchem-1645	474	3	:	:	PUNCT
eurjchem-1645	475	1	161‐162	161‐162	NUM
eurjchem-1645	475	2	°	°	SYM
eurjchem-1645	475	3	c	c	X
eurjchem-1645	475	4	.	.	PUNCT
eurjchem-1645	476	1	1h	1h	NUM
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eurjchem-1645	476	3	(	(	PUNCT
eurjchem-1645	476	4	400	400	NUM
eurjchem-1645	476	5	mhz	mhz	NOUN
eurjchem-1645	476	6	,	,	PUNCT
eurjchem-1645	476	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	476	8	,	,	PUNCT
eurjchem-1645	476	9	δ	δ	PROPN
eurjchem-1645	476	10	,	,	PUNCT
eurjchem-1645	476	11	ppm	ppm	NUM
eurjchem-1645	476	12	):	):	PUNCT
eurjchem-1645	476	13	1.41	1.41	NUM
eurjchem-1645	476	14	(	(	PUNCT
eurjchem-1645	476	15	s	s	PROPN
eurjchem-1645	476	16	,	,	PUNCT
eurjchem-1645	476	17	9h	9h	NUM
eurjchem-1645	476	18	,	,	PUNCT
eurjchem-1645	476	19	t‐bu	t‐bu	NOUN
eurjchem-1645	476	20	)	)	PUNCT
eurjchem-1645	476	21	,	,	PUNCT
eurjchem-1645	476	22	3.26	3.26	NUM
eurjchem-1645	476	23	(	(	PUNCT
eurjchem-1645	476	24	q	q	NOUN
eurjchem-1645	476	25	,	,	PUNCT
eurjchem-1645	476	26	2h	2h	NUM
eurjchem-1645	476	27	,	,	PUNCT
eurjchem-1645	476	28	j	j	PROPN
eurjchem-1645	476	29	=	=	SYM
eurjchem-1645	476	30	7.6	7.6	NUM
eurjchem-1645	476	31	hz	hz	NOUN
eurjchem-1645	476	32	,	,	PUNCT
eurjchem-1645	476	33	ch2	ch2	PROPN
eurjchem-1645	476	34	)	)	PUNCT
eurjchem-1645	476	35	,	,	PUNCT
eurjchem-1645	476	36	4.26	4.26	NUM
eurjchem-1645	476	37	(	(	PUNCT
eurjchem-1645	476	38	t	t	PROPN
eurjchem-1645	476	39	,	,	PUNCT
eurjchem-1645	476	40	2h	2h	NUM
eurjchem-1645	476	41	,	,	PUNCT
eurjchem-1645	476	42	j	j	PROPN
eurjchem-1645	476	43	=	=	SYM
eurjchem-1645	476	44	7.6	7.6	NUM
eurjchem-1645	476	45	hz	hz	NOUN
eurjchem-1645	476	46	,	,	PUNCT
eurjchem-1645	476	47	n‐ch2	n‐ch2	PROPN
eurjchem-1645	476	48	)	)	PUNCT
eurjchem-1645	476	49	,	,	PUNCT
eurjchem-1645	476	50	7.28	7.28	NUM
eurjchem-1645	476	51	(	(	PUNCT
eurjchem-1645	476	52	t	t	PROPN
eurjchem-1645	476	53	,	,	PUNCT
eurjchem-1645	476	54	1h	1h	NUM
eurjchem-1645	476	55	,	,	PUNCT
eurjchem-1645	476	56	j	j	PROPN
eurjchem-1645	476	57	=	=	SYM
eurjchem-1645	476	58	7.6	7.6	NUM
eurjchem-1645	476	59	hz	hz	NOUN
eurjchem-1645	476	60	,	,	PUNCT
eurjchem-1645	476	61	ar‐h	ar‐h	PROPN
eurjchem-1645	476	62	)	)	PUNCT
eurjchem-1645	476	63	,	,	PUNCT
eurjchem-1645	476	64	7.56	7.56	NUM
eurjchem-1645	476	65	(	(	PUNCT
eurjchem-1645	476	66	q	q	NOUN
eurjchem-1645	476	67	,	,	PUNCT
eurjchem-1645	476	68	1h	1h	NUM
eurjchem-1645	476	69	,	,	PUNCT
eurjchem-1645	476	70	j	j	PROPN
eurjchem-1645	476	71	=	=	PROPN
eurjchem-1645	476	72	8.2	8.2	NUM
eurjchem-1645	476	73	hz	hz	ADJ
eurjchem-1645	476	74	,	,	PUNCT
eurjchem-1645	476	75	ar‐h	ar‐h	NOUN
eurjchem-1645	476	76	)	)	PUNCT
eurjchem-1645	476	77	,	,	PUNCT
eurjchem-1645	476	78	7.82	7.82	NUM
eurjchem-1645	476	79	(	(	PUNCT
eurjchem-1645	476	80	t	t	PROPN
eurjchem-1645	476	81	,	,	PUNCT
eurjchem-1645	476	82	1h	1h	NUM
eurjchem-1645	476	83	,	,	PUNCT
eurjchem-1645	476	84	j	j	PROPN
eurjchem-1645	476	85	=	=	PROPN
eurjchem-1645	476	86	8.2	8.2	NUM
eurjchem-1645	476	87	hz	hz	NOUN
eurjchem-1645	476	88	,	,	PUNCT
eurjchem-1645	476	89	ar‐	ar‐	NOUN
eurjchem-1645	476	90	406	406	NUM
eurjchem-1645	476	91	pawar	pawar	NOUN
eurjchem-1645	476	92	et	et	PROPN
eurjchem-1645	476	93	al	al	PROPN
eurjchem-1645	476	94	.	.	PUNCT
eurjchem-1645	476	95	/	/	SYM
eurjchem-1645	476	96	european	european	PROPN
eurjchem-1645	476	97	journal	journal	PROPN
eurjchem-1645	476	98	of	of	ADP
eurjchem-1645	476	99	chemistry	chemistry	NOUN
eurjchem-1645	476	100	8	8	NUM
eurjchem-1645	476	101	(	(	PUNCT
eurjchem-1645	476	102	4	4	NUM
eurjchem-1645	476	103	)	)	PUNCT
eurjchem-1645	476	104	(	(	PUNCT
eurjchem-1645	476	105	2017	2017	NUM
eurjchem-1645	476	106	)	)	PUNCT
eurjchem-1645	476	107	400‐409	400‐409	NUM
eurjchem-1645	476	108	h	h	NOUN
eurjchem-1645	476	109	)	)	PUNCT
eurjchem-1645	476	110	,	,	PUNCT
eurjchem-1645	476	111	8.18‐8.02	8.18‐8.02	NUM
eurjchem-1645	476	112	(	(	PUNCT
eurjchem-1645	476	113	q	q	NOUN
eurjchem-1645	476	114	,	,	PUNCT
eurjchem-1645	476	115	2h	2h	NUM
eurjchem-1645	476	116	,	,	PUNCT
eurjchem-1645	476	117	ar‐h	ar‐h	NOUN
eurjchem-1645	476	118	)	)	PUNCT
eurjchem-1645	476	119	,	,	PUNCT
eurjchem-1645	476	120	8.60	8.60	NUM
eurjchem-1645	476	121	(	(	PUNCT
eurjchem-1645	476	122	s	s	PROPN
eurjchem-1645	476	123	,	,	PUNCT
eurjchem-1645	476	124	1h	1h	NUM
eurjchem-1645	476	125	,	,	PUNCT
eurjchem-1645	476	126	ar‐h	ar‐h	NOUN
eurjchem-1645	476	127	)	)	PUNCT
eurjchem-1645	476	128	,	,	PUNCT
eurjchem-1645	476	129	8.83	8.83	NUM
eurjchem-1645	476	130	(	(	PUNCT
eurjchem-1645	476	131	d	d	NOUN
eurjchem-1645	476	132	,	,	PUNCT
eurjchem-1645	476	133	2h	2h	NUM
eurjchem-1645	476	134	,	,	PUNCT
eurjchem-1645	476	135	ar‐	ar‐	PROPN
eurjchem-1645	476	136	h	h	NOUN
eurjchem-1645	476	137	)	)	PUNCT
eurjchem-1645	476	138	,	,	PUNCT
eurjchem-1645	476	139	9.38	9.38	NUM
eurjchem-1645	476	140	(	(	PUNCT
eurjchem-1645	476	141	s	s	PROPN
eurjchem-1645	476	142	,	,	PUNCT
eurjchem-1645	476	143	1h	1h	NUM
eurjchem-1645	476	144	,	,	PUNCT
eurjchem-1645	476	145	ar‐h	ar‐h	NOUN
eurjchem-1645	476	146	)	)	PUNCT
eurjchem-1645	476	147	.	.	PUNCT
eurjchem-1645	477	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	477	2	(	(	PUNCT
eurjchem-1645	477	3	ei	ei	X
eurjchem-1645	477	4	,	,	PUNCT
eurjchem-1645	477	5	m	m	PROPN
eurjchem-1645	477	6	/	/	SYM
eurjchem-1645	477	7	z	z	NOUN
eurjchem-1645	477	8	):	):	PUNCT
eurjchem-1645	477	9	443	443	NUM
eurjchem-1645	477	10	(	(	PUNCT
eurjchem-1645	477	11	m+h	m+h	NOUN
eurjchem-1645	477	12	)	)	PUNCT
eurjchem-1645	477	13	.	.	PUNCT
eurjchem-1645	478	1	anal	anal	PROPN
eurjchem-1645	478	2	.	.	PUNCT
eurjchem-1645	478	3	calcd	calcd	NOUN
eurjchem-1645	478	4	.	.	PUNCT
eurjchem-1645	479	1	for	for	SCONJ
eurjchem-1645	479	2	c24h22n6o3	c24h22n6o3	PROPN
eurjchem-1645	479	3	:	:	PUNCT
eurjchem-1645	479	4	c	c	X
eurjchem-1645	479	5	,	,	PUNCT
eurjchem-1645	479	6	65.15	65.15	NUM
eurjchem-1645	479	7	;	;	PUNCT
eurjchem-1645	479	8	h	h	NOUN
eurjchem-1645	479	9	,	,	PUNCT
eurjchem-1645	479	10	5.01	5.01	NUM
eurjchem-1645	479	11	;	;	PUNCT
eurjchem-1645	479	12	n	n	CCONJ
eurjchem-1645	479	13	,	,	PUNCT
eurjchem-1645	479	14	18.99	18.99	NUM
eurjchem-1645	479	15	.	.	PUNCT
eurjchem-1645	479	16	found	find	VERB
eurjchem-1645	479	17	:	:	PUNCT
eurjchem-1645	480	1	c	c	X
eurjchem-1645	480	2	,	,	PUNCT
eurjchem-1645	480	3	65.14	65.14	NUM
eurjchem-1645	480	4	;	;	PUNCT
eurjchem-1645	480	5	h	h	NOUN
eurjchem-1645	480	6	,	,	PUNCT
eurjchem-1645	480	7	5.03	5.03	NUM
eurjchem-1645	480	8	;	;	PUNCT
eurjchem-1645	480	9	n	n	CCONJ
eurjchem-1645	480	10	,	,	PUNCT
eurjchem-1645	480	11	18.98	18.98	NUM
eurjchem-1645	480	12	%	%	NOUN
eurjchem-1645	480	13	.	.	PUNCT
eurjchem-1645	481	1	tert‐butyl	tert‐butyl	ADP
eurjchem-1645	481	2	4	4	NUM
eurjchem-1645	481	3	,	,	PUNCT
eurjchem-1645	481	4	5	5	NUM
eurjchem-1645	481	5	,	,	PUNCT
eurjchem-1645	481	6	6	6	NUM
eurjchem-1645	481	7	,	,	PUNCT
eurjchem-1645	481	8	7‐tetrahydro‐7‐oxo‐6‐(pyrimidin‐2‐yl)‐3‐	7‐tetrahydro‐7‐oxo‐6‐(pyrimidin‐2‐yl)‐3‐	NUM
eurjchem-1645	481	9	(	(	PUNCT
eurjchem-1645	481	10	quinolin‐5‐yl)pyrazolo[3	quinolin‐5‐yl)pyrazolo[3	INTJ
eurjchem-1645	481	11	,	,	PUNCT
eurjchem-1645	481	12	4‐c]pyridine‐1‐carboxylate	4‐c]pyridine‐1‐carboxylate	PROPN
eurjchem-1645	481	13	(	(	PUNCT
eurjchem-1645	481	14	14h	14h	NUM
eurjchem-1645	481	15	):	):	PUNCT
eurjchem-1645	482	1	color	color	NOUN
eurjchem-1645	482	2	:	:	PUNCT
eurjchem-1645	482	3	brown	brown	ADJ
eurjchem-1645	482	4	.	.	PUNCT
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eurjchem-1645	482	6	:	:	PUNCT
eurjchem-1645	482	7	73	73	NUM
eurjchem-1645	482	8	%	%	NOUN
eurjchem-1645	482	9	.	.	PUNCT
eurjchem-1645	483	1	m.p	m.p	PROPN
eurjchem-1645	483	2	.	.	PROPN
eurjchem-1645	483	3	:	:	PUNCT
eurjchem-1645	484	1	164‐165	164‐165	NUM
eurjchem-1645	484	2	°	°	PROPN
eurjchem-1645	484	3	c	c	PROPN
eurjchem-1645	484	4	.	.	PUNCT
eurjchem-1645	484	5	1h	1h	NUM
eurjchem-1645	484	6	nmr	nmr	NOUN
eurjchem-1645	484	7	(	(	PUNCT
eurjchem-1645	484	8	400	400	NUM
eurjchem-1645	484	9	mhz	mhz	NOUN
eurjchem-1645	484	10	,	,	PUNCT
eurjchem-1645	484	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	484	12	,	,	PUNCT
eurjchem-1645	484	13	δ	δ	PROPN
eurjchem-1645	484	14	,	,	PUNCT
eurjchem-1645	484	15	ppm	ppm	NUM
eurjchem-1645	484	16	):	):	PUNCT
eurjchem-1645	484	17	1.41	1.41	NUM
eurjchem-1645	484	18	(	(	PUNCT
eurjchem-1645	484	19	s	s	PROPN
eurjchem-1645	484	20	,	,	PUNCT
eurjchem-1645	484	21	9h	9h	NUM
eurjchem-1645	484	22	,	,	PUNCT
eurjchem-1645	484	23	t‐bu	t‐bu	NOUN
eurjchem-1645	484	24	)	)	PUNCT
eurjchem-1645	484	25	,	,	PUNCT
eurjchem-1645	484	26	2.8	2.8	NUM
eurjchem-1645	484	27	(	(	PUNCT
eurjchem-1645	484	28	q	q	NOUN
eurjchem-1645	484	29	,	,	PUNCT
eurjchem-1645	484	30	2h	2h	NUM
eurjchem-1645	484	31	,	,	PUNCT
eurjchem-1645	484	32	ch2	ch2	PROPN
eurjchem-1645	484	33	)	)	PUNCT
eurjchem-1645	484	34	,	,	PUNCT
eurjchem-1645	484	35	4.2	4.2	NUM
eurjchem-1645	484	36	(	(	PUNCT
eurjchem-1645	484	37	q	q	NOUN
eurjchem-1645	484	38	,	,	PUNCT
eurjchem-1645	484	39	2h	2h	NUM
eurjchem-1645	484	40	,	,	PUNCT
eurjchem-1645	484	41	n‐ch2	n‐ch2	PROPN
eurjchem-1645	484	42	)	)	PUNCT
eurjchem-1645	484	43	,	,	PUNCT
eurjchem-1645	484	44	7.26	7.26	NUM
eurjchem-1645	484	45	(	(	PUNCT
eurjchem-1645	484	46	t	t	PROPN
eurjchem-1645	484	47	,	,	PUNCT
eurjchem-1645	484	48	1h	1h	NUM
eurjchem-1645	484	49	,	,	PUNCT
eurjchem-1645	484	50	j	j	PROPN
eurjchem-1645	484	51	=	=	SYM
eurjchem-1645	484	52	7.2	7.2	NUM
eurjchem-1645	484	53	hz	hz	NOUN
eurjchem-1645	484	54	,	,	PUNCT
eurjchem-1645	484	55	ar‐h	ar‐h	NOUN
eurjchem-1645	484	56	)	)	PUNCT
eurjchem-1645	484	57	,	,	PUNCT
eurjchem-1645	484	58	7.42	7.42	NUM
eurjchem-1645	484	59	(	(	PUNCT
eurjchem-1645	484	60	d	d	PROPN
eurjchem-1645	484	61	,	,	PUNCT
eurjchem-1645	484	62	1h	1h	NUM
eurjchem-1645	484	63	,	,	PUNCT
eurjchem-1645	484	64	j	j	PROPN
eurjchem-1645	484	65	=	=	SYM
eurjchem-1645	484	66	7.4	7.4	NUM
eurjchem-1645	484	67	hz	hz	VERB
eurjchem-1645	484	68	,	,	PUNCT
eurjchem-1645	484	69	ar‐h	ar‐h	NOUN
eurjchem-1645	484	70	)	)	PUNCT
eurjchem-1645	484	71	,	,	PUNCT
eurjchem-1645	484	72	7.64	7.64	NUM
eurjchem-1645	484	73	(	(	PUNCT
eurjchem-1645	484	74	d	d	PROPN
eurjchem-1645	484	75	,	,	PUNCT
eurjchem-1645	484	76	1h	1h	NUM
eurjchem-1645	484	77	,	,	PUNCT
eurjchem-1645	484	78	j	j	PROPN
eurjchem-1645	484	79	=	=	SYM
eurjchem-1645	484	80	8	8	NUM
eurjchem-1645	484	81	hz	hz	NOUN
eurjchem-1645	484	82	,	,	PUNCT
eurjchem-1645	484	83	ar‐h	ar‐h	NOUN
eurjchem-1645	484	84	)	)	PUNCT
eurjchem-1645	484	85	,	,	PUNCT
eurjchem-1645	484	86	7.82	7.82	NUM
eurjchem-1645	484	87	(	(	PUNCT
eurjchem-1645	484	88	t	t	PROPN
eurjchem-1645	484	89	,	,	PUNCT
eurjchem-1645	484	90	1h	1h	NUM
eurjchem-1645	484	91	,	,	PUNCT
eurjchem-1645	484	92	j	j	PROPN
eurjchem-1645	484	93	=	=	SYM
eurjchem-1645	484	94	7.6	7.6	NUM
eurjchem-1645	484	95	hz	hz	NOUN
eurjchem-1645	484	96	,	,	PUNCT
eurjchem-1645	484	97	ar‐h	ar‐h	PROPN
eurjchem-1645	484	98	)	)	PUNCT
eurjchem-1645	484	99	,	,	PUNCT
eurjchem-1645	484	100	8.12	8.12	NUM
eurjchem-1645	484	101	(	(	PUNCT
eurjchem-1645	484	102	d	d	PROPN
eurjchem-1645	484	103	,	,	PUNCT
eurjchem-1645	484	104	2h	2h	NUM
eurjchem-1645	484	105	,	,	PUNCT
eurjchem-1645	484	106	j	j	PROPN
eurjchem-1645	484	107	=	=	SYM
eurjchem-1645	484	108	7.4	7.4	NUM
eurjchem-1645	484	109	hz	hz	VERB
eurjchem-1645	484	110	,	,	PUNCT
eurjchem-1645	484	111	ar‐h	ar‐h	PROPN
eurjchem-1645	484	112	)	)	PUNCT
eurjchem-1645	484	113	,	,	PUNCT
eurjchem-1645	484	114	8.8	8.8	NUM
eurjchem-1645	484	115	(	(	PUNCT
eurjchem-1645	484	116	d	d	PROPN
eurjchem-1645	484	117	,	,	PUNCT
eurjchem-1645	484	118	2h	2h	NUM
eurjchem-1645	484	119	,	,	PUNCT
eurjchem-1645	484	120	j	j	PROPN
eurjchem-1645	484	121	=	=	SYM
eurjchem-1645	484	122	7.6	7.6	NUM
eurjchem-1645	484	123	hz	hz	NOUN
eurjchem-1645	484	124	,	,	PUNCT
eurjchem-1645	484	125	ar‐h	ar‐h	PROPN
eurjchem-1645	484	126	)	)	PUNCT
eurjchem-1645	484	127	,	,	PUNCT
eurjchem-1645	484	128	8.96	8.96	NUM
eurjchem-1645	484	129	(	(	PUNCT
eurjchem-1645	484	130	s	s	PROPN
eurjchem-1645	484	131	,	,	PUNCT
eurjchem-1645	484	132	1h	1h	NUM
eurjchem-1645	484	133	,	,	PUNCT
eurjchem-1645	484	134	ar‐h	ar‐h	NOUN
eurjchem-1645	484	135	)	)	PUNCT
eurjchem-1645	484	136	.	.	PUNCT
eurjchem-1645	485	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	485	2	(	(	PUNCT
eurjchem-1645	485	3	ei	ei	X
eurjchem-1645	485	4	,	,	PUNCT
eurjchem-1645	485	5	m	m	PROPN
eurjchem-1645	485	6	/	/	SYM
eurjchem-1645	485	7	z	z	NOUN
eurjchem-1645	485	8	):	):	PUNCT
eurjchem-1645	485	9	443	443	NUM
eurjchem-1645	485	10	(	(	PUNCT
eurjchem-1645	485	11	m+h	m+h	NOUN
eurjchem-1645	485	12	)	)	PUNCT
eurjchem-1645	485	13	.	.	PUNCT
eurjchem-1645	486	1	anal	anal	PROPN
eurjchem-1645	486	2	.	.	PUNCT
eurjchem-1645	486	3	calcd	calcd	NOUN
eurjchem-1645	486	4	.	.	PUNCT
eurjchem-1645	487	1	for	for	SCONJ
eurjchem-1645	487	2	c24h22n6o3	c24h22n6o3	PROPN
eurjchem-1645	487	3	:	:	PUNCT
eurjchem-1645	487	4	c	c	X
eurjchem-1645	487	5	,	,	PUNCT
eurjchem-1645	487	6	65.15	65.15	NUM
eurjchem-1645	487	7	;	;	PUNCT
eurjchem-1645	487	8	h	h	NOUN
eurjchem-1645	487	9	,	,	PUNCT
eurjchem-1645	487	10	5.01	5.01	NUM
eurjchem-1645	487	11	;	;	PUNCT
eurjchem-1645	487	12	n	n	CCONJ
eurjchem-1645	487	13	,	,	PUNCT
eurjchem-1645	487	14	18.99	18.99	NUM
eurjchem-1645	487	15	.	.	PUNCT
eurjchem-1645	487	16	found	find	VERB
eurjchem-1645	487	17	:	:	PUNCT
eurjchem-1645	488	1	c	c	X
eurjchem-1645	488	2	,	,	PUNCT
eurjchem-1645	488	3	65.13	65.13	NUM
eurjchem-1645	488	4	;	;	PUNCT
eurjchem-1645	488	5	h	h	NOUN
eurjchem-1645	488	6	,	,	PUNCT
eurjchem-1645	488	7	5.02	5.02	NUM
eurjchem-1645	488	8	;	;	PUNCT
eurjchem-1645	488	9	n	n	CCONJ
eurjchem-1645	488	10	,	,	PUNCT
eurjchem-1645	488	11	18.97	18.97	NUM
eurjchem-1645	488	12	%	%	NOUN
eurjchem-1645	488	13	.	.	PUNCT
eurjchem-1645	489	1	2.2.14	2.2.14	X
eurjchem-1645	489	2	.	.	PUNCT
eurjchem-1645	489	3	general	general	ADJ
eurjchem-1645	489	4	procedure	procedure	NOUN
eurjchem-1645	489	5	for	for	ADP
eurjchem-1645	489	6	synthesis	synthesis	NOUN
eurjchem-1645	489	7	of	of	ADP
eurjchem-1645	489	8	compounds	compound	NOUN
eurjchem-1645	489	9	15a‐	15a‐	PROPN
eurjchem-1645	489	10	h	h	NOUN
eurjchem-1645	489	11	,	,	PUNCT
eurjchem-1645	489	12	step	step	NOUN
eurjchem-1645	489	13	(	(	PUNCT
eurjchem-1645	489	14	b	b	NOUN
eurjchem-1645	489	15	)	)	PUNCT
eurjchem-1645	489	16	to	to	ADP
eurjchem-1645	489	17	a	a	DET
eurjchem-1645	489	18	stirred	stir	VERB
eurjchem-1645	489	19	solution	solution	NOUN
eurjchem-1645	489	20	of	of	ADP
eurjchem-1645	489	21	compounds	compound	NOUN
eurjchem-1645	489	22	14a‐h	14a‐h	NOUN
eurjchem-1645	489	23	(	(	PUNCT
eurjchem-1645	489	24	1	1	NUM
eurjchem-1645	489	25	mmol	mmol	NOUN
eurjchem-1645	489	26	)	)	PUNCT
eurjchem-1645	489	27	was	be	AUX
eurjchem-1645	489	28	dissolved	dissolve	VERB
eurjchem-1645	489	29	in	in	ADP
eurjchem-1645	489	30	2	2	NUM
eurjchem-1645	489	31	n	n	PRON
eurjchem-1645	489	32	dioxane	dioxane	NOUN
eurjchem-1645	489	33	in	in	ADP
eurjchem-1645	489	34	hcl	hcl	PROPN
eurjchem-1645	489	35	(	(	PUNCT
eurjchem-1645	489	36	10	10	NUM
eurjchem-1645	489	37	ml	ml	NOUN
eurjchem-1645	489	38	)	)	PUNCT
eurjchem-1645	489	39	and	and	CCONJ
eurjchem-1645	489	40	stirred	stir	VERB
eurjchem-1645	489	41	reaction	reaction	NOUN
eurjchem-1645	489	42	mixture	mixture	NOUN
eurjchem-1645	489	43	to	to	PART
eurjchem-1645	489	44	room	room	VERB
eurjchem-1645	489	45	temperature	temperature	NOUN
eurjchem-1645	489	46	for	for	ADP
eurjchem-1645	489	47	6	6	NUM
eurjchem-1645	489	48	h.	h.	NOUN
eurjchem-1645	489	49	progress	progress	NOUN
eurjchem-1645	489	50	of	of	ADP
eurjchem-1645	489	51	reaction	reaction	NOUN
eurjchem-1645	489	52	was	be	AUX
eurjchem-1645	489	53	monitored	monitor	VERB
eurjchem-1645	489	54	by	by	ADP
eurjchem-1645	489	55	lc‐ms	lc‐ms	PRON
eurjchem-1645	489	56	for	for	ADP
eurjchem-1645	489	57	the	the	DET
eurjchem-1645	489	58	consumption	consumption	NOUN
eurjchem-1645	489	59	of	of	ADP
eurjchem-1645	489	60	starting	start	VERB
eurjchem-1645	489	61	material	material	NOUN
eurjchem-1645	489	62	.	.	PUNCT
eurjchem-1645	490	1	after	after	ADP
eurjchem-1645	490	2	completion	completion	NOUN
eurjchem-1645	490	3	the	the	DET
eurjchem-1645	490	4	reaction	reaction	NOUN
eurjchem-1645	490	5	,	,	PUNCT
eurjchem-1645	490	6	the	the	DET
eurjchem-1645	490	7	reaction	reaction	NOUN
eurjchem-1645	490	8	mixture	mixture	NOUN
eurjchem-1645	490	9	evaporated	evaporate	VERB
eurjchem-1645	490	10	under	under	ADP
eurjchem-1645	490	11	reduced	reduced	ADJ
eurjchem-1645	490	12	pressure	pressure	NOUN
eurjchem-1645	490	13	to	to	PART
eurjchem-1645	490	14	obtain	obtain	VERB
eurjchem-1645	490	15	yellow	yellow	ADJ
eurjchem-1645	490	16	gummy	gummy	ADJ
eurjchem-1645	490	17	material	material	NOUN
eurjchem-1645	490	18	.	.	PUNCT
eurjchem-1645	491	1	the	the	DET
eurjchem-1645	491	2	obtained	obtain	VERB
eurjchem-1645	491	3	crude	crude	NOUN
eurjchem-1645	491	4	was	be	AUX
eurjchem-1645	491	5	washed	wash	VERB
eurjchem-1645	491	6	with	with	ADP
eurjchem-1645	491	7	10	10	NUM
eurjchem-1645	491	8	%	%	NOUN
eurjchem-1645	491	9	ethyl	ethyl	PROPN
eurjchem-1645	491	10	acetate	acetate	NOUN
eurjchem-1645	491	11	:	:	PUNCT
eurjchem-1645	491	12	hexane	hexane	NOUN
eurjchem-1645	491	13	,	,	PUNCT
eurjchem-1645	491	14	hexane	hexane	NOUN
eurjchem-1645	491	15	and	and	CCONJ
eurjchem-1645	491	16	diethyl	diethyl	NOUN
eurjchem-1645	491	17	ether	ether	NOUN
eurjchem-1645	491	18	to	to	PART
eurjchem-1645	491	19	obtain	obtain	VERB
eurjchem-1645	491	20	crude	crude	ADJ
eurjchem-1645	491	21	15a‐h	15a‐h	NOUN
eurjchem-1645	491	22	as	as	ADP
eurjchem-1645	491	23	yellow	yellow	ADJ
eurjchem-1645	491	24	solid	solid	ADJ
eurjchem-1645	491	25	material	material	NOUN
eurjchem-1645	491	26	.	.	PUNCT
eurjchem-1645	492	1	the	the	DET
eurjchem-1645	492	2	obtained	obtain	VERB
eurjchem-1645	492	3	compound	compound	NOUN
eurjchem-1645	492	4	was	be	AUX
eurjchem-1645	492	5	purified	purify	VERB
eurjchem-1645	492	6	by	by	ADP
eurjchem-1645	492	7	column	column	NOUN
eurjchem-1645	492	8	chromatography	chromatography	NOUN
eurjchem-1645	492	9	by	by	ADP
eurjchem-1645	492	10	using	use	VERB
eurjchem-1645	492	11	silica	silica	NOUN
eurjchem-1645	492	12	gel	gel	NOUN
eurjchem-1645	492	13	(	(	PUNCT
eurjchem-1645	492	14	230‐400	230‐400	PROPN
eurjchem-1645	492	15	mesh	mesh	NOUN
eurjchem-1645	492	16	)	)	PUNCT
eurjchem-1645	492	17	by	by	ADP
eurjchem-1645	492	18	using	use	VERB
eurjchem-1645	492	19	25‐75	25‐75	NUM
eurjchem-1645	492	20	%	%	NOUN
eurjchem-1645	492	21	ethyl	ethyl	PROPN
eurjchem-1645	492	22	acetate	acetate	NOUN
eurjchem-1645	492	23	and	and	CCONJ
eurjchem-1645	492	24	hexane	hexane	NOUN
eurjchem-1645	492	25	to	to	PART
eurjchem-1645	492	26	obtain	obtain	VERB
eurjchem-1645	492	27	desired	desire	VERB
eurjchem-1645	492	28	compound	compound	NOUN
eurjchem-1645	492	29	15a‐h	15a‐h	NOUN
eurjchem-1645	492	30	as	as	ADP
eurjchem-1645	492	31	solid	solid	ADJ
eurjchem-1645	492	32	materials	material	NOUN
eurjchem-1645	492	33	.	.	PUNCT
eurjchem-1645	493	1	3‐(benzofuran‐2‐yl)‐5,6‐dihydro‐6‐(3‐methoxyphenyl)‐1h‐	3‐(benzofuran‐2‐yl)‐5,6‐dihydro‐6‐(3‐methoxyphenyl)‐1h‐	NUM
eurjchem-1645	493	2	pyrazolo[3,4‐c]pyridin‐7(4h)‐one	pyrazolo[3,4‐c]pyridin‐7(4h)‐one	NOUN
eurjchem-1645	493	3	(	(	PUNCT
eurjchem-1645	493	4	15a	15a	NOUN
eurjchem-1645	493	5	):	):	PUNCT
eurjchem-1645	493	6	color	color	NOUN
eurjchem-1645	493	7	:	:	PUNCT
eurjchem-1645	493	8	white	white	ADJ
eurjchem-1645	493	9	.	.	PUNCT
eurjchem-1645	494	1	yield	yield	NOUN
eurjchem-1645	494	2	:	:	PUNCT
eurjchem-1645	494	3	87	87	NUM
eurjchem-1645	494	4	%	%	NOUN
eurjchem-1645	494	5	.	.	PUNCT
eurjchem-1645	495	1	m.p	m.p	PROPN
eurjchem-1645	495	2	.	.	PROPN
eurjchem-1645	495	3	:	:	PUNCT
eurjchem-1645	496	1	191‐192	191‐192	NUM
eurjchem-1645	496	2	°	°	ADP
eurjchem-1645	496	3	c	c	NOUN
eurjchem-1645	496	4	.	.	PUNCT
eurjchem-1645	497	1	1h	1h	NUM
eurjchem-1645	497	2	nmr	nmr	NOUN
eurjchem-1645	497	3	(	(	PUNCT
eurjchem-1645	497	4	400	400	NUM
eurjchem-1645	497	5	mhz	mhz	NOUN
eurjchem-1645	497	6	,	,	PUNCT
eurjchem-1645	497	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	497	8	,	,	PUNCT
eurjchem-1645	497	9	δ	δ	PROPN
eurjchem-1645	497	10	,	,	PUNCT
eurjchem-1645	497	11	ppm	ppm	NUM
eurjchem-1645	497	12	):	):	PUNCT
eurjchem-1645	497	13	3.21	3.21	NUM
eurjchem-1645	497	14	(	(	PUNCT
eurjchem-1645	497	15	t	t	PROPN
eurjchem-1645	497	16	,	,	PUNCT
eurjchem-1645	497	17	2h	2h	NUM
eurjchem-1645	497	18	,	,	PUNCT
eurjchem-1645	497	19	j	j	PROPN
eurjchem-1645	497	20	=	=	SYM
eurjchem-1645	497	21	7.6	7.6	NUM
eurjchem-1645	497	22	hz	hz	NOUN
eurjchem-1645	497	23	,	,	PUNCT
eurjchem-1645	497	24	ch2	ch2	PROPN
eurjchem-1645	497	25	)	)	PUNCT
eurjchem-1645	497	26	,	,	PUNCT
eurjchem-1645	497	27	3.31	3.31	NUM
eurjchem-1645	497	28	(	(	PUNCT
eurjchem-1645	497	29	s	s	PROPN
eurjchem-1645	497	30	,	,	PUNCT
eurjchem-1645	497	31	3h	3h	NUM
eurjchem-1645	497	32	,	,	PUNCT
eurjchem-1645	497	33	o‐ch3	o‐ch3	PROPN
eurjchem-1645	497	34	)	)	PUNCT
eurjchem-1645	497	35	,	,	PUNCT
eurjchem-1645	497	36	4.18	4.18	NUM
eurjchem-1645	497	37	(	(	PUNCT
eurjchem-1645	497	38	d	d	NOUN
eurjchem-1645	497	39	,	,	PUNCT
eurjchem-1645	497	40	2h	2h	NUM
eurjchem-1645	497	41	,	,	PUNCT
eurjchem-1645	497	42	j	j	PROPN
eurjchem-1645	497	43	=	=	SYM
eurjchem-1645	497	44	7.6	7.6	NUM
eurjchem-1645	497	45	hz	hz	NOUN
eurjchem-1645	497	46	,	,	PUNCT
eurjchem-1645	497	47	n‐ch2	n‐ch2	PROPN
eurjchem-1645	497	48	)	)	PUNCT
eurjchem-1645	497	49	,	,	PUNCT
eurjchem-1645	497	50	6.82	6.82	NUM
eurjchem-1645	497	51	(	(	PUNCT
eurjchem-1645	497	52	d	d	PROPN
eurjchem-1645	497	53	,	,	PUNCT
eurjchem-1645	497	54	1h	1h	NUM
eurjchem-1645	497	55	,	,	PUNCT
eurjchem-1645	497	56	j	j	PROPN
eurjchem-1645	497	57	=	=	SYM
eurjchem-1645	497	58	7.6	7.6	NUM
eurjchem-1645	497	59	hz	hz	NOUN
eurjchem-1645	497	60	,	,	PUNCT
eurjchem-1645	497	61	ar‐h	ar‐h	NOUN
eurjchem-1645	497	62	)	)	PUNCT
eurjchem-1645	497	63	,	,	PUNCT
eurjchem-1645	497	64	6.89‐6.79	6.89‐6.79	NUM
eurjchem-1645	497	65	(	(	PUNCT
eurjchem-1645	497	66	m	m	PROPN
eurjchem-1645	497	67	,	,	PUNCT
eurjchem-1645	497	68	2h	2h	NUM
eurjchem-1645	497	69	,	,	PUNCT
eurjchem-1645	497	70	ar‐h	ar‐h	NOUN
eurjchem-1645	497	71	)	)	PUNCT
eurjchem-1645	497	72	,	,	PUNCT
eurjchem-1645	497	73	7.40‐7.21	7.40‐7.21	PROPN
eurjchem-1645	497	74	(	(	PUNCT
eurjchem-1645	497	75	m	m	PROPN
eurjchem-1645	497	76	4h	4h	NUM
eurjchem-1645	497	77	,	,	PUNCT
eurjchem-1645	497	78	ar‐h	ar‐h	NOUN
eurjchem-1645	497	79	)	)	PUNCT
eurjchem-1645	497	80	,	,	PUNCT
eurjchem-1645	497	81	7.76‐7.60	7.76‐7.60	NUM
eurjchem-1645	497	82	(	(	PUNCT
eurjchem-1645	497	83	m	m	PROPN
eurjchem-1645	497	84	,	,	PUNCT
eurjchem-1645	497	85	2h	2h	NUM
eurjchem-1645	497	86	,	,	PUNCT
eurjchem-1645	497	87	ar‐h	ar‐h	NOUN
eurjchem-1645	497	88	)	)	PUNCT
eurjchem-1645	497	89	,	,	PUNCT
eurjchem-1645	497	90	14.4	14.4	NUM
eurjchem-1645	497	91	(	(	PUNCT
eurjchem-1645	497	92	br	br	PROPN
eurjchem-1645	497	93	,	,	PUNCT
eurjchem-1645	497	94	1h	1h	NUM
eurjchem-1645	497	95	,	,	PUNCT
eurjchem-1645	497	96	nh	nh	PROPN
eurjchem-1645	497	97	)	)	PUNCT
eurjchem-1645	497	98	.	.	PUNCT
eurjchem-1645	498	1	13c	13c	NOUN
eurjchem-1645	498	2	nmr	nmr	NOUN
eurjchem-1645	498	3	(	(	PUNCT
eurjchem-1645	498	4	100	100	NUM
eurjchem-1645	498	5	mhz	mhz	NOUN
eurjchem-1645	498	6	,	,	PUNCT
eurjchem-1645	498	7	cdcl3	cdcl3	PROPN
eurjchem-1645	498	8	,	,	PUNCT
eurjchem-1645	498	9	δ	δ	PROPN
eurjchem-1645	498	10	,	,	PUNCT
eurjchem-1645	498	11	ppm	ppm	NOUN
eurjchem-1645	498	12	):	):	PUNCT
eurjchem-1645	498	13	10.64	10.64	NUM
eurjchem-1645	498	14	,	,	PUNCT
eurjchem-1645	498	15	51.82	51.82	NUM
eurjchem-1645	498	16	,	,	PUNCT
eurjchem-1645	498	17	55.85	55.85	NUM
eurjchem-1645	498	18	,	,	PUNCT
eurjchem-1645	498	19	97.46	97.46	NUM
eurjchem-1645	498	20	,	,	PUNCT
eurjchem-1645	498	21	103.31	103.31	NUM
eurjchem-1645	498	22	,	,	PUNCT
eurjchem-1645	498	23	103.61	103.61	NUM
eurjchem-1645	498	24	,	,	PUNCT
eurjchem-1645	498	25	106.61	106.61	NUM
eurjchem-1645	498	26	,	,	PUNCT
eurjchem-1645	498	27	111.02	111.02	NUM
eurjchem-1645	498	28	,	,	PUNCT
eurjchem-1645	498	29	121.18	121.18	NUM
eurjchem-1645	498	30	,	,	PUNCT
eurjchem-1645	498	31	122.34	122.34	NUM
eurjchem-1645	498	32	,	,	PUNCT
eurjchem-1645	498	33	123.76	123.76	NUM
eurjchem-1645	498	34	,	,	PUNCT
eurjchem-1645	498	35	124.44	124.44	NUM
eurjchem-1645	498	36	,	,	PUNCT
eurjchem-1645	498	37	128.84	128.84	NUM
eurjchem-1645	498	38	,	,	PUNCT
eurjchem-1645	498	39	134.67	134.67	NUM
eurjchem-1645	498	40	,	,	PUNCT
eurjchem-1645	498	41	150.42	150.42	NUM
eurjchem-1645	498	42	,	,	PUNCT
eurjchem-1645	498	43	150.67	150.67	NUM
eurjchem-1645	498	44	,	,	PUNCT
eurjchem-1645	498	45	156.61	156.61	NUM
eurjchem-1645	498	46	,	,	PUNCT
eurjchem-1645	498	47	156.88	156.88	NUM
eurjchem-1645	498	48	,	,	PUNCT
eurjchem-1645	498	49	161.72	161.72	NUM
eurjchem-1645	498	50	.	.	PUNCT
eurjchem-1645	499	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	499	2	(	(	PUNCT
eurjchem-1645	499	3	ei	ei	PROPN
eurjchem-1645	499	4	,	,	PUNCT
eurjchem-1645	499	5	m	m	PROPN
eurjchem-1645	499	6	/	/	SYM
eurjchem-1645	499	7	z	z	NOUN
eurjchem-1645	499	8	):	):	PUNCT
eurjchem-1645	499	9	360	360	NUM
eurjchem-1645	499	10	(	(	PUNCT
eurjchem-1645	499	11	m+h	m+h	NOUN
eurjchem-1645	499	12	)	)	PUNCT
eurjchem-1645	499	13	.	.	PUNCT
eurjchem-1645	500	1	anal	anal	PROPN
eurjchem-1645	500	2	.	.	PUNCT
eurjchem-1645	500	3	calcd	calcd	NOUN
eurjchem-1645	500	4	.	.	PUNCT
eurjchem-1645	501	1	for	for	ADP
eurjchem-1645	501	2	c21h17n3o3	c21h17n3o3	NOUN
eurjchem-1645	501	3	:	:	PUNCT
eurjchem-1645	501	4	c	c	X
eurjchem-1645	501	5	,	,	PUNCT
eurjchem-1645	501	6	70.18	70.18	NUM
eurjchem-1645	501	7	;	;	PUNCT
eurjchem-1645	501	8	h	h	NOUN
eurjchem-1645	501	9	,	,	PUNCT
eurjchem-1645	501	10	4.77	4.77	NUM
eurjchem-1645	501	11	;	;	PUNCT
eurjchem-1645	501	12	n	n	CCONJ
eurjchem-1645	501	13	,	,	PUNCT
eurjchem-1645	501	14	11.69	11.69	NUM
eurjchem-1645	501	15	.	.	PUNCT
eurjchem-1645	501	16	found	find	VERB
eurjchem-1645	501	17	:	:	PUNCT
eurjchem-1645	502	1	c	c	X
eurjchem-1645	502	2	,	,	PUNCT
eurjchem-1645	502	3	70.16	70.16	NUM
eurjchem-1645	502	4	;	;	PUNCT
eurjchem-1645	503	1	h	h	NOUN
eurjchem-1645	503	2	,	,	PUNCT
eurjchem-1645	503	3	4.74	4.74	NUM
eurjchem-1645	503	4	;	;	PUNCT
eurjchem-1645	503	5	n	n	CCONJ
eurjchem-1645	503	6	,	,	PUNCT
eurjchem-1645	503	7	11.70	11.70	NUM
eurjchem-1645	503	8	%	%	NOUN
eurjchem-1645	503	9	.	.	PUNCT
eurjchem-1645	504	1	hplc	hplc	NOUN
eurjchem-1645	504	2	:	:	PUNCT
eurjchem-1645	504	3	r.t	r.t	PROPN
eurjchem-1645	504	4	.	.	PUNCT
eurjchem-1645	504	5	=	=	NOUN
eurjchem-1645	504	6	6.18	6.18	NUM
eurjchem-1645	504	7	min	min	NOUN
eurjchem-1645	504	8	,	,	PUNCT
eurjchem-1645	504	9	purity	purity	NOUN
eurjchem-1645	504	10	=	=	SYM
eurjchem-1645	504	11	99.3	99.3	NUM
eurjchem-1645	504	12	%	%	NOUN
eurjchem-1645	504	13	.	.	PUNCT
eurjchem-1645	505	1	3‐(benzo[b]thiophen‐2‐yl)‐5	3‐(benzo[b]thiophen‐2‐yl)‐5	NUM
eurjchem-1645	505	2	,	,	PUNCT
eurjchem-1645	505	3	6‐dihydro‐6‐(3‐methoxyphen	6‐dihydro‐6‐(3‐methoxyphen	PROPN
eurjchem-1645	505	4	yl)‐1h‐pyrazolo[3,4‐c]pyridin‐7(4h)‐one	yl)‐1h‐pyrazolo[3,4‐c]pyridin‐7(4h)‐one	PROPN
eurjchem-1645	505	5	(	(	PUNCT
eurjchem-1645	505	6	15b	15b	NUM
eurjchem-1645	505	7	):	):	PUNCT
eurjchem-1645	505	8	color	color	NOUN
eurjchem-1645	505	9	:	:	PUNCT
eurjchem-1645	505	10	yellow	yellow	ADJ
eurjchem-1645	505	11	.	.	PUNCT
eurjchem-1645	506	1	yield	yield	NOUN
eurjchem-1645	506	2	:	:	PUNCT
eurjchem-1645	506	3	88	88	NUM
eurjchem-1645	506	4	%	%	NOUN
eurjchem-1645	506	5	.	.	PUNCT
eurjchem-1645	507	1	m.p	m.p	PROPN
eurjchem-1645	507	2	.	.	PROPN
eurjchem-1645	507	3	:	:	PUNCT
eurjchem-1645	507	4	188‐189	188‐189	NUM
eurjchem-1645	507	5	°	°	PROPN
eurjchem-1645	507	6	c	c	PROPN
eurjchem-1645	507	7	.	.	PUNCT
eurjchem-1645	508	1	1h	1h	NUM
eurjchem-1645	508	2	nmr	nmr	NOUN
eurjchem-1645	508	3	(	(	PUNCT
eurjchem-1645	508	4	400	400	NUM
eurjchem-1645	508	5	mhz	mhz	NOUN
eurjchem-1645	508	6	,	,	PUNCT
eurjchem-1645	508	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	508	8	,	,	PUNCT
eurjchem-1645	508	9	δ	δ	PROPN
eurjchem-1645	508	10	,	,	PUNCT
eurjchem-1645	508	11	ppm	ppm	NUM
eurjchem-1645	508	12	):	):	PUNCT
eurjchem-1645	508	13	3.40	3.40	NUM
eurjchem-1645	508	14	(	(	PUNCT
eurjchem-1645	508	15	t	t	PROPN
eurjchem-1645	508	16	,	,	PUNCT
eurjchem-1645	508	17	2h	2h	NUM
eurjchem-1645	508	18	,	,	PUNCT
eurjchem-1645	508	19	j	j	PROPN
eurjchem-1645	508	20	=	=	PROPN
eurjchem-1645	508	21	8.4	8.4	NUM
eurjchem-1645	508	22	hz	hz	NOUN
eurjchem-1645	508	23	,	,	PUNCT
eurjchem-1645	508	24	ch2	ch2	PROPN
eurjchem-1645	508	25	)	)	PUNCT
eurjchem-1645	508	26	,	,	PUNCT
eurjchem-1645	508	27	3.74	3.74	NUM
eurjchem-1645	508	28	(	(	PUNCT
eurjchem-1645	508	29	s	s	PROPN
eurjchem-1645	508	30	,	,	PUNCT
eurjchem-1645	508	31	3h	3h	NUM
eurjchem-1645	508	32	,	,	PUNCT
eurjchem-1645	508	33	o‐ch3	o‐ch3	PROPN
eurjchem-1645	508	34	)	)	PUNCT
eurjchem-1645	508	35	,	,	PUNCT
eurjchem-1645	508	36	4.24	4.24	NUM
eurjchem-1645	508	37	(	(	PUNCT
eurjchem-1645	508	38	d	d	PROPN
eurjchem-1645	508	39	,	,	PUNCT
eurjchem-1645	508	40	2h	2h	NUM
eurjchem-1645	508	41	,	,	PUNCT
eurjchem-1645	508	42	j	j	PROPN
eurjchem-1645	509	1	=	=	SYM
eurjchem-1645	509	2	6.2	6.2	NUM
eurjchem-1645	509	3	hz	hz	NOUN
eurjchem-1645	509	4	,	,	PUNCT
eurjchem-1645	509	5	n‐ch2	n‐ch2	PROPN
eurjchem-1645	509	6	)	)	PUNCT
eurjchem-1645	509	7	,	,	PUNCT
eurjchem-1645	509	8	6.38	6.38	NUM
eurjchem-1645	509	9	(	(	PUNCT
eurjchem-1645	509	10	d	d	PROPN
eurjchem-1645	509	11	,	,	PUNCT
eurjchem-1645	509	12	1h	1h	NUM
eurjchem-1645	509	13	,	,	PUNCT
eurjchem-1645	509	14	j	j	PROPN
eurjchem-1645	509	15	=	=	SYM
eurjchem-1645	509	16	7.6	7.6	NUM
eurjchem-1645	509	17	hz	hz	NOUN
eurjchem-1645	509	18	,	,	PUNCT
eurjchem-1645	509	19	ar‐h	ar‐h	PROPN
eurjchem-1645	509	20	)	)	PUNCT
eurjchem-1645	509	21	,	,	PUNCT
eurjchem-1645	509	22	6.50	6.50	NUM
eurjchem-1645	509	23	(	(	PUNCT
eurjchem-1645	509	24	s	s	PROPN
eurjchem-1645	509	25	,	,	PUNCT
eurjchem-1645	509	26	1h	1h	NUM
eurjchem-1645	509	27	,	,	PUNCT
eurjchem-1645	509	28	ar‐h	ar‐h	NOUN
eurjchem-1645	509	29	)	)	PUNCT
eurjchem-1645	509	30	,	,	PUNCT
eurjchem-1645	509	31	6.63‐6.57	6.63‐6.57	NUM
eurjchem-1645	509	32	(	(	PUNCT
eurjchem-1645	509	33	m	m	PROPN
eurjchem-1645	509	34	,	,	PUNCT
eurjchem-1645	509	35	2h	2h	NUM
eurjchem-1645	509	36	,	,	PUNCT
eurjchem-1645	509	37	ar‐h	ar‐h	NOUN
eurjchem-1645	509	38	)	)	PUNCT
eurjchem-1645	509	39	,	,	PUNCT
eurjchem-1645	509	40	7.21‐7.11	7.21‐7.11	NUM
eurjchem-1645	509	41	(	(	PUNCT
eurjchem-1645	509	42	m	m	PROPN
eurjchem-1645	509	43	,	,	PUNCT
eurjchem-1645	509	44	3h	3h	NUM
eurjchem-1645	509	45	,	,	PUNCT
eurjchem-1645	509	46	ar‐h	ar‐h	NOUN
eurjchem-1645	509	47	)	)	PUNCT
eurjchem-1645	509	48	,	,	PUNCT
eurjchem-1645	509	49	7.56‐	7.56‐	NUM
eurjchem-1645	509	50	7.44	7.44	NUM
eurjchem-1645	509	51	(	(	PUNCT
eurjchem-1645	509	52	dd	dd	NOUN
eurjchem-1645	509	53	,	,	PUNCT
eurjchem-1645	509	54	2h	2h	NUM
eurjchem-1645	509	55	,	,	PUNCT
eurjchem-1645	509	56	j	j	PROPN
eurjchem-1645	509	57	=	=	PROPN
eurjchem-1645	509	58	8.2	8.2	NUM
eurjchem-1645	509	59	hz	hz	NOUN
eurjchem-1645	509	60	,	,	PUNCT
eurjchem-1645	509	61	4.1hz	4.1hz	PROPN
eurjchem-1645	509	62	,	,	PUNCT
eurjchem-1645	509	63	ar‐h	ar‐h	PROPN
eurjchem-1645	509	64	)	)	PUNCT
eurjchem-1645	509	65	14.4	14.4	NUM
eurjchem-1645	509	66	(	(	PUNCT
eurjchem-1645	509	67	br	br	PROPN
eurjchem-1645	509	68	,	,	PUNCT
eurjchem-1645	509	69	1h	1h	NUM
eurjchem-1645	509	70	,	,	PUNCT
eurjchem-1645	509	71	nh	nh	PROPN
eurjchem-1645	509	72	)	)	PUNCT
eurjchem-1645	509	73	.	.	PUNCT
eurjchem-1645	510	1	13c	13c	NOUN
eurjchem-1645	510	2	nmr	nmr	NOUN
eurjchem-1645	510	3	(	(	PUNCT
eurjchem-1645	510	4	100	100	NUM
eurjchem-1645	510	5	mhz	mhz	NOUN
eurjchem-1645	510	6	,	,	PUNCT
eurjchem-1645	510	7	cdcl3	cdcl3	PROPN
eurjchem-1645	510	8	,	,	PUNCT
eurjchem-1645	510	9	δ	δ	PROPN
eurjchem-1645	510	10	,	,	PUNCT
eurjchem-1645	510	11	ppm	ppm	NOUN
eurjchem-1645	510	12	):	):	PUNCT
eurjchem-1645	510	13	13.54	13.54	NUM
eurjchem-1645	510	14	,	,	PUNCT
eurjchem-1645	510	15	52.82	52.82	NUM
eurjchem-1645	510	16	,	,	PUNCT
eurjchem-1645	510	17	55.65	55.65	NUM
eurjchem-1645	510	18	,	,	PUNCT
eurjchem-1645	510	19	98.46	98.46	NUM
eurjchem-1645	510	20	,	,	PUNCT
eurjchem-1645	510	21	104.31	104.31	NUM
eurjchem-1645	510	22	,	,	PUNCT
eurjchem-1645	510	23	104.61	104.61	NUM
eurjchem-1645	510	24	,	,	PUNCT
eurjchem-1645	510	25	108.66	108.66	NUM
eurjchem-1645	510	26	,	,	PUNCT
eurjchem-1645	510	27	111.12	111.12	NUM
eurjchem-1645	510	28	,	,	PUNCT
eurjchem-1645	510	29	121.18	121.18	NUM
eurjchem-1645	510	30	,	,	PUNCT
eurjchem-1645	510	31	122.34	122.34	NUM
eurjchem-1645	510	32	,	,	PUNCT
eurjchem-1645	510	33	123.76	123.76	NUM
eurjchem-1645	510	34	,	,	PUNCT
eurjchem-1645	510	35	124.44	124.44	NUM
eurjchem-1645	510	36	,	,	PUNCT
eurjchem-1645	510	37	128.84	128.84	NUM
eurjchem-1645	510	38	,	,	PUNCT
eurjchem-1645	510	39	134.67	134.67	NUM
eurjchem-1645	510	40	,	,	PUNCT
eurjchem-1645	510	41	150.42	150.42	NUM
eurjchem-1645	510	42	,	,	PUNCT
eurjchem-1645	510	43	150.67	150.67	NUM
eurjchem-1645	510	44	,	,	PUNCT
eurjchem-1645	510	45	156.8	156.8	NUM
eurjchem-1645	510	46	,	,	PUNCT
eurjchem-1645	510	47	157.00	157.00	NUM
eurjchem-1645	510	48	,	,	PUNCT
eurjchem-1645	510	49	161.73	161.73	NUM
eurjchem-1645	510	50	.	.	PUNCT
eurjchem-1645	511	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	511	2	(	(	PUNCT
eurjchem-1645	511	3	ei	ei	PROPN
eurjchem-1645	511	4	,	,	PUNCT
eurjchem-1645	511	5	m	m	PROPN
eurjchem-1645	511	6	/	/	SYM
eurjchem-1645	511	7	z	z	NOUN
eurjchem-1645	511	8	):	):	PUNCT
eurjchem-1645	511	9	375	375	NUM
eurjchem-1645	511	10	(	(	PUNCT
eurjchem-1645	511	11	m+h	m+h	PROPN
eurjchem-1645	511	12	)	)	PUNCT
eurjchem-1645	511	13	.	.	PUNCT
eurjchem-1645	512	1	anal	anal	PROPN
eurjchem-1645	512	2	.	.	PUNCT
eurjchem-1645	512	3	calcd	calcd	NOUN
eurjchem-1645	512	4	.	.	PUNCT
eurjchem-1645	513	1	for	for	ADP
eurjchem-1645	513	2	c21h17n3o2s	c21h17n3o2s	PROPN
eurjchem-1645	513	3	:	:	PUNCT
eurjchem-1645	513	4	c	c	X
eurjchem-1645	513	5	,	,	PUNCT
eurjchem-1645	513	6	67.18	67.18	NUM
eurjchem-1645	513	7	;	;	PUNCT
eurjchem-1645	513	8	h	h	X
eurjchem-1645	513	9	,	,	PUNCT
eurjchem-1645	513	10	4.56	4.56	NUM
eurjchem-1645	513	11	;	;	PUNCT
eurjchem-1645	513	12	n	n	CCONJ
eurjchem-1645	513	13	,	,	PUNCT
eurjchem-1645	513	14	11.19	11.19	NUM
eurjchem-1645	513	15	.	.	PUNCT
eurjchem-1645	513	16	found	find	VERB
eurjchem-1645	513	17	:	:	PUNCT
eurjchem-1645	514	1	c	c	X
eurjchem-1645	514	2	,	,	PUNCT
eurjchem-1645	514	3	67.16	67.16	NUM
eurjchem-1645	514	4	;	;	PUNCT
eurjchem-1645	514	5	h	h	NOUN
eurjchem-1645	514	6	,	,	PUNCT
eurjchem-1645	514	7	4.58	4.58	NUM
eurjchem-1645	514	8	;	;	PUNCT
eurjchem-1645	514	9	n	n	CCONJ
eurjchem-1645	514	10	,	,	PUNCT
eurjchem-1645	514	11	11.18	11.18	NUM
eurjchem-1645	514	12	%	%	NOUN
eurjchem-1645	514	13	.	.	PUNCT
eurjchem-1645	515	1	hplc	hplc	NOUN
eurjchem-1645	515	2	:	:	PUNCT
eurjchem-1645	515	3	r.t	r.t	PROPN
eurjchem-1645	515	4	.	.	PUNCT
eurjchem-1645	516	1	=	=	NOUN
eurjchem-1645	516	2	7.63	7.63	NUM
eurjchem-1645	516	3	min	min	NOUN
eurjchem-1645	516	4	,	,	PUNCT
eurjchem-1645	516	5	purity	purity	NOUN
eurjchem-1645	516	6	=	=	NOUN
eurjchem-1645	516	7	99.7	99.7	NUM
eurjchem-1645	516	8	%	%	NOUN
eurjchem-1645	516	9	.	.	PUNCT
eurjchem-1645	517	1	5,6‐dihydro‐6‐(3‐methoxyphenyl)‐3‐(quinolin‐3‐yl)‐1h‐pyra	5,6‐dihydro‐6‐(3‐methoxyphenyl)‐3‐(quinolin‐3‐yl)‐1h‐pyra	NUM
eurjchem-1645	517	2	zolo[3,4‐c]pyridin‐7(4h)‐one	zolo[3,4‐c]pyridin‐7(4h)‐one	NOUN
eurjchem-1645	517	3	(	(	PUNCT
eurjchem-1645	517	4	15c	15c	NOUN
eurjchem-1645	517	5	):	):	PUNCT
eurjchem-1645	517	6	color	color	NOUN
eurjchem-1645	517	7	:	:	PUNCT
eurjchem-1645	517	8	off	off	ADP
eurjchem-1645	517	9	white	white	PROPN
eurjchem-1645	517	10	.	.	PUNCT
eurjchem-1645	518	1	yield	yield	NOUN
eurjchem-1645	518	2	:	:	PUNCT
eurjchem-1645	518	3	91	91	NUM
eurjchem-1645	518	4	%	%	NOUN
eurjchem-1645	518	5	.	.	PUNCT
eurjchem-1645	519	1	m.p	m.p	PROPN
eurjchem-1645	519	2	.	.	PROPN
eurjchem-1645	519	3	:	:	PUNCT
eurjchem-1645	520	1	193‐194	193‐194	NUM
eurjchem-1645	520	2	°	°	PROPN
eurjchem-1645	520	3	c	c	PROPN
eurjchem-1645	520	4	.	.	PUNCT
eurjchem-1645	521	1	1h	1h	NUM
eurjchem-1645	521	2	nmr	nmr	NOUN
eurjchem-1645	521	3	(	(	PUNCT
eurjchem-1645	521	4	400	400	NUM
eurjchem-1645	521	5	mhz	mhz	NOUN
eurjchem-1645	521	6	,	,	PUNCT
eurjchem-1645	521	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	521	8	,	,	PUNCT
eurjchem-1645	521	9	δ	δ	PROPN
eurjchem-1645	521	10	,	,	PUNCT
eurjchem-1645	521	11	ppm	ppm	NUM
eurjchem-1645	521	12	):	):	PUNCT
eurjchem-1645	521	13	3.21	3.21	NUM
eurjchem-1645	521	14	(	(	PUNCT
eurjchem-1645	521	15	br	br	PROPN
eurjchem-1645	521	16	s	s	PROPN
eurjchem-1645	521	17	,	,	PUNCT
eurjchem-1645	521	18	2h	2h	NUM
eurjchem-1645	521	19	,	,	PUNCT
eurjchem-1645	521	20	ch2	ch2	PROPN
eurjchem-1645	521	21	)	)	PUNCT
eurjchem-1645	521	22	,	,	PUNCT
eurjchem-1645	521	23	3.83	3.83	NUM
eurjchem-1645	521	24	(	(	PUNCT
eurjchem-1645	521	25	s	s	PROPN
eurjchem-1645	521	26	,	,	PUNCT
eurjchem-1645	521	27	3h	3h	NUM
eurjchem-1645	521	28	,	,	PUNCT
eurjchem-1645	521	29	o‐ch3	o‐ch3	PROPN
eurjchem-1645	521	30	)	)	PUNCT
eurjchem-1645	521	31	,	,	PUNCT
eurjchem-1645	521	32	4.16	4.16	NUM
eurjchem-1645	521	33	(	(	PUNCT
eurjchem-1645	521	34	s	s	PROPN
eurjchem-1645	521	35	,	,	PUNCT
eurjchem-1645	521	36	2h	2h	NUM
eurjchem-1645	521	37	,	,	PUNCT
eurjchem-1645	521	38	n‐ch2	n‐ch2	PROPN
eurjchem-1645	521	39	)	)	PUNCT
eurjchem-1645	521	40	,	,	PUNCT
eurjchem-1645	521	41	6.93	6.93	NUM
eurjchem-1645	521	42	(	(	PUNCT
eurjchem-1645	521	43	d	d	PROPN
eurjchem-1645	521	44	,	,	PUNCT
eurjchem-1645	521	45	1h	1h	NUM
eurjchem-1645	521	46	,	,	PUNCT
eurjchem-1645	521	47	j	j	PROPN
eurjchem-1645	521	48	=	=	SYM
eurjchem-1645	521	49	7.8	7.8	NUM
eurjchem-1645	521	50	hz	hz	NOUN
eurjchem-1645	521	51	,	,	PUNCT
eurjchem-1645	521	52	ar‐h	ar‐h	NOUN
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eurjchem-1645	521	54	,	,	PUNCT
eurjchem-1645	521	55	7.12	7.12	NUM
eurjchem-1645	521	56	(	(	PUNCT
eurjchem-1645	521	57	d	d	PROPN
eurjchem-1645	521	58	,	,	PUNCT
eurjchem-1645	521	59	1h	1h	NUM
eurjchem-1645	521	60	,	,	PUNCT
eurjchem-1645	521	61	j	j	PROPN
eurjchem-1645	521	62	=	=	SYM
eurjchem-1645	521	63	8	8	NUM
eurjchem-1645	521	64	hz	hz	NOUN
eurjchem-1645	521	65	,	,	PUNCT
eurjchem-1645	521	66	ar‐h	ar‐h	NOUN
eurjchem-1645	521	67	)	)	PUNCT
eurjchem-1645	521	68	,	,	PUNCT
eurjchem-1645	521	69	7.18	7.18	NUM
eurjchem-1645	521	70	(	(	PUNCT
eurjchem-1645	521	71	s	s	PROPN
eurjchem-1645	521	72	,	,	PUNCT
eurjchem-1645	521	73	1h	1h	NUM
eurjchem-1645	521	74	,	,	PUNCT
eurjchem-1645	521	75	ar‐h	ar‐h	NOUN
eurjchem-1645	521	76	)	)	PUNCT
eurjchem-1645	521	77	,	,	PUNCT
eurjchem-1645	521	78	7.40	7.40	NUM
eurjchem-1645	521	79	(	(	PUNCT
eurjchem-1645	521	80	m	m	PROPN
eurjchem-1645	521	81	,	,	PUNCT
eurjchem-1645	521	82	1h	1h	NUM
eurjchem-1645	521	83	,	,	PUNCT
eurjchem-1645	521	84	ar‐h	ar‐h	NOUN
eurjchem-1645	521	85	)	)	PUNCT
eurjchem-1645	521	86	,	,	PUNCT
eurjchem-1645	521	87	7.58	7.58	NUM
eurjchem-1645	521	88	(	(	PUNCT
eurjchem-1645	521	89	t	t	PROPN
eurjchem-1645	521	90	,	,	PUNCT
eurjchem-1645	521	91	1h	1h	NUM
eurjchem-1645	521	92	,	,	PUNCT
eurjchem-1645	521	93	j	j	PROPN
eurjchem-1645	521	94	=	=	SYM
eurjchem-1645	521	95	7.2	7.2	NUM
eurjchem-1645	521	96	hz	hz	NOUN
eurjchem-1645	521	97	,	,	PUNCT
eurjchem-1645	521	98	ar‐h	ar‐h	NOUN
eurjchem-1645	521	99	)	)	PUNCT
eurjchem-1645	521	100	,	,	PUNCT
eurjchem-1645	521	101	7.73	7.73	NUM
eurjchem-1645	521	102	(	(	PUNCT
eurjchem-1645	521	103	t	t	PROPN
eurjchem-1645	521	104	,	,	PUNCT
eurjchem-1645	521	105	1h	1h	NUM
eurjchem-1645	521	106	,	,	PUNCT
eurjchem-1645	521	107	j	j	PROPN
eurjchem-1645	521	108	=	=	SYM
eurjchem-1645	521	109	7.2	7.2	NUM
eurjchem-1645	521	110	hz	hz	NOUN
eurjchem-1645	521	111	,	,	PUNCT
eurjchem-1645	521	112	ar‐h	ar‐h	NOUN
eurjchem-1645	521	113	)	)	PUNCT
eurjchem-1645	521	114	,	,	PUNCT
eurjchem-1645	521	115	7.84	7.84	NUM
eurjchem-1645	521	116	(	(	PUNCT
eurjchem-1645	521	117	d	d	PROPN
eurjchem-1645	521	118	,	,	PUNCT
eurjchem-1645	521	119	1h	1h	NUM
eurjchem-1645	521	120	,	,	PUNCT
eurjchem-1645	521	121	j	j	PROPN
eurjchem-1645	521	122	=	=	SYM
eurjchem-1645	521	123	7.6	7.6	NUM
eurjchem-1645	521	124	hz	hz	NOUN
eurjchem-1645	521	125	,	,	PUNCT
eurjchem-1645	521	126	ar‐h	ar‐h	PROPN
eurjchem-1645	521	127	)	)	PUNCT
eurjchem-1645	521	128	,	,	PUNCT
eurjchem-1645	521	129	8.15	8.15	NUM
eurjchem-1645	521	130	(	(	PUNCT
eurjchem-1645	521	131	d	d	PROPN
eurjchem-1645	521	132	,	,	PUNCT
eurjchem-1645	521	133	1h	1h	NUM
eurjchem-1645	521	134	,	,	PUNCT
eurjchem-1645	521	135	j	j	PROPN
eurjchem-1645	521	136	=	=	SYM
eurjchem-1645	521	137	7.6	7.6	NUM
eurjchem-1645	521	138	hz	hz	NOUN
eurjchem-1645	521	139	,	,	PUNCT
eurjchem-1645	521	140	ar‐h	ar‐h	PROPN
eurjchem-1645	521	141	)	)	PUNCT
eurjchem-1645	521	142	,	,	PUNCT
eurjchem-1645	521	143	8.56	8.56	NUM
eurjchem-1645	521	144	(	(	PUNCT
eurjchem-1645	521	145	s	s	PROPN
eurjchem-1645	521	146	,	,	PUNCT
eurjchem-1645	521	147	1h	1h	NUM
eurjchem-1645	521	148	,	,	PUNCT
eurjchem-1645	521	149	ar‐h	ar‐h	NOUN
eurjchem-1645	521	150	)	)	PUNCT
eurjchem-1645	521	151	,	,	PUNCT
eurjchem-1645	521	152	9.43	9.43	NUM
eurjchem-1645	521	153	(	(	PUNCT
eurjchem-1645	521	154	s	s	PROPN
eurjchem-1645	521	155	,	,	PUNCT
eurjchem-1645	521	156	1h	1h	NUM
eurjchem-1645	521	157	,	,	PUNCT
eurjchem-1645	521	158	ar‐h	ar‐h	NOUN
eurjchem-1645	521	159	)	)	PUNCT
eurjchem-1645	521	160	,	,	PUNCT
eurjchem-1645	521	161	14.8	14.8	NUM
eurjchem-1645	521	162	(	(	PUNCT
eurjchem-1645	521	163	br	br	PROPN
eurjchem-1645	521	164	,	,	PUNCT
eurjchem-1645	521	165	1h	1h	NUM
eurjchem-1645	521	166	,	,	PUNCT
eurjchem-1645	521	167	nh	nh	PROPN
eurjchem-1645	521	168	)	)	PUNCT
eurjchem-1645	521	169	.	.	PUNCT
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eurjchem-1645	522	2	nmr	nmr	NOUN
eurjchem-1645	522	3	(	(	PUNCT
eurjchem-1645	522	4	cdcl3	cdcl3	NOUN
eurjchem-1645	522	5	,	,	PUNCT
eurjchem-1645	522	6	100	100	NUM
eurjchem-1645	522	7	mhz	mhz	NOUN
eurjchem-1645	522	8	):	):	PUNCT
eurjchem-1645	522	9	12.22	12.22	NUM
eurjchem-1645	522	10	,	,	PUNCT
eurjchem-1645	522	11	49.44	49.44	NUM
eurjchem-1645	522	12	,	,	PUNCT
eurjchem-1645	522	13	52.46	52.46	NUM
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eurjchem-1645	522	20	,	,	PUNCT
eurjchem-1645	522	21	106.60	106.60	NUM
eurjchem-1645	522	22	,	,	PUNCT
eurjchem-1645	522	23	127.34	127.34	NUM
eurjchem-1645	522	24	,	,	PUNCT
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eurjchem-1645	522	26	,	,	PUNCT
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eurjchem-1645	522	30	,	,	PUNCT
eurjchem-1645	522	31	128.88	128.88	NUM
eurjchem-1645	522	32	,	,	PUNCT
eurjchem-1645	522	33	129.62	129.62	NUM
eurjchem-1645	522	34	,	,	PUNCT
eurjchem-1645	522	35	129.41	129.41	NUM
eurjchem-1645	522	36	,	,	PUNCT
eurjchem-1645	522	37	130.71	130.71	NUM
eurjchem-1645	522	38	,	,	PUNCT
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eurjchem-1645	522	40	,	,	PUNCT
eurjchem-1645	522	41	145.21	145.21	NUM
eurjchem-1645	522	42	,	,	PUNCT
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eurjchem-1645	522	44	,	,	PUNCT
eurjchem-1645	522	45	150.60	150.60	NUM
eurjchem-1645	522	46	,	,	PUNCT
eurjchem-1645	522	47	168.16	168.16	NUM
eurjchem-1645	522	48	.	.	PUNCT
eurjchem-1645	523	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	523	2	(	(	PUNCT
eurjchem-1645	523	3	ei	ei	PROPN
eurjchem-1645	523	4	,	,	PUNCT
eurjchem-1645	523	5	m	m	PROPN
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eurjchem-1645	523	7	z	z	NOUN
eurjchem-1645	523	8	):	):	PUNCT
eurjchem-1645	523	9	371	371	NUM
eurjchem-1645	523	10	(	(	PUNCT
eurjchem-1645	523	11	m+h	m+h	NOUN
eurjchem-1645	523	12	)	)	PUNCT
eurjchem-1645	523	13	.	.	PUNCT
eurjchem-1645	524	1	anal	anal	PROPN
eurjchem-1645	524	2	.	.	PUNCT
eurjchem-1645	524	3	calcd	calcd	NOUN
eurjchem-1645	524	4	.	.	PUNCT
eurjchem-1645	525	1	for	for	SCONJ
eurjchem-1645	525	2	c22h18n4o2	c22h18n4o2	PROPN
eurjchem-1645	525	3	:	:	PUNCT
eurjchem-1645	525	4	c	c	X
eurjchem-1645	525	5	,	,	PUNCT
eurjchem-1645	525	6	71.34	71.34	NUM
eurjchem-1645	525	7	;	;	PUNCT
eurjchem-1645	525	8	h	h	NOUN
eurjchem-1645	525	9	,	,	PUNCT
eurjchem-1645	525	10	4.90	4.90	NUM
eurjchem-1645	525	11	;	;	PUNCT
eurjchem-1645	525	12	n	n	CCONJ
eurjchem-1645	525	13	,	,	PUNCT
eurjchem-1645	525	14	15.13	15.13	NUM
eurjchem-1645	525	15	.	.	PUNCT
eurjchem-1645	525	16	found	find	VERB
eurjchem-1645	525	17	:	:	PUNCT
eurjchem-1645	526	1	c	c	X
eurjchem-1645	526	2	,	,	PUNCT
eurjchem-1645	526	3	71.32	71.32	NUM
eurjchem-1645	526	4	;	;	PUNCT
eurjchem-1645	526	5	h	h	NOUN
eurjchem-1645	526	6	,	,	PUNCT
eurjchem-1645	526	7	4.91	4.91	NUM
eurjchem-1645	526	8	;	;	PUNCT
eurjchem-1645	526	9	n	n	CCONJ
eurjchem-1645	526	10	,	,	PUNCT
eurjchem-1645	526	11	15.14	15.14	NUM
eurjchem-1645	526	12	%	%	NOUN
eurjchem-1645	526	13	.	.	PUNCT
eurjchem-1645	527	1	hplc	hplc	NOUN
eurjchem-1645	527	2	:	:	PUNCT
eurjchem-1645	527	3	r.t	r.t	PROPN
eurjchem-1645	527	4	.	.	PUNCT
eurjchem-1645	527	5	=	=	NOUN
eurjchem-1645	527	6	7.20	7.20	NUM
eurjchem-1645	527	7	min	min	NOUN
eurjchem-1645	527	8	,	,	PUNCT
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eurjchem-1645	527	10	=	=	SYM
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eurjchem-1645	527	12	%	%	NOUN
eurjchem-1645	527	13	.	.	PUNCT
eurjchem-1645	528	1	5	5	NUM
eurjchem-1645	528	2	,	,	PUNCT
eurjchem-1645	528	3	6‐dihydro‐6‐(3‐methoxyphenyl)‐3‐(quinolin‐5‐yl)‐1h‐	6‐dihydro‐6‐(3‐methoxyphenyl)‐3‐(quinolin‐5‐yl)‐1h‐	NUM
eurjchem-1645	528	4	pyrazolo[3,4‐c]pyridin‐7(4h)‐one	pyrazolo[3,4‐c]pyridin‐7(4h)‐one	NOUN
eurjchem-1645	528	5	(	(	PUNCT
eurjchem-1645	528	6	15d	15d	NUM
eurjchem-1645	528	7	):	):	PUNCT
eurjchem-1645	528	8	color	color	NOUN
eurjchem-1645	528	9	:	:	PUNCT
eurjchem-1645	528	10	off	off	ADP
eurjchem-1645	528	11	white	white	PROPN
eurjchem-1645	528	12	.	.	PUNCT
eurjchem-1645	529	1	yield	yield	NOUN
eurjchem-1645	529	2	:	:	PUNCT
eurjchem-1645	529	3	92	92	NUM
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eurjchem-1645	529	5	.	.	PUNCT
eurjchem-1645	530	1	m.p	m.p	PROPN
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eurjchem-1645	530	3	:	:	PUNCT
eurjchem-1645	531	1	206‐207	206‐207	NUM
eurjchem-1645	531	2	°	°	ADP
eurjchem-1645	531	3	c	c	PROPN
eurjchem-1645	531	4	.	.	PUNCT
eurjchem-1645	532	1	1h	1h	NUM
eurjchem-1645	532	2	nmr	nmr	NOUN
eurjchem-1645	532	3	(	(	PUNCT
eurjchem-1645	532	4	400	400	NUM
eurjchem-1645	532	5	mhz	mhz	NOUN
eurjchem-1645	532	6	,	,	PUNCT
eurjchem-1645	532	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	532	8	,	,	PUNCT
eurjchem-1645	532	9	δ	δ	PROPN
eurjchem-1645	532	10	,	,	PUNCT
eurjchem-1645	532	11	ppm	ppm	NUM
eurjchem-1645	532	12	):	):	PUNCT
eurjchem-1645	532	13	3.75	3.75	NUM
eurjchem-1645	532	14	(	(	PUNCT
eurjchem-1645	532	15	s	s	PROPN
eurjchem-1645	532	16	,	,	PUNCT
eurjchem-1645	532	17	3h	3h	NUM
eurjchem-1645	532	18	,	,	PUNCT
eurjchem-1645	532	19	o‐ch3	o‐ch3	PROPN
eurjchem-1645	532	20	)	)	PUNCT
eurjchem-1645	532	21	,	,	PUNCT
eurjchem-1645	532	22	3.80	3.80	NUM
eurjchem-1645	532	23	(	(	PUNCT
eurjchem-1645	532	24	d	d	PROPN
eurjchem-1645	532	25	,	,	PUNCT
eurjchem-1645	532	26	2h	2h	NUM
eurjchem-1645	532	27	,	,	PUNCT
eurjchem-1645	532	28	j	j	PROPN
eurjchem-1645	532	29	=	=	SYM
eurjchem-1645	532	30	7.6	7.6	NUM
eurjchem-1645	532	31	hz	hz	NOUN
eurjchem-1645	532	32	,	,	PUNCT
eurjchem-1645	532	33	ch2	ch2	PROPN
eurjchem-1645	532	34	)	)	PUNCT
eurjchem-1645	532	35	,	,	PUNCT
eurjchem-1645	532	36	4.38	4.38	NUM
eurjchem-1645	532	37	(	(	PUNCT
eurjchem-1645	532	38	d	d	PROPN
eurjchem-1645	532	39	,	,	PUNCT
eurjchem-1645	532	40	2h	2h	NUM
eurjchem-1645	532	41	,	,	PUNCT
eurjchem-1645	532	42	j	j	PROPN
eurjchem-1645	532	43	=	=	SYM
eurjchem-1645	532	44	7.8	7.8	NUM
eurjchem-1645	532	45	hz	hz	NOUN
eurjchem-1645	532	46	,	,	PUNCT
eurjchem-1645	532	47	n‐ch2	n‐ch2	PROPN
eurjchem-1645	532	48	)	)	PUNCT
eurjchem-1645	532	49	,	,	PUNCT
eurjchem-1645	532	50	6.38	6.38	NUM
eurjchem-1645	532	51	(	(	PUNCT
eurjchem-1645	532	52	t	t	PROPN
eurjchem-1645	532	53	,	,	PUNCT
eurjchem-1645	532	54	1h	1h	NUM
eurjchem-1645	532	55	,	,	PUNCT
eurjchem-1645	532	56	j	j	PROPN
eurjchem-1645	532	57	=	=	SYM
eurjchem-1645	532	58	7.6	7.6	NUM
eurjchem-1645	532	59	hz	hz	NOUN
eurjchem-1645	532	60	,	,	PUNCT
eurjchem-1645	532	61	ar‐h	ar‐h	PROPN
eurjchem-1645	532	62	)	)	PUNCT
eurjchem-1645	532	63	,	,	PUNCT
eurjchem-1645	532	64	6.58	6.58	NUM
eurjchem-1645	532	65	(	(	PUNCT
eurjchem-1645	532	66	s	s	PROPN
eurjchem-1645	532	67	,	,	PUNCT
eurjchem-1645	532	68	1h	1h	NUM
eurjchem-1645	532	69	,	,	PUNCT
eurjchem-1645	532	70	ar‐h	ar‐h	NOUN
eurjchem-1645	532	71	)	)	PUNCT
eurjchem-1645	532	72	,	,	PUNCT
eurjchem-1645	532	73	6.65	6.65	NUM
eurjchem-1645	532	74	(	(	PUNCT
eurjchem-1645	532	75	t	t	PROPN
eurjchem-1645	532	76	,	,	PUNCT
eurjchem-1645	532	77	1h	1h	NUM
eurjchem-1645	532	78	,	,	PUNCT
eurjchem-1645	532	79	j	j	PROPN
eurjchem-1645	532	80	=	=	SYM
eurjchem-1645	532	81	7.8	7.8	NUM
eurjchem-1645	532	82	hz	hz	NOUN
eurjchem-1645	532	83	,	,	PUNCT
eurjchem-1645	532	84	ar‐h	ar‐h	PROPN
eurjchem-1645	532	85	)	)	PUNCT
eurjchem-1645	532	86	,	,	PUNCT
eurjchem-1645	532	87	7.14	7.14	NUM
eurjchem-1645	532	88	(	(	PUNCT
eurjchem-1645	532	89	m	m	PROPN
eurjchem-1645	532	90	,	,	PUNCT
eurjchem-1645	532	91	1h	1h	NUM
eurjchem-1645	532	92	,	,	PUNCT
eurjchem-1645	532	93	ar‐h	ar‐h	NOUN
eurjchem-1645	532	94	)	)	PUNCT
eurjchem-1645	532	95	,	,	PUNCT
eurjchem-1645	532	96	7.88	7.88	NUM
eurjchem-1645	532	97	(	(	PUNCT
eurjchem-1645	532	98	m	m	PROPN
eurjchem-1645	532	99	,	,	PUNCT
eurjchem-1645	532	100	1h	1h	NUM
eurjchem-1645	532	101	,	,	PUNCT
eurjchem-1645	532	102	ar‐h	ar‐h	NOUN
eurjchem-1645	532	103	)	)	PUNCT
eurjchem-1645	532	104	,	,	PUNCT
eurjchem-1645	532	105	8.14‐7.98	8.14‐7.98	NUM
eurjchem-1645	532	106	(	(	PUNCT
eurjchem-1645	532	107	m	m	PROPN
eurjchem-1645	532	108	,	,	PUNCT
eurjchem-1645	532	109	3h	3h	NUM
eurjchem-1645	532	110	,	,	PUNCT
eurjchem-1645	532	111	ar‐h	ar‐h	NOUN
eurjchem-1645	532	112	)	)	PUNCT
eurjchem-1645	532	113	,	,	PUNCT
eurjchem-1645	532	114	8.37‐8.33	8.37‐8.33	PROPN
eurjchem-1645	532	115	(	(	PUNCT
eurjchem-1645	532	116	d	d	PROPN
eurjchem-1645	532	117	,	,	PUNCT
eurjchem-1645	532	118	1h	1h	NUM
eurjchem-1645	532	119	,	,	PUNCT
eurjchem-1645	532	120	j	j	PROPN
eurjchem-1645	532	121	=	=	SYM
eurjchem-1645	532	122	7.8	7.8	NUM
eurjchem-1645	532	123	hz	hz	NOUN
eurjchem-1645	532	124	,	,	PUNCT
eurjchem-1645	532	125	ar‐	ar‐	PROPN
eurjchem-1645	532	126	h	h	NOUN
eurjchem-1645	532	127	)	)	PUNCT
eurjchem-1645	532	128	,	,	PUNCT
eurjchem-1645	532	129	9.16	9.16	NUM
eurjchem-1645	532	130	(	(	PUNCT
eurjchem-1645	532	131	s	s	PROPN
eurjchem-1645	532	132	,	,	PUNCT
eurjchem-1645	532	133	1h	1h	NUM
eurjchem-1645	532	134	,	,	PUNCT
eurjchem-1645	532	135	ar‐h	ar‐h	NOUN
eurjchem-1645	532	136	)	)	PUNCT
eurjchem-1645	532	137	,	,	PUNCT
eurjchem-1645	532	138	12.9	12.9	NUM
eurjchem-1645	532	139	(	(	PUNCT
eurjchem-1645	532	140	s	s	PROPN
eurjchem-1645	532	141	,	,	PUNCT
eurjchem-1645	532	142	1h	1h	NUM
eurjchem-1645	532	143	,	,	PUNCT
eurjchem-1645	532	144	nh	nh	PROPN
eurjchem-1645	532	145	)	)	PUNCT
eurjchem-1645	532	146	.	.	PUNCT
eurjchem-1645	533	1	13c	13c	NOUN
eurjchem-1645	533	2	nmr	nmr	NOUN
eurjchem-1645	533	3	(	(	PUNCT
eurjchem-1645	533	4	100	100	NUM
eurjchem-1645	533	5	mhz	mhz	NOUN
eurjchem-1645	533	6	,	,	PUNCT
eurjchem-1645	533	7	cdcl3	cdcl3	PROPN
eurjchem-1645	533	8	,	,	PUNCT
eurjchem-1645	533	9	δ	δ	PROPN
eurjchem-1645	533	10	,	,	PUNCT
eurjchem-1645	533	11	ppm	ppm	NOUN
eurjchem-1645	533	12	):	):	PUNCT
eurjchem-1645	533	13	12.62	12.62	NUM
eurjchem-1645	533	14	,	,	PUNCT
eurjchem-1645	533	15	49.44	49.44	NUM
eurjchem-1645	533	16	,	,	PUNCT
eurjchem-1645	533	17	52.56	52.56	NUM
eurjchem-1645	533	18	,	,	PUNCT
eurjchem-1645	533	19	54.46	54.46	NUM
eurjchem-1645	533	20	,	,	PUNCT
eurjchem-1645	533	21	97.76	97.76	NUM
eurjchem-1645	533	22	,	,	PUNCT
eurjchem-1645	533	23	102.31	102.31	NUM
eurjchem-1645	533	24	,	,	PUNCT
eurjchem-1645	533	25	106.76	106.76	NUM
eurjchem-1645	533	26	,	,	PUNCT
eurjchem-1645	533	27	127.44	127.44	NUM
eurjchem-1645	533	28	,	,	PUNCT
eurjchem-1645	533	29	127.84	127.84	NUM
eurjchem-1645	533	30	,	,	PUNCT
eurjchem-1645	533	31	128.32	128.32	NUM
eurjchem-1645	533	32	,	,	PUNCT
eurjchem-1645	533	33	128.42	128.42	NUM
eurjchem-1645	533	34	,	,	PUNCT
eurjchem-1645	533	35	128.88	128.88	NUM
eurjchem-1645	533	36	,	,	PUNCT
eurjchem-1645	533	37	129.42	129.42	NUM
eurjchem-1645	533	38	,	,	PUNCT
eurjchem-1645	533	39	129.40	129.40	NUM
eurjchem-1645	533	40	,	,	PUNCT
eurjchem-1645	533	41	130.60	130.60	NUM
eurjchem-1645	533	42	,	,	PUNCT
eurjchem-1645	533	43	130.85	130.85	NUM
eurjchem-1645	533	44	,	,	PUNCT
eurjchem-1645	533	45	145.31	145.31	NUM
eurjchem-1645	533	46	,	,	PUNCT
eurjchem-1645	533	47	148.63	148.63	NUM
eurjchem-1645	533	48	,	,	PUNCT
eurjchem-1645	533	49	152.14	152.14	NUM
eurjchem-1645	533	50	,	,	PUNCT
eurjchem-1645	533	51	168.60	168.60	NUM
eurjchem-1645	533	52	.	.	PUNCT
eurjchem-1645	534	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	534	2	(	(	PUNCT
eurjchem-1645	534	3	ei	ei	PROPN
eurjchem-1645	534	4	,	,	PUNCT
eurjchem-1645	534	5	m	m	PROPN
eurjchem-1645	534	6	/	/	SYM
eurjchem-1645	534	7	z	z	NOUN
eurjchem-1645	534	8	):	):	PUNCT
eurjchem-1645	534	9	371	371	NUM
eurjchem-1645	534	10	(	(	PUNCT
eurjchem-1645	534	11	m+h	m+h	NOUN
eurjchem-1645	534	12	)	)	PUNCT
eurjchem-1645	534	13	.	.	PUNCT
eurjchem-1645	535	1	anal	anal	PROPN
eurjchem-1645	535	2	.	.	PUNCT
eurjchem-1645	535	3	calcd	calcd	NOUN
eurjchem-1645	535	4	.	.	PUNCT
eurjchem-1645	536	1	for	for	SCONJ
eurjchem-1645	536	2	c22h18n4o2	c22h18n4o2	PROPN
eurjchem-1645	536	3	:	:	PUNCT
eurjchem-1645	536	4	c	c	X
eurjchem-1645	536	5	,	,	PUNCT
eurjchem-1645	536	6	71.34	71.34	NUM
eurjchem-1645	536	7	;	;	PUNCT
eurjchem-1645	536	8	h	h	NOUN
eurjchem-1645	536	9	,	,	PUNCT
eurjchem-1645	536	10	4.90	4.90	NUM
eurjchem-1645	536	11	;	;	PUNCT
eurjchem-1645	536	12	n	n	CCONJ
eurjchem-1645	536	13	,	,	PUNCT
eurjchem-1645	536	14	15.13	15.13	NUM
eurjchem-1645	536	15	.	.	PUNCT
eurjchem-1645	536	16	found	find	VERB
eurjchem-1645	536	17	:	:	PUNCT
eurjchem-1645	537	1	c	c	X
eurjchem-1645	537	2	,	,	PUNCT
eurjchem-1645	537	3	71.31	71.31	NUM
eurjchem-1645	537	4	;	;	PUNCT
eurjchem-1645	537	5	h	h	NOUN
eurjchem-1645	537	6	,	,	PUNCT
eurjchem-1645	537	7	4.92	4.92	NUM
eurjchem-1645	537	8	;	;	PUNCT
eurjchem-1645	537	9	n	n	CCONJ
eurjchem-1645	537	10	,	,	PUNCT
eurjchem-1645	537	11	15.11	15.11	NUM
eurjchem-1645	537	12	%	%	NOUN
eurjchem-1645	537	13	.	.	PUNCT
eurjchem-1645	538	1	hplc	hplc	NOUN
eurjchem-1645	538	2	:	:	PUNCT
eurjchem-1645	538	3	r.t	r.t	PROPN
eurjchem-1645	538	4	.	.	PUNCT
eurjchem-1645	538	5	=	=	NOUN
eurjchem-1645	539	1	7.81	7.81	NUM
eurjchem-1645	539	2	min	min	NOUN
eurjchem-1645	539	3	,	,	PUNCT
eurjchem-1645	539	4	purity	purity	NOUN
eurjchem-1645	539	5	=	=	NOUN
eurjchem-1645	539	6	96.1	96.1	NUM
eurjchem-1645	539	7	%	%	NOUN
eurjchem-1645	539	8	.	.	PUNCT
eurjchem-1645	540	1	3‐(benzofuran‐2‐yl)‐5,6‐dihydro‐6‐(pyrimidin‐2‐yl)‐1h‐pyra	3‐(benzofuran‐2‐yl)‐5,6‐dihydro‐6‐(pyrimidin‐2‐yl)‐1h‐pyra	NUM
eurjchem-1645	540	2	zolo[3,4‐c]pyridin‐7(4h)‐one	zolo[3,4‐c]pyridin‐7(4h)‐one	NOUN
eurjchem-1645	540	3	(	(	PUNCT
eurjchem-1645	540	4	15e	15e	NUM
eurjchem-1645	540	5	):	):	PUNCT
eurjchem-1645	540	6	color	color	NOUN
eurjchem-1645	540	7	:	:	PUNCT
eurjchem-1645	540	8	yellow	yellow	ADJ
eurjchem-1645	540	9	.	.	PUNCT
eurjchem-1645	541	1	yield	yield	NOUN
eurjchem-1645	541	2	:	:	PUNCT
eurjchem-1645	541	3	79	79	NUM
eurjchem-1645	541	4	%	%	NOUN
eurjchem-1645	541	5	.	.	PUNCT
eurjchem-1645	542	1	m.p	m.p	PROPN
eurjchem-1645	542	2	.	.	PROPN
eurjchem-1645	542	3	:	:	PUNCT
eurjchem-1645	543	1	176‐177	176‐177	NUM
eurjchem-1645	543	2	°	°	SYM
eurjchem-1645	543	3	c	c	X
eurjchem-1645	543	4	.	.	PUNCT
eurjchem-1645	544	1	1h	1h	NUM
eurjchem-1645	544	2	nmr	nmr	NOUN
eurjchem-1645	544	3	(	(	PUNCT
eurjchem-1645	544	4	400	400	NUM
eurjchem-1645	544	5	mhz	mhz	NOUN
eurjchem-1645	544	6	,	,	PUNCT
eurjchem-1645	544	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	544	8	,	,	PUNCT
eurjchem-1645	544	9	δ	δ	PROPN
eurjchem-1645	544	10	,	,	PUNCT
eurjchem-1645	544	11	ppm	ppm	NUM
eurjchem-1645	544	12	):	):	PUNCT
eurjchem-1645	544	13	3.22	3.22	NUM
eurjchem-1645	544	14	(	(	PUNCT
eurjchem-1645	544	15	q	q	NOUN
eurjchem-1645	544	16	,	,	PUNCT
eurjchem-1645	544	17	2h	2h	NUM
eurjchem-1645	544	18	,	,	PUNCT
eurjchem-1645	544	19	ch2	ch2	PROPN
eurjchem-1645	544	20	)	)	PUNCT
eurjchem-1645	544	21	,	,	PUNCT
eurjchem-1645	544	22	4.24	4.24	NUM
eurjchem-1645	544	23	(	(	PUNCT
eurjchem-1645	544	24	d	d	PROPN
eurjchem-1645	544	25	,	,	PUNCT
eurjchem-1645	544	26	2h	2h	NUM
eurjchem-1645	544	27	,	,	PUNCT
eurjchem-1645	544	28	j	j	PROPN
eurjchem-1645	544	29	=	=	PROPN
eurjchem-1645	544	30	8.2	8.2	NUM
eurjchem-1645	544	31	hz	hz	NOUN
eurjchem-1645	544	32	,	,	PUNCT
eurjchem-1645	544	33	n‐ch2	n‐ch2	PROPN
eurjchem-1645	544	34	)	)	PUNCT
eurjchem-1645	544	35	,	,	PUNCT
eurjchem-1645	544	36	7.41‐7.16	7.41‐7.16	NUM
eurjchem-1645	544	37	(	(	PUNCT
eurjchem-1645	544	38	m	m	PROPN
eurjchem-1645	544	39	4h	4h	NUM
eurjchem-1645	544	40	,	,	PUNCT
eurjchem-1645	544	41	ar‐h	ar‐h	NOUN
eurjchem-1645	544	42	)	)	PUNCT
eurjchem-1645	544	43	,	,	PUNCT
eurjchem-1645	544	44	7.78‐7.61	7.78‐7.61	NUM
eurjchem-1645	544	45	(	(	PUNCT
eurjchem-1645	544	46	m	m	PROPN
eurjchem-1645	544	47	,	,	PUNCT
eurjchem-1645	544	48	2h	2h	NUM
eurjchem-1645	544	49	,	,	PUNCT
eurjchem-1645	544	50	ar‐h	ar‐h	NOUN
eurjchem-1645	544	51	)	)	PUNCT
eurjchem-1645	544	52	,	,	PUNCT
eurjchem-1645	544	53	8.84	8.84	NUM
eurjchem-1645	544	54	(	(	PUNCT
eurjchem-1645	544	55	d	d	PROPN
eurjchem-1645	544	56	,	,	PUNCT
eurjchem-1645	544	57	2h	2h	NUM
eurjchem-1645	544	58	,	,	PUNCT
eurjchem-1645	544	59	j	j	PROPN
eurjchem-1645	544	60	=	=	SYM
eurjchem-1645	544	61	7.8	7.8	NUM
eurjchem-1645	544	62	hz	hz	NOUN
eurjchem-1645	544	63	,	,	PUNCT
eurjchem-1645	544	64	ar‐h	ar‐h	PROPN
eurjchem-1645	544	65	)	)	PUNCT
eurjchem-1645	544	66	,	,	PUNCT
eurjchem-1645	544	67	14.4	14.4	NUM
eurjchem-1645	544	68	(	(	PUNCT
eurjchem-1645	544	69	br	br	PROPN
eurjchem-1645	544	70	,	,	PUNCT
eurjchem-1645	544	71	1h	1h	NUM
eurjchem-1645	544	72	,	,	PUNCT
eurjchem-1645	544	73	nh	nh	PROPN
eurjchem-1645	544	74	)	)	PUNCT
eurjchem-1645	544	75	.	.	PUNCT
eurjchem-1645	545	1	13c	13c	NOUN
eurjchem-1645	545	2	nmr	nmr	NOUN
eurjchem-1645	545	3	(	(	PUNCT
eurjchem-1645	545	4	100	100	NUM
eurjchem-1645	545	5	mhz	mhz	NOUN
eurjchem-1645	545	6	,	,	PUNCT
eurjchem-1645	545	7	cdcl3	cdcl3	PROPN
eurjchem-1645	545	8	,	,	PUNCT
eurjchem-1645	545	9	δ	δ	PROPN
eurjchem-1645	545	10	,	,	PUNCT
eurjchem-1645	545	11	ppm	ppm	NOUN
eurjchem-1645	545	12	):	):	PUNCT
eurjchem-1645	545	13	10.24	10.24	NUM
eurjchem-1645	545	14	,	,	PUNCT
eurjchem-1645	545	15	43.92	43.92	NUM
eurjchem-1645	545	16	,	,	PUNCT
eurjchem-1645	545	17	102.84	102.84	NUM
eurjchem-1645	545	18	,	,	PUNCT
eurjchem-1645	545	19	110.36	110.36	NUM
eurjchem-1645	545	20	,	,	PUNCT
eurjchem-1645	545	21	111.62	111.62	NUM
eurjchem-1645	545	22	,	,	PUNCT
eurjchem-1645	545	23	116.21	116.21	NUM
eurjchem-1645	545	24	,	,	PUNCT
eurjchem-1645	545	25	121.26	121.26	NUM
eurjchem-1645	545	26	,	,	PUNCT
eurjchem-1645	545	27	123.36	123.36	NUM
eurjchem-1645	545	28	,	,	PUNCT
eurjchem-1645	545	29	124.82	124.82	NUM
eurjchem-1645	545	30	,	,	PUNCT
eurjchem-1645	545	31	133.11	133.11	NUM
eurjchem-1645	545	32	,	,	PUNCT
eurjchem-1645	545	33	133.26	133.26	NUM
eurjchem-1645	545	34	,	,	PUNCT
eurjchem-1645	545	35	150.45	150.45	NUM
eurjchem-1645	545	36	,	,	PUNCT
eurjchem-1645	545	37	156.46	156.46	NUM
eurjchem-1645	545	38	,	,	PUNCT
eurjchem-1645	545	39	158.10	158.10	NUM
eurjchem-1645	545	40	,	,	PUNCT
eurjchem-1645	545	41	169.32	169.32	NUM
eurjchem-1645	545	42	.	.	PUNCT
eurjchem-1645	546	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	546	2	(	(	PUNCT
eurjchem-1645	546	3	ei	ei	PROPN
eurjchem-1645	546	4	,	,	PUNCT
eurjchem-1645	546	5	m	m	PROPN
eurjchem-1645	546	6	/	/	SYM
eurjchem-1645	546	7	z	z	PROPN
eurjchem-1645	546	8	):	):	PUNCT
eurjchem-1645	546	9	332	332	NUM
eurjchem-1645	546	10	(	(	PUNCT
eurjchem-1645	546	11	m+h	m+h	PROPN
eurjchem-1645	546	12	)	)	PUNCT
eurjchem-1645	546	13	.	.	PUNCT
eurjchem-1645	547	1	anal	anal	PROPN
eurjchem-1645	547	2	.	.	PUNCT
eurjchem-1645	547	3	calcd	calcd	NOUN
eurjchem-1645	547	4	.	.	PUNCT
eurjchem-1645	548	1	for	for	ADP
eurjchem-1645	548	2	c18h13n5o2	c18h13n5o2	PROPN
eurjchem-1645	548	3	:	:	PUNCT
eurjchem-1645	548	4	c	c	X
eurjchem-1645	548	5	,	,	PUNCT
eurjchem-1645	548	6	65.25	65.25	NUM
eurjchem-1645	548	7	;	;	PUNCT
eurjchem-1645	548	8	h	h	NOUN
eurjchem-1645	548	9	,	,	PUNCT
eurjchem-1645	548	10	3.95	3.95	NUM
eurjchem-1645	548	11	;	;	PUNCT
eurjchem-1645	548	12	n	n	CCONJ
eurjchem-1645	548	13	,	,	PUNCT
eurjchem-1645	548	14	21.14	21.14	NUM
eurjchem-1645	548	15	.	.	PUNCT
eurjchem-1645	548	16	found	find	VERB
eurjchem-1645	548	17	:	:	PUNCT
eurjchem-1645	549	1	c	c	X
eurjchem-1645	549	2	,	,	PUNCT
eurjchem-1645	549	3	65.23	65.23	NUM
eurjchem-1645	549	4	;	;	PUNCT
eurjchem-1645	549	5	h	h	NOUN
eurjchem-1645	549	6	,	,	PUNCT
eurjchem-1645	549	7	3.97	3.97	NUM
eurjchem-1645	549	8	;	;	PUNCT
eurjchem-1645	549	9	n	n	CCONJ
eurjchem-1645	549	10	,	,	PUNCT
eurjchem-1645	549	11	21.15	21.15	NUM
eurjchem-1645	549	12	%	%	NOUN
eurjchem-1645	549	13	.	.	PUNCT
eurjchem-1645	550	1	hplc	hplc	NOUN
eurjchem-1645	550	2	:	:	PUNCT
eurjchem-1645	550	3	r.t	r.t	PROPN
eurjchem-1645	550	4	.	.	PUNCT
eurjchem-1645	550	5	=	=	NOUN
eurjchem-1645	551	1	5.17	5.17	NUM
eurjchem-1645	551	2	min	min	NOUN
eurjchem-1645	551	3	,	,	PUNCT
eurjchem-1645	551	4	purity	purity	NOUN
eurjchem-1645	551	5	=	=	NOUN
eurjchem-1645	551	6	99.6	99.6	NUM
eurjchem-1645	551	7	%	%	NOUN
eurjchem-1645	551	8	.	.	PUNCT
eurjchem-1645	552	1	3‐(benzo[b]thiophen‐2‐yl)‐5	3‐(benzo[b]thiophen‐2‐yl)‐5	NUM
eurjchem-1645	552	2	,	,	PUNCT
eurjchem-1645	552	3	6‐dihydro‐6‐(pyrimidin‐2‐yl)‐	6‐dihydro‐6‐(pyrimidin‐2‐yl)‐	PROPN
eurjchem-1645	552	4	1h‐pyrazolo[3,4‐c]pyridin‐7(4h)‐one	1h‐pyrazolo[3,4‐c]pyridin‐7(4h)‐one	NUM
eurjchem-1645	552	5	(	(	PUNCT
eurjchem-1645	552	6	15f	15f	PROPN
eurjchem-1645	552	7	):	):	PUNCT
eurjchem-1645	552	8	color	color	NOUN
eurjchem-1645	552	9	:	:	PUNCT
eurjchem-1645	552	10	yellow	yellow	ADJ
eurjchem-1645	552	11	.	.	PUNCT
eurjchem-1645	553	1	yield	yield	NOUN
eurjchem-1645	553	2	:	:	PUNCT
eurjchem-1645	553	3	84	84	NUM
eurjchem-1645	553	4	%	%	NOUN
eurjchem-1645	553	5	.	.	PUNCT
eurjchem-1645	554	1	m.p	m.p	PROPN
eurjchem-1645	554	2	.	.	PROPN
eurjchem-1645	554	3	:	:	PUNCT
eurjchem-1645	555	1	202‐203	202‐203	NUM
eurjchem-1645	555	2	°	°	SYM
eurjchem-1645	555	3	c	c	NOUN
eurjchem-1645	555	4	.	.	PUNCT
eurjchem-1645	555	5	1h	1h	NUM
eurjchem-1645	555	6	nmr	nmr	NOUN
eurjchem-1645	555	7	(	(	PUNCT
eurjchem-1645	555	8	400	400	NUM
eurjchem-1645	555	9	mhz	mhz	NOUN
eurjchem-1645	555	10	,	,	PUNCT
eurjchem-1645	555	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	555	12	,	,	PUNCT
eurjchem-1645	555	13	δ	δ	PROPN
eurjchem-1645	555	14	,	,	PUNCT
eurjchem-1645	555	15	ppm	ppm	NUM
eurjchem-1645	555	16	):	):	PUNCT
eurjchem-1645	555	17	3.48	3.48	NUM
eurjchem-1645	555	18	(	(	PUNCT
eurjchem-1645	555	19	q	q	NOUN
eurjchem-1645	555	20	,	,	PUNCT
eurjchem-1645	555	21	2h	2h	NUM
eurjchem-1645	555	22	,	,	PUNCT
eurjchem-1645	555	23	ch2	ch2	PROPN
eurjchem-1645	555	24	)	)	PUNCT
eurjchem-1645	555	25	,	,	PUNCT
eurjchem-1645	555	26	4.44	4.44	NUM
eurjchem-1645	555	27	(	(	PUNCT
eurjchem-1645	555	28	d	d	PROPN
eurjchem-1645	555	29	,	,	PUNCT
eurjchem-1645	555	30	2h	2h	NUM
eurjchem-1645	555	31	,	,	PUNCT
eurjchem-1645	555	32	j	j	PROPN
eurjchem-1645	555	33	=	=	PROPN
eurjchem-1645	555	34	8.2	8.2	NUM
eurjchem-1645	555	35	hz	hz	NOUN
eurjchem-1645	555	36	,	,	PUNCT
eurjchem-1645	555	37	n‐ch2	n‐ch2	PROPN
eurjchem-1645	555	38	)	)	PUNCT
eurjchem-1645	555	39	,	,	PUNCT
eurjchem-1645	555	40	7.48‐	7.48‐	NUM
eurjchem-1645	555	41	7.16	7.16	NUM
eurjchem-1645	555	42	(	(	PUNCT
eurjchem-1645	555	43	m	m	PROPN
eurjchem-1645	555	44	4h	4h	NUM
eurjchem-1645	555	45	,	,	PUNCT
eurjchem-1645	555	46	ar‐h	ar‐h	NOUN
eurjchem-1645	555	47	)	)	PUNCT
eurjchem-1645	555	48	,	,	PUNCT
eurjchem-1645	555	49	7.78‐7.38	7.78‐7.38	PROPN
eurjchem-1645	555	50	(	(	PUNCT
eurjchem-1645	555	51	m	m	PROPN
eurjchem-1645	555	52	,	,	PUNCT
eurjchem-1645	555	53	2h	2h	NUM
eurjchem-1645	555	54	,	,	PUNCT
eurjchem-1645	555	55	ar‐h	ar‐h	NOUN
eurjchem-1645	555	56	)	)	PUNCT
eurjchem-1645	555	57	,	,	PUNCT
eurjchem-1645	555	58	8.84	8.84	NUM
eurjchem-1645	555	59	(	(	PUNCT
eurjchem-1645	555	60	d	d	PROPN
eurjchem-1645	555	61	,	,	PUNCT
eurjchem-1645	555	62	2h	2h	NUM
eurjchem-1645	555	63	,	,	PUNCT
eurjchem-1645	555	64	j	j	PROPN
eurjchem-1645	555	65	=	=	SYM
eurjchem-1645	555	66	7.6	7.6	NUM
eurjchem-1645	555	67	hz	hz	NOUN
eurjchem-1645	555	68	,	,	PUNCT
eurjchem-1645	555	69	ar‐h	ar‐h	PROPN
eurjchem-1645	555	70	)	)	PUNCT
eurjchem-1645	555	71	,	,	PUNCT
eurjchem-1645	555	72	14.3	14.3	NUM
eurjchem-1645	555	73	(	(	PUNCT
eurjchem-1645	555	74	br	br	PROPN
eurjchem-1645	555	75	,	,	PUNCT
eurjchem-1645	555	76	1h	1h	NUM
eurjchem-1645	555	77	,	,	PUNCT
eurjchem-1645	555	78	nh	nh	PROPN
eurjchem-1645	555	79	)	)	PUNCT
eurjchem-1645	555	80	.	.	PUNCT
eurjchem-1645	556	1	13c	13c	NOUN
eurjchem-1645	556	2	nmr	nmr	NOUN
eurjchem-1645	556	3	(	(	PUNCT
eurjchem-1645	556	4	100	100	NUM
eurjchem-1645	556	5	mhz	mhz	NOUN
eurjchem-1645	556	6	,	,	PUNCT
eurjchem-1645	556	7	cdcl3	cdcl3	PROPN
eurjchem-1645	556	8	,	,	PUNCT
eurjchem-1645	556	9	δ	δ	PROPN
eurjchem-1645	556	10	,	,	PUNCT
eurjchem-1645	556	11	ppm	ppm	NOUN
eurjchem-1645	556	12	):	):	PUNCT
eurjchem-1645	556	13	10.24	10.24	NUM
eurjchem-1645	556	14	,	,	PUNCT
eurjchem-1645	556	15	43.92	43.92	NUM
eurjchem-1645	556	16	,	,	PUNCT
eurjchem-1645	556	17	102.84	102.84	NUM
eurjchem-1645	556	18	,	,	PUNCT
eurjchem-1645	556	19	110.36	110.36	NUM
eurjchem-1645	556	20	,	,	PUNCT
eurjchem-1645	556	21	111.62	111.62	NUM
eurjchem-1645	556	22	,	,	PUNCT
eurjchem-1645	556	23	116.21	116.21	NUM
eurjchem-1645	556	24	,	,	PUNCT
eurjchem-1645	556	25	121.26	121.26	NUM
eurjchem-1645	556	26	,	,	PUNCT
eurjchem-1645	556	27	123.36	123.36	NUM
eurjchem-1645	556	28	,	,	PUNCT
eurjchem-1645	556	29	124.82	124.82	NUM
eurjchem-1645	556	30	,	,	PUNCT
eurjchem-1645	556	31	133.11	133.11	NUM
eurjchem-1645	556	32	,	,	PUNCT
eurjchem-1645	556	33	133.26	133.26	NUM
eurjchem-1645	556	34	,	,	PUNCT
eurjchem-1645	556	35	150.45	150.45	NUM
eurjchem-1645	556	36	,	,	PUNCT
eurjchem-1645	556	37	156.46	156.46	NUM
eurjchem-1645	556	38	,	,	PUNCT
eurjchem-1645	556	39	158.10	158.10	NUM
eurjchem-1645	556	40	,	,	PUNCT
eurjchem-1645	556	41	169.32	169.32	NUM
eurjchem-1645	556	42	.	.	PUNCT
eurjchem-1645	557	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	557	2	(	(	PUNCT
eurjchem-1645	557	3	ei	ei	PROPN
eurjchem-1645	557	4	,	,	PUNCT
eurjchem-1645	557	5	m	m	PROPN
eurjchem-1645	557	6	/	/	SYM
eurjchem-1645	557	7	z	z	NOUN
eurjchem-1645	557	8	):	):	PUNCT
eurjchem-1645	557	9	347	347	NUM
eurjchem-1645	557	10	(	(	PUNCT
eurjchem-1645	557	11	m+h	m+h	NOUN
eurjchem-1645	557	12	)	)	PUNCT
eurjchem-1645	557	13	.	.	PUNCT
eurjchem-1645	558	1	anal	anal	PROPN
eurjchem-1645	558	2	.	.	PUNCT
eurjchem-1645	558	3	calcd	calcd	NOUN
eurjchem-1645	558	4	.	.	PUNCT
eurjchem-1645	559	1	for	for	ADP
eurjchem-1645	559	2	c18h13n5os	c18h13n5o	NOUN
eurjchem-1645	559	3	:	:	PUNCT
eurjchem-1645	559	4	c	c	X
eurjchem-1645	559	5	,	,	PUNCT
eurjchem-1645	559	6	62.23	62.23	NUM
eurjchem-1645	559	7	;	;	PUNCT
eurjchem-1645	559	8	h	h	X
eurjchem-1645	559	9	,	,	PUNCT
eurjchem-1645	559	10	3.77	3.77	NUM
eurjchem-1645	559	11	;	;	PUNCT
eurjchem-1645	559	12	n	n	CCONJ
eurjchem-1645	559	13	,	,	PUNCT
eurjchem-1645	559	14	20.16	20.16	NUM
eurjchem-1645	559	15	.	.	PUNCT
eurjchem-1645	559	16	found	find	VERB
eurjchem-1645	559	17	:	:	PUNCT
eurjchem-1645	559	18	c	c	X
eurjchem-1645	559	19	,	,	PUNCT
eurjchem-1645	559	20	62.21	62.21	NUM
eurjchem-1645	559	21	;	;	PUNCT
eurjchem-1645	560	1	h	h	NOUN
eurjchem-1645	560	2	,	,	PUNCT
eurjchem-1645	560	3	3.76	3.76	NUM
eurjchem-1645	560	4	;	;	PUNCT
eurjchem-1645	560	5	n	n	CCONJ
eurjchem-1645	560	6	,	,	PUNCT
eurjchem-1645	560	7	20.18	20.18	NUM
eurjchem-1645	560	8	%	%	NOUN
eurjchem-1645	560	9	.	.	PUNCT
eurjchem-1645	561	1	hplc	hplc	NOUN
eurjchem-1645	561	2	:	:	PUNCT
eurjchem-1645	561	3	r.t	r.t	PROPN
eurjchem-1645	561	4	.	.	PUNCT
eurjchem-1645	562	1	=	=	PROPN
eurjchem-1645	562	2	8.12	8.12	NUM
eurjchem-1645	562	3	min	min	NOUN
eurjchem-1645	562	4	,	,	PUNCT
eurjchem-1645	562	5	purity	purity	NOUN
eurjchem-1645	562	6	=	=	NOUN
eurjchem-1645	562	7	98.1	98.1	NUM
eurjchem-1645	562	8	%	%	NOUN
eurjchem-1645	562	9	.	.	PUNCT
eurjchem-1645	563	1	5	5	NUM
eurjchem-1645	563	2	,	,	PUNCT
eurjchem-1645	563	3	6‐dihydro‐6‐(pyrimidin‐2‐yl)‐3‐(quinolin‐3‐yl)‐1h‐pyra	6‐dihydro‐6‐(pyrimidin‐2‐yl)‐3‐(quinolin‐3‐yl)‐1h‐pyra	NUM
eurjchem-1645	563	4	zolo[3,4‐c]pyridin‐7(4h)‐one	zolo[3,4‐c]pyridin‐7(4h)‐one	NOUN
eurjchem-1645	563	5	(	(	PUNCT
eurjchem-1645	563	6	15	15	NUM
eurjchem-1645	563	7	g	g	NOUN
eurjchem-1645	563	8	):	):	PUNCT
eurjchem-1645	563	9	color	color	NOUN
eurjchem-1645	563	10	:	:	PUNCT
eurjchem-1645	563	11	white	white	ADJ
eurjchem-1645	563	12	.	.	PUNCT
eurjchem-1645	564	1	yield	yield	NOUN
eurjchem-1645	564	2	:	:	PUNCT
eurjchem-1645	564	3	85	85	NUM
eurjchem-1645	564	4	%	%	NOUN
eurjchem-1645	564	5	.	.	PUNCT
eurjchem-1645	565	1	m.p	m.p	PROPN
eurjchem-1645	565	2	.	.	PROPN
eurjchem-1645	565	3	:	:	PUNCT
eurjchem-1645	566	1	211‐212	211‐212	NUM
eurjchem-1645	566	2	°	°	ADP
eurjchem-1645	566	3	c	c	PROPN
eurjchem-1645	566	4	.	.	PUNCT
eurjchem-1645	566	5	1h	1h	NUM
eurjchem-1645	566	6	nmr	nmr	NOUN
eurjchem-1645	566	7	(	(	PUNCT
eurjchem-1645	566	8	400	400	NUM
eurjchem-1645	566	9	mhz	mhz	NOUN
eurjchem-1645	566	10	,	,	PUNCT
eurjchem-1645	566	11	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	566	12	,	,	PUNCT
eurjchem-1645	566	13	δ	δ	PROPN
eurjchem-1645	566	14	,	,	PUNCT
eurjchem-1645	566	15	ppm	ppm	NOUN
eurjchem-1645	566	16	):	):	PUNCT
eurjchem-1645	566	17	3.26	3.26	NUM
eurjchem-1645	566	18	(	(	PUNCT
eurjchem-1645	566	19	q	q	NOUN
eurjchem-1645	566	20	,	,	PUNCT
eurjchem-1645	566	21	2h	2h	NUM
eurjchem-1645	566	22	,	,	PUNCT
eurjchem-1645	566	23	j=	j=	X
eurjchem-1645	566	24	7.6	7.6	NUM
eurjchem-1645	566	25	hz	hz	VERB
eurjchem-1645	566	26	,	,	PUNCT
eurjchem-1645	566	27	ch2	ch2	PROPN
eurjchem-1645	566	28	)	)	PUNCT
eurjchem-1645	566	29	,	,	PUNCT
eurjchem-1645	566	30	4.26	4.26	NUM
eurjchem-1645	566	31	(	(	PUNCT
eurjchem-1645	566	32	t	t	PROPN
eurjchem-1645	566	33	,	,	PUNCT
eurjchem-1645	566	34	2h	2h	NUM
eurjchem-1645	566	35	,	,	PUNCT
eurjchem-1645	566	36	j	j	PROPN
eurjchem-1645	567	1	=	=	SYM
eurjchem-1645	567	2	7.6	7.6	NUM
eurjchem-1645	567	3	hz	hz	NOUN
eurjchem-1645	567	4	,	,	PUNCT
eurjchem-1645	567	5	n‐ch2	n‐ch2	PROPN
eurjchem-1645	567	6	)	)	PUNCT
eurjchem-1645	567	7	,	,	PUNCT
eurjchem-1645	567	8	7.38	7.38	NUM
eurjchem-1645	567	9	(	(	PUNCT
eurjchem-1645	567	10	t	t	PROPN
eurjchem-1645	567	11	,	,	PUNCT
eurjchem-1645	567	12	1h	1h	NUM
eurjchem-1645	567	13	,	,	PUNCT
eurjchem-1645	567	14	j	j	PROPN
eurjchem-1645	567	15	=	=	SYM
eurjchem-1645	567	16	7.6	7.6	NUM
eurjchem-1645	567	17	hz	hz	NOUN
eurjchem-1645	567	18	,	,	PUNCT
eurjchem-1645	567	19	ar‐h	ar‐h	PROPN
eurjchem-1645	567	20	)	)	PUNCT
eurjchem-1645	567	21	,	,	PUNCT
eurjchem-1645	567	22	7.6	7.6	NUM
eurjchem-1645	567	23	(	(	PUNCT
eurjchem-1645	567	24	q	q	NOUN
eurjchem-1645	567	25	,	,	PUNCT
eurjchem-1645	567	26	1h	1h	NUM
eurjchem-1645	567	27	,	,	PUNCT
eurjchem-1645	567	28	j	j	PROPN
eurjchem-1645	567	29	=	=	PROPN
eurjchem-1645	567	30	8.2	8.2	NUM
eurjchem-1645	567	31	hz	hz	ADJ
eurjchem-1645	567	32	,	,	PUNCT
eurjchem-1645	567	33	ar‐h	ar‐h	PROPN
eurjchem-1645	567	34	)	)	PUNCT
eurjchem-1645	567	35	,	,	PUNCT
eurjchem-1645	567	36	7.80	7.80	NUM
eurjchem-1645	567	37	(	(	PUNCT
eurjchem-1645	567	38	t	t	PROPN
eurjchem-1645	567	39	,	,	PUNCT
eurjchem-1645	567	40	1h	1h	NUM
eurjchem-1645	567	41	,	,	PUNCT
eurjchem-1645	567	42	j	j	PROPN
eurjchem-1645	567	43	=	=	PROPN
eurjchem-1645	567	44	8.2	8.2	NUM
eurjchem-1645	567	45	hz	hz	ADJ
eurjchem-1645	567	46	,	,	PUNCT
eurjchem-1645	567	47	ar‐h	ar‐h	NOUN
eurjchem-1645	567	48	)	)	PUNCT
eurjchem-1645	567	49	,	,	PUNCT
eurjchem-1645	567	50	8.18‐8.02	8.18‐8.02	NUM
eurjchem-1645	567	51	(	(	PUNCT
eurjchem-1645	567	52	q	q	NOUN
eurjchem-1645	567	53	,	,	PUNCT
eurjchem-1645	567	54	2h	2h	NUM
eurjchem-1645	567	55	,	,	PUNCT
eurjchem-1645	567	56	ar‐h	ar‐h	NOUN
eurjchem-1645	567	57	)	)	PUNCT
eurjchem-1645	567	58	,	,	PUNCT
eurjchem-1645	567	59	8.6(s	8.6(s	NUM
eurjchem-1645	567	60	,	,	PUNCT
eurjchem-1645	567	61	1h	1h	NUM
eurjchem-1645	567	62	,	,	PUNCT
eurjchem-1645	567	63	ar‐h	ar‐h	NOUN
eurjchem-1645	567	64	)	)	PUNCT
eurjchem-1645	567	65	,	,	PUNCT
eurjchem-1645	567	66	8.83	8.83	NUM
eurjchem-1645	567	67	(	(	PUNCT
eurjchem-1645	567	68	d	d	NOUN
eurjchem-1645	567	69	,	,	PUNCT
eurjchem-1645	567	70	2h	2h	NUM
eurjchem-1645	567	71	,	,	PUNCT
eurjchem-1645	567	72	j	j	PROPN
eurjchem-1645	567	73	=	=	SYM
eurjchem-1645	567	74	hz	hz	PROPN
eurjchem-1645	567	75	,	,	PUNCT
eurjchem-1645	567	76	ar‐h	ar‐h	NOUN
eurjchem-1645	567	77	)	)	PUNCT
eurjchem-1645	567	78	,	,	PUNCT
eurjchem-1645	567	79	9.38	9.38	NUM
eurjchem-1645	567	80	(	(	PUNCT
eurjchem-1645	567	81	s	s	PROPN
eurjchem-1645	567	82	,	,	PUNCT
eurjchem-1645	567	83	1h	1h	NUM
eurjchem-1645	567	84	,	,	PUNCT
eurjchem-1645	567	85	ar‐h	ar‐h	NOUN
eurjchem-1645	567	86	)	)	PUNCT
eurjchem-1645	567	87	,	,	PUNCT
eurjchem-1645	567	88	14.1	14.1	NUM
eurjchem-1645	567	89	(	(	PUNCT
eurjchem-1645	567	90	br	br	NOUN
eurjchem-1645	567	91	.	.	PUNCT
eurjchem-1645	567	92	s	s	PART
eurjchem-1645	567	93	,	,	PUNCT
eurjchem-1645	567	94	1h	1h	NUM
eurjchem-1645	567	95	,	,	PUNCT
eurjchem-1645	567	96	nh	nh	PROPN
eurjchem-1645	567	97	)	)	PUNCT
eurjchem-1645	567	98	.	.	PUNCT
eurjchem-1645	568	1	13c	13c	NOUN
eurjchem-1645	568	2	nmr	nmr	NOUN
eurjchem-1645	568	3	(	(	PUNCT
eurjchem-1645	568	4	100	100	NUM
eurjchem-1645	568	5	mhz	mhz	NOUN
eurjchem-1645	568	6	,	,	PUNCT
eurjchem-1645	568	7	cdcl3	cdcl3	PROPN
eurjchem-1645	568	8	,	,	PUNCT
eurjchem-1645	568	9	δ	δ	PROPN
eurjchem-1645	568	10	,	,	PUNCT
eurjchem-1645	568	11	ppm	ppm	NOUN
eurjchem-1645	568	12	):	):	PUNCT
eurjchem-1645	568	13	12.53	12.53	NUM
eurjchem-1645	568	14	,	,	PUNCT
eurjchem-1645	568	15	44.57	44.57	NUM
eurjchem-1645	568	16	,	,	PUNCT
eurjchem-1645	568	17	69.36	69.36	NUM
eurjchem-1645	568	18	,	,	PUNCT
eurjchem-1645	568	19	110.31	110.31	NUM
eurjchem-1645	568	20	,	,	PUNCT
eurjchem-1645	568	21	116.12	116.12	NUM
eurjchem-1645	568	22	,	,	PUNCT
eurjchem-1645	568	23	127	127	NUM
eurjchem-1645	568	24	,	,	PUNCT
eurjchem-1645	568	25	127.11	127.11	NUM
eurjchem-1645	568	26	,	,	PUNCT
eurjchem-1645	568	27	128.45	128.45	NUM
eurjchem-1645	568	28	,	,	PUNCT
eurjchem-1645	568	29	128.85	128.85	NUM
eurjchem-1645	568	30	,	,	PUNCT
eurjchem-1645	568	31	129.11	129.11	NUM
eurjchem-1645	568	32	,	,	PUNCT
eurjchem-1645	568	33	129.34	129.34	NUM
eurjchem-1645	568	34	,	,	PUNCT
eurjchem-1645	568	35	130.17	130.17	NUM
eurjchem-1645	568	36	,	,	PUNCT
eurjchem-1645	568	37	132.23	132.23	NUM
eurjchem-1645	568	38	,	,	PUNCT
eurjchem-1645	568	39	134.68	134.68	NUM
eurjchem-1645	568	40	,	,	PUNCT
eurjchem-1645	568	41	157.88	157.88	NUM
eurjchem-1645	568	42	,	,	PUNCT
eurjchem-1645	568	43	158.12	158.12	NUM
eurjchem-1645	568	44	.	.	PUNCT
eurjchem-1645	569	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	569	2	(	(	PUNCT
eurjchem-1645	569	3	ei	ei	PROPN
eurjchem-1645	569	4	,	,	PUNCT
eurjchem-1645	569	5	m	m	PROPN
eurjchem-1645	569	6	/	/	SYM
eurjchem-1645	569	7	z	z	NOUN
eurjchem-1645	569	8	):	):	PUNCT
eurjchem-1645	569	9	343	343	NUM
eurjchem-1645	569	10	(	(	PUNCT
eurjchem-1645	569	11	m+h	m+h	PROPN
eurjchem-1645	569	12	)	)	PUNCT
eurjchem-1645	569	13	.	.	PUNCT
eurjchem-1645	570	1	anal	anal	PROPN
eurjchem-1645	570	2	.	.	PUNCT
eurjchem-1645	570	3	calcd	calcd	NOUN
eurjchem-1645	570	4	.	.	PUNCT
eurjchem-1645	571	1	for	for	ADP
eurjchem-1645	571	2	c19h14n6o	c19h14n6o	NOUN
eurjchem-1645	571	3	:	:	PUNCT
eurjchem-1645	571	4	c	c	X
eurjchem-1645	571	5	,	,	PUNCT
eurjchem-1645	571	6	66.66	66.66	NUM
eurjchem-1645	571	7	;	;	PUNCT
eurjchem-1645	571	8	h	h	NOUN
eurjchem-1645	571	9	,	,	PUNCT
eurjchem-1645	571	10	4.12	4.12	NUM
eurjchem-1645	571	11	;	;	PUNCT
eurjchem-1645	571	12	n	n	CCONJ
eurjchem-1645	571	13	,	,	PUNCT
eurjchem-1645	571	14	24.55	24.55	NUM
eurjchem-1645	571	15	.	.	PUNCT
eurjchem-1645	571	16	found	find	VERB
eurjchem-1645	571	17	:	:	PUNCT
eurjchem-1645	572	1	c	c	X
eurjchem-1645	572	2	,	,	PUNCT
eurjchem-1645	572	3	66.67	66.67	NUM
eurjchem-1645	572	4	;	;	PUNCT
eurjchem-1645	573	1	h	h	NOUN
eurjchem-1645	573	2	,	,	PUNCT
eurjchem-1645	573	3	4.10	4.10	NUM
eurjchem-1645	573	4	;	;	PUNCT
eurjchem-1645	573	5	n	n	CCONJ
eurjchem-1645	573	6	,	,	PUNCT
eurjchem-1645	573	7	24.57	24.57	NUM
eurjchem-1645	573	8	%	%	NOUN
eurjchem-1645	573	9	.	.	PUNCT
eurjchem-1645	574	1	hplc	hplc	NOUN
eurjchem-1645	574	2	:	:	PUNCT
eurjchem-1645	574	3	r.t	r.t	PROPN
eurjchem-1645	574	4	.	.	PUNCT
eurjchem-1645	575	1	=	=	PROPN
eurjchem-1645	575	2	8.42	8.42	NUM
eurjchem-1645	575	3	min	min	NOUN
eurjchem-1645	575	4	,	,	PUNCT
eurjchem-1645	575	5	purity	purity	NOUN
eurjchem-1645	575	6	=	=	NOUN
eurjchem-1645	575	7	98.0	98.0	NUM
eurjchem-1645	575	8	%	%	NOUN
eurjchem-1645	575	9	.	.	PUNCT
eurjchem-1645	576	1	5	5	NUM
eurjchem-1645	576	2	,	,	PUNCT
eurjchem-1645	576	3	6‐dihydro‐6‐(pyrimidin‐2‐yl)‐3‐(quinolin‐5‐yl)‐1h‐pyra	6‐dihydro‐6‐(pyrimidin‐2‐yl)‐3‐(quinolin‐5‐yl)‐1h‐pyra	NUM
eurjchem-1645	576	4	zolo[3,4‐c]pyridin‐7(4h)‐one	zolo[3,4‐c]pyridin‐7(4h)‐one	NOUN
eurjchem-1645	576	5	(	(	PUNCT
eurjchem-1645	576	6	15h	15h	NUM
eurjchem-1645	576	7	):	):	PUNCT
eurjchem-1645	576	8	color	color	NOUN
eurjchem-1645	576	9	:	:	PUNCT
eurjchem-1645	576	10	white	white	ADJ
eurjchem-1645	576	11	.	.	PUNCT
eurjchem-1645	577	1	yield	yield	NOUN
eurjchem-1645	577	2	:	:	PUNCT
eurjchem-1645	577	3	80	80	NUM
eurjchem-1645	577	4	%	%	NOUN
eurjchem-1645	577	5	.	.	PUNCT
eurjchem-1645	578	1	m.p	m.p	PROPN
eurjchem-1645	578	2	.	.	PROPN
eurjchem-1645	578	3	:	:	PUNCT
eurjchem-1645	579	1	209‐210	209‐210	PROPN
eurjchem-1645	579	2	°	°	PROPN
eurjchem-1645	579	3	c	c	PROPN
eurjchem-1645	579	4	.	.	PUNCT
eurjchem-1645	580	1	1h	1h	NUM
eurjchem-1645	580	2	nmr	nmr	NOUN
eurjchem-1645	580	3	(	(	PUNCT
eurjchem-1645	580	4	400	400	NUM
eurjchem-1645	580	5	mhz	mhz	NOUN
eurjchem-1645	580	6	,	,	PUNCT
eurjchem-1645	580	7	dmso‐d6	dmso‐d6	PROPN
eurjchem-1645	580	8	,	,	PUNCT
eurjchem-1645	580	9	δ	δ	PROPN
eurjchem-1645	580	10	,	,	PUNCT
eurjchem-1645	580	11	ppm	ppm	NUM
eurjchem-1645	580	12	):	):	PUNCT
eurjchem-1645	580	13	2.80	2.80	NUM
eurjchem-1645	580	14	(	(	PUNCT
eurjchem-1645	580	15	q	q	NOUN
eurjchem-1645	580	16	,	,	PUNCT
eurjchem-1645	580	17	2h	2h	NUM
eurjchem-1645	580	18	,	,	PUNCT
eurjchem-1645	580	19	ch2	ch2	PROPN
eurjchem-1645	580	20	)	)	PUNCT
eurjchem-1645	580	21	,	,	PUNCT
eurjchem-1645	580	22	4.20	4.20	NUM
eurjchem-1645	580	23	(	(	PUNCT
eurjchem-1645	580	24	q	q	NOUN
eurjchem-1645	580	25	,	,	PUNCT
eurjchem-1645	580	26	2h	2h	NUM
eurjchem-1645	580	27	,	,	PUNCT
eurjchem-1645	580	28	n‐ch2	n‐ch2	PROPN
eurjchem-1645	580	29	)	)	PUNCT
eurjchem-1645	580	30	,	,	PUNCT
eurjchem-1645	580	31	7.36	7.36	NUM
eurjchem-1645	580	32	(	(	PUNCT
eurjchem-1645	580	33	t	t	PROPN
eurjchem-1645	580	34	,	,	PUNCT
eurjchem-1645	580	35	1h	1h	NUM
eurjchem-1645	580	36	,	,	PUNCT
eurjchem-1645	580	37	j	j	PROPN
eurjchem-1645	580	38	=	=	SYM
eurjchem-1645	580	39	7.2	7.2	NUM
eurjchem-1645	580	40	hz	hz	NOUN
eurjchem-1645	580	41	,	,	PUNCT
eurjchem-1645	580	42	ar‐h	ar‐h	PROPN
eurjchem-1645	580	43	)	)	PUNCT
eurjchem-1645	580	44	,	,	PUNCT
eurjchem-1645	580	45	7.40	7.40	NUM
eurjchem-1645	580	46	(	(	PUNCT
eurjchem-1645	580	47	d	d	PROPN
eurjchem-1645	580	48	,	,	PUNCT
eurjchem-1645	580	49	1h	1h	NUM
eurjchem-1645	580	50	,	,	PUNCT
eurjchem-1645	580	51	j	j	PROPN
eurjchem-1645	580	52	=	=	SYM
eurjchem-1645	580	53	7.4	7.4	NUM
eurjchem-1645	580	54	hz	hz	VERB
eurjchem-1645	580	55	,	,	PUNCT
eurjchem-1645	580	56	ar‐h	ar‐h	NOUN
eurjchem-1645	580	57	)	)	PUNCT
eurjchem-1645	580	58	,	,	PUNCT
eurjchem-1645	580	59	7.64	7.64	NUM
eurjchem-1645	580	60	(	(	PUNCT
eurjchem-1645	580	61	d	d	PROPN
eurjchem-1645	580	62	,	,	PUNCT
eurjchem-1645	580	63	2h	2h	NUM
eurjchem-1645	580	64	,	,	PUNCT
eurjchem-1645	580	65	j	j	PROPN
eurjchem-1645	580	66	=	=	SYM
eurjchem-1645	580	67	8	8	NUM
eurjchem-1645	580	68	hz	hz	NOUN
eurjchem-1645	580	69	,	,	PUNCT
eurjchem-1645	580	70	ar‐h	ar‐h	NOUN
eurjchem-1645	580	71	)	)	PUNCT
eurjchem-1645	580	72	,	,	PUNCT
eurjchem-1645	580	73	7.81	7.81	NUM
eurjchem-1645	580	74	(	(	PUNCT
eurjchem-1645	580	75	t	t	PROPN
eurjchem-1645	580	76	,	,	PUNCT
eurjchem-1645	580	77	1h	1h	NUM
eurjchem-1645	580	78	,	,	PUNCT
eurjchem-1645	580	79	j	j	PROPN
eurjchem-1645	580	80	=	=	SYM
eurjchem-1645	580	81	7.6	7.6	NUM
eurjchem-1645	580	82	hz	hz	NOUN
eurjchem-1645	580	83	,	,	PUNCT
eurjchem-1645	580	84	ar‐h	ar‐h	PROPN
eurjchem-1645	580	85	)	)	PUNCT
eurjchem-1645	580	86	,	,	PUNCT
eurjchem-1645	580	87	8.12	8.12	NUM
eurjchem-1645	580	88	(	(	PUNCT
eurjchem-1645	580	89	d	d	PROPN
eurjchem-1645	580	90	,	,	PUNCT
eurjchem-1645	580	91	1h	1h	NUM
eurjchem-1645	580	92	,	,	PUNCT
eurjchem-1645	580	93	j	j	PROPN
eurjchem-1645	580	94	=	=	SYM
eurjchem-1645	580	95	7.4	7.4	NUM
eurjchem-1645	580	96	hz	hz	VERB
eurjchem-1645	580	97	,	,	PUNCT
eurjchem-1645	580	98	ar‐h	ar‐h	PROPN
eurjchem-1645	580	99	)	)	PUNCT
eurjchem-1645	580	100	,	,	PUNCT
eurjchem-1645	580	101	8.80	8.80	NUM
eurjchem-1645	580	102	(	(	PUNCT
eurjchem-1645	580	103	d	d	PROPN
eurjchem-1645	580	104	,	,	PUNCT
eurjchem-1645	580	105	2h	2h	NUM
eurjchem-1645	580	106	,	,	PUNCT
eurjchem-1645	580	107	j	j	PROPN
eurjchem-1645	580	108	=	=	SYM
eurjchem-1645	580	109	7.6	7.6	NUM
eurjchem-1645	580	110	hz	hz	NOUN
eurjchem-1645	580	111	,	,	PUNCT
eurjchem-1645	580	112	ar‐h	ar‐h	PROPN
eurjchem-1645	580	113	)	)	PUNCT
eurjchem-1645	580	114	,	,	PUNCT
eurjchem-1645	580	115	8.96	8.96	NUM
eurjchem-1645	580	116	(	(	PUNCT
eurjchem-1645	580	117	s	s	PROPN
eurjchem-1645	580	118	,	,	PUNCT
eurjchem-1645	580	119	1h	1h	NUM
eurjchem-1645	580	120	,	,	PUNCT
eurjchem-1645	580	121	ar‐h	ar‐h	NOUN
eurjchem-1645	580	122	)	)	PUNCT
eurjchem-1645	580	123	,	,	PUNCT
eurjchem-1645	580	124	13.98‐14.2	13.98‐14.2	NUM
eurjchem-1645	580	125	(	(	PUNCT
eurjchem-1645	580	126	br	br	NOUN
eurjchem-1645	580	127	.	.	PUNCT
eurjchem-1645	581	1	s	s	PART
eurjchem-1645	581	2	,	,	PUNCT
eurjchem-1645	581	3	1h	1h	NUM
eurjchem-1645	581	4	,	,	PUNCT
eurjchem-1645	581	5	nh	nh	PROPN
eurjchem-1645	581	6	)	)	PUNCT
eurjchem-1645	581	7	.	.	PUNCT
eurjchem-1645	582	1	13c	13c	NOUN
eurjchem-1645	582	2	nmr	nmr	NOUN
eurjchem-1645	582	3	(	(	PUNCT
eurjchem-1645	582	4	100	100	NUM
eurjchem-1645	582	5	mhz	mhz	NOUN
eurjchem-1645	582	6	,	,	PUNCT
eurjchem-1645	582	7	cdcl3	cdcl3	PROPN
eurjchem-1645	582	8	,	,	PUNCT
eurjchem-1645	582	9	δ	δ	PROPN
eurjchem-1645	582	10	,	,	PUNCT
eurjchem-1645	582	11	ppm	ppm	NOUN
eurjchem-1645	582	12	):	):	PUNCT
eurjchem-1645	582	13	15.35	15.35	NUM
eurjchem-1645	582	14	,	,	PUNCT
eurjchem-1645	582	15	45.33	45.33	NUM
eurjchem-1645	582	16	,	,	PUNCT
eurjchem-1645	582	17	110.20	110.20	NUM
eurjchem-1645	582	18	,	,	PUNCT
eurjchem-1645	582	19	116.78	116.78	NUM
eurjchem-1645	582	20	,	,	PUNCT
eurjchem-1645	582	21	119.47	119.47	NUM
eurjchem-1645	582	22	,	,	PUNCT
eurjchem-1645	582	23	121.20	121.20	NUM
eurjchem-1645	582	24	,	,	PUNCT
eurjchem-1645	582	25	125.38	125.38	NUM
eurjchem-1645	582	26	,	,	PUNCT
eurjchem-1645	582	27	127.29	127.29	NUM
eurjchem-1645	582	28	,	,	PUNCT
eurjchem-1645	582	29	129.31	129.31	NUM
eurjchem-1645	582	30	,	,	PUNCT
eurjchem-1645	582	31	130.00	130.00	NUM
eurjchem-1645	582	32	,	,	PUNCT
eurjchem-1645	582	33	130.12	130.12	NUM
eurjchem-1645	582	34	,	,	PUNCT
eurjchem-1645	582	35	136.46	136.46	NUM
eurjchem-1645	582	36	,	,	PUNCT
eurjchem-1645	582	37	137.12	137.12	NUM
eurjchem-1645	582	38	,	,	PUNCT
eurjchem-1645	582	39	147.45	147.45	NUM
eurjchem-1645	582	40	,	,	PUNCT
eurjchem-1645	582	41	150.51	150.51	NUM
eurjchem-1645	582	42	,	,	PUNCT
eurjchem-1645	582	43	156.60	156.60	NUM
eurjchem-1645	582	44	,	,	PUNCT
eurjchem-1645	582	45	159.12	159.12	NUM
eurjchem-1645	582	46	,	,	PUNCT
eurjchem-1645	582	47	162.84	162.84	NUM
eurjchem-1645	582	48	.	.	PUNCT
eurjchem-1645	583	1	lc‐ms	lc‐ms	PROPN
eurjchem-1645	583	2	(	(	PUNCT
eurjchem-1645	583	3	ei	ei	PROPN
eurjchem-1645	583	4	,	,	PUNCT
eurjchem-1645	583	5	m	m	PROPN
eurjchem-1645	583	6	/	/	SYM
eurjchem-1645	583	7	z	z	NOUN
eurjchem-1645	583	8	):	):	PUNCT
eurjchem-1645	583	9	343	343	NUM
eurjchem-1645	583	10	(	(	PUNCT
eurjchem-1645	583	11	m+h	m+h	PROPN
eurjchem-1645	583	12	)	)	PUNCT
eurjchem-1645	583	13	.	.	PUNCT
eurjchem-1645	584	1	anal	anal	PROPN
eurjchem-1645	584	2	.	.	PUNCT
eurjchem-1645	584	3	calcd	calcd	NOUN
eurjchem-1645	584	4	.	.	PUNCT
eurjchem-1645	585	1	for	for	SCONJ
eurjchem-1645	585	2	c19h14	c19h14	NOUN
eurjchem-1645	585	3	n6o	n6o	PROPN
eurjchem-1645	585	4	:	:	PUNCT
eurjchem-1645	585	5	c	c	X
eurjchem-1645	585	6	,	,	PUNCT
eurjchem-1645	585	7	66.66	66.66	NUM
eurjchem-1645	585	8	;	;	PUNCT
eurjchem-1645	585	9	h	h	NOUN
eurjchem-1645	585	10	,	,	PUNCT
eurjchem-1645	585	11	4.12	4.12	NUM
eurjchem-1645	585	12	;	;	PUNCT
eurjchem-1645	585	13	n	n	CCONJ
eurjchem-1645	585	14	,	,	PUNCT
eurjchem-1645	585	15	24.55	24.55	NUM
eurjchem-1645	585	16	.	.	PUNCT
eurjchem-1645	585	17	found	find	VERB
eurjchem-1645	585	18	:	:	PUNCT
eurjchem-1645	586	1	c	c	X
eurjchem-1645	586	2	,	,	PUNCT
eurjchem-1645	586	3	66.67	66.67	NUM
eurjchem-1645	586	4	;	;	PUNCT
eurjchem-1645	586	5	h	h	NOUN
eurjchem-1645	586	6	,	,	PUNCT
eurjchem-1645	586	7	4.11	4.11	NUM
eurjchem-1645	586	8	;	;	PUNCT
eurjchem-1645	586	9	n	n	CCONJ
eurjchem-1645	586	10	,	,	PUNCT
eurjchem-1645	586	11	24.54	24.54	NUM
eurjchem-1645	586	12	%	%	NOUN
eurjchem-1645	586	13	.	.	PUNCT
eurjchem-1645	587	1	hplc	hplc	NOUN
eurjchem-1645	587	2	:	:	PUNCT
eurjchem-1645	587	3	r.t	r.t	PROPN
eurjchem-1645	587	4	.	.	PUNCT
eurjchem-1645	588	1	=	=	NOUN
eurjchem-1645	588	2	6.37	6.37	NUM
eurjchem-1645	588	3	min	min	NOUN
eurjchem-1645	588	4	,	,	PUNCT
eurjchem-1645	588	5	purity	purity	NOUN
eurjchem-1645	588	6	=	=	SYM
eurjchem-1645	588	7	99.3	99.3	NUM
eurjchem-1645	588	8	%	%	NOUN
eurjchem-1645	588	9	.	.	PUNCT
eurjchem-1645	589	1	2.3	2.3	NUM
eurjchem-1645	589	2	.	.	PUNCT
eurjchem-1645	590	1	biological	biological	ADJ
eurjchem-1645	590	2	evaluation	evaluation	NOUN
eurjchem-1645	590	3	all	all	DET
eurjchem-1645	590	4	the	the	DET
eurjchem-1645	590	5	synthesized	synthesize	VERB
eurjchem-1645	590	6	compounds	compound	NOUN
eurjchem-1645	590	7	were	be	AUX
eurjchem-1645	590	8	tested	test	VERB
eurjchem-1645	590	9	for	for	ADP
eurjchem-1645	590	10	their	their	PRON
eurjchem-1645	590	11	in	in	ADP
eurjchem-1645	590	12	vitro	vitro	X
eurjchem-1645	590	13	anticancer	anticancer	NOUN
eurjchem-1645	590	14	activity	activity	NOUN
eurjchem-1645	590	15	against	against	ADP
eurjchem-1645	590	16	various	various	ADJ
eurjchem-1645	590	17	cancer	cancer	NOUN
eurjchem-1645	590	18	cell	cell	NOUN
eurjchem-1645	590	19	lines	line	NOUN
eurjchem-1645	590	20	.	.	PUNCT
eurjchem-1645	591	1	pawar	pawar	PROPN
eurjchem-1645	591	2	et	et	PROPN
eurjchem-1645	591	3	al	al	PROPN
eurjchem-1645	591	4	.	.	PUNCT
eurjchem-1645	591	5	/	/	SYM
eurjchem-1645	591	6	european	european	PROPN
eurjchem-1645	591	7	journal	journal	PROPN
eurjchem-1645	591	8	of	of	ADP
eurjchem-1645	591	9	chemistry	chemistry	NOUN
eurjchem-1645	591	10	8	8	NUM
eurjchem-1645	591	11	(	(	PUNCT
eurjchem-1645	591	12	4	4	NUM
eurjchem-1645	591	13	)	)	PUNCT
eurjchem-1645	591	14	(	(	PUNCT
eurjchem-1645	591	15	2017	2017	NUM
eurjchem-1645	591	16	)	)	PUNCT
eurjchem-1645	591	17	400‐409	400‐409	NUM
eurjchem-1645	591	18	407	407	NUM
eurjchem-1645	591	19	table	table	NOUN
eurjchem-1645	591	20	1	1	NUM
eurjchem-1645	591	21	.	.	PUNCT
eurjchem-1645	592	1	in	in	ADP
eurjchem-1645	592	2	vitro	vitro	X
eurjchem-1645	592	3	anticancer	anticancer	NOUN
eurjchem-1645	592	4	screening	screening	NOUN
eurjchem-1645	592	5	of	of	ADP
eurjchem-1645	592	6	the	the	DET
eurjchem-1645	592	7	synthesized	synthesize	VERB
eurjchem-1645	592	8	compounds	compound	NOUN
eurjchem-1645	592	9	against	against	ADP
eurjchem-1645	592	10	five	five	NUM
eurjchem-1645	592	11	cell	cell	NOUN
eurjchem-1645	592	12	lines	line	NOUN
eurjchem-1645	592	13	.	.	PUNCT
eurjchem-1645	593	1	compound	compound	VERB
eurjchem-1645	593	2	a‐549	a‐549	PRON
eurjchem-1645	594	1	a	a	DET
eurjchem-1645	594	2	si	si	X
eurjchem-1645	594	3	f	f	PROPN
eurjchem-1645	594	4	hela	hela	PROPN
eurjchem-1645	594	5	b	b	X
eurjchem-1645	594	6	si	si	PROPN
eurjchem-1645	594	7	f	f	X
eurjchem-1645	594	8	mcf‐7	mcf‐7	PROPN
eurjchem-1645	595	1	c	c	PROPN
eurjchem-1645	595	2	si	si	PROPN
eurjchem-1645	596	1	f	f	PROPN
eurjchem-1645	596	2	du‐145	du‐145	PROPN
eurjchem-1645	596	3	d	d	PROPN
eurjchem-1645	596	4	si	si	PROPN
eurjchem-1645	596	5	f	f	PROPN
eurjchem-1645	596	6	huvec	huvec	PROPN
eurjchem-1645	596	7	e	e	PROPN
eurjchem-1645	596	8	13a	13a	PROPN
eurjchem-1645	596	9	22.72±0.11	22.72±0.11	NUM
eurjchem-1645	596	10	4.04	4.04	NUM
eurjchem-1645	596	11	23.87±0.08	23.87±0.08	NUM
eurjchem-1645	596	12	3.84	3.84	NUM
eurjchem-1645	596	13	24.12±0.06	24.12±0.06	NUM
eurjchem-1645	596	14	3.80	3.80	NUM
eurjchem-1645	596	15	28.86±0.22	28.86±0.22	NUM
eurjchem-1645	596	16	3.18	3.18	NUM
eurjchem-1645	596	17	91.8±0.28	91.8±0.28	NUM
eurjchem-1645	596	18	13b	13b	NOUN
eurjchem-1645	596	19	15.81±0.11	15.81±0.11	NUM
eurjchem-1645	596	20	5.13	5.13	NUM
eurjchem-1645	596	21	14.32±0.04	14.32±0.04	NUM
eurjchem-1645	596	22	6.74	6.74	NUM
eurjchem-1645	596	23	26.32±0.06	26.32±0.06	NUM
eurjchem-1645	596	24	3.67	3.67	NUM
eurjchem-1645	596	25	33.73±0.12	33.73±0.12	NUM
eurjchem-1645	596	26	2.86	2.86	NUM
eurjchem-1645	596	27	96.6±0.14	96.6±0.14	NUM
eurjchem-1645	596	28	13c	13c	NOUN
eurjchem-1645	596	29	6.81±0.11	6.81±0.11	NUM
eurjchem-1645	596	30	12.73	12.73	NUM
eurjchem-1645	596	31	11.32±0.04	11.32±0.04	NUM
eurjchem-1645	596	32	7.65	7.65	NUM
eurjchem-1645	596	33	17.32±0.06	17.32±0.06	NUM
eurjchem-1645	596	34	5.00	5.00	NUM
eurjchem-1645	596	35	10.73±0.12	10.73±0.12	NUM
eurjchem-1645	596	36	8.07	8.07	NUM
eurjchem-1645	596	37	86.6±0.28	86.6±0.28	NUM
eurjchem-1645	596	38	13d	13d	NOUN
eurjchem-1645	596	39	10.65±0.11	10.65±0.11	NUM
eurjchem-1645	596	40	8.41	8.41	NUM
eurjchem-1645	596	41	18.79±0.22	18.79±0.22	NUM
eurjchem-1645	596	42	4.76	4.76	NUM
eurjchem-1645	596	43	16.86±0.12	16.86±0.12	NUM
eurjchem-1645	596	44	5.31	5.31	NUM
eurjchem-1645	596	45	20.82±0.11	20.82±0.11	NUM
eurjchem-1645	596	46	4.30	4.30	NUM
eurjchem-1645	596	47	89.6±0.28	89.6±0.28	NUM
eurjchem-1645	596	48	13e	13e	NOUN
eurjchem-1645	596	49	13.86±0.08	13.86±0.08	NUM
eurjchem-1645	596	50	6.39	6.39	NUM
eurjchem-1645	596	51	24.38±0.06	24.38±0.06	NUM
eurjchem-1645	596	52	3.63	3.63	NUM
eurjchem-1645	596	53	13.63±0.12	13.63±0.12	NUM
eurjchem-1645	596	54	6.50	6.50	NUM
eurjchem-1645	596	55	11.52±0.22	11.52±0.22	NUM
eurjchem-1645	596	56	7.69	7.69	NUM
eurjchem-1645	596	57	88.7±0.12	88.7±0.12	NUM
eurjchem-1645	596	58	13f	13f	NOUN
eurjchem-1645	596	59	15.72±0.11	15.72±0.11	NUM
eurjchem-1645	596	60	6.08	6.08	NUM
eurjchem-1645	596	61	26.87±0.08	26.87±0.08	NUM
eurjchem-1645	596	62	3.55	3.55	NUM
eurjchem-1645	596	63	24.12±0.06	24.12±0.06	NUM
eurjchem-1645	596	64	3.96	3.96	NUM
eurjchem-1645	596	65	38.86±0.22	38.86±0.22	NUM
eurjchem-1645	596	66	2.46	2.46	NUM
eurjchem-1645	596	67	95.6±0.28	95.6±0.28	NUM
eurjchem-1645	596	68	13	13	NUM
eurjchem-1645	596	69	g	g	NOUN
eurjchem-1645	596	70	5.12±0.11	5.12±0.11	NUM
eurjchem-1645	596	71	17.42	17.42	NUM
eurjchem-1645	596	72	9.12±0.22	9.12±0.22	NOUN
eurjchem-1645	596	73	9.78	9.78	NUM
eurjchem-1645	596	74	9.36±0.12	9.36±0.12	NUM
eurjchem-1645	596	75	9.52	9.52	NUM
eurjchem-1645	596	76	13.52±0.11	13.52±0.11	NUM
eurjchem-1645	596	77	6.59	6.59	NUM
eurjchem-1645	596	78	89.2±0.28	89.2±0.28	NUM
eurjchem-1645	596	79	13h	13h	NOUN
eurjchem-1645	596	80	13.25±0.14	13.25±0.14	NUM
eurjchem-1645	596	81	6.53	6.53	NUM
eurjchem-1645	596	82	17.78±0.08	17.78±0.08	NUM
eurjchem-1645	596	83	4.87	4.87	NUM
eurjchem-1645	596	84	13.82±0.08	13.82±0.08	NUM
eurjchem-1645	596	85	6.26	6.26	NUM
eurjchem-1645	596	86	11.72±0.06	11.72±0.06	NUM
eurjchem-1645	596	87	7.38	7.38	NUM
eurjchem-1645	596	88	86.6±0.19	86.6±0.19	NUM
eurjchem-1645	596	89	15a	15a	NOUN
eurjchem-1645	596	90	10.82±0.11	10.82±0.11	NUM
eurjchem-1645	596	91	8.69	8.69	NUM
eurjchem-1645	596	92	13.39±0.22	13.39±0.22	NUM
eurjchem-1645	596	93	7.02	7.02	NUM
eurjchem-1645	596	94	11.36±0.12	11.36±0.12	NUM
eurjchem-1645	596	95	8.28	8.28	NUM
eurjchem-1645	596	96	9.52±0.11	9.52±0.11	NUM
eurjchem-1645	596	97	9.88	9.88	NUM
eurjchem-1645	596	98	94.1±0.26	94.1±0.26	NUM
eurjchem-1645	596	99	15b	15b	NOUN
eurjchem-1645	596	100	14.13±0.12	14.13±0.12	NUM
eurjchem-1645	596	101	6.18	6.18	NUM
eurjchem-1645	596	102	15.16±0.08	15.16±0.08	NUM
eurjchem-1645	596	103	5.76	5.76	NUM
eurjchem-1645	596	104	16.12±0.12	16.12±0.12	NUM
eurjchem-1645	596	105	5.42	5.42	NUM
eurjchem-1645	596	106	11.62±0.11	11.62±0.11	NUM
eurjchem-1645	596	107	7.52	7.52	NUM
eurjchem-1645	596	108	87.4±0.22	87.4±0.22	NUM
eurjchem-1645	596	109	15c	15c	NOUN
eurjchem-1645	596	110	23.86±0.08	23.86±0.08	NUM
eurjchem-1645	596	111	3.24	3.24	NUM
eurjchem-1645	596	112	14.38±0.06	14.38±0.06	NUM
eurjchem-1645	596	113	6.50	6.50	NUM
eurjchem-1645	596	114	20.63±0.12	20.63±0.12	NUM
eurjchem-1645	596	115	4.53	4.53	NUM
eurjchem-1645	596	116	11.52±0.22	11.52±0.22	NUM
eurjchem-1645	596	117	8.12	8.12	NUM
eurjchem-1645	596	118	93.6±0.12	93.6±0.12	NUM
eurjchem-1645	596	119	15d	15d	NUM
eurjchem-1645	596	120	11.72±0.11	11.72±0.11	NUM
eurjchem-1645	596	121	7.81	7.81	NUM
eurjchem-1645	596	122	8.87±0.08	8.87±0.08	PROPN
eurjchem-1645	596	123	10.32	10.32	NUM
eurjchem-1645	596	124	13.12±0.06	13.12±0.06	NUM
eurjchem-1645	596	125	6.98	6.98	NUM
eurjchem-1645	596	126	18.86±0.22	18.86±0.22	NUM
eurjchem-1645	596	127	4.85	4.85	NUM
eurjchem-1645	596	128	91.6±0.28	91.6±0.28	NUM
eurjchem-1645	596	129	15e	15e	NOUN
eurjchem-1645	596	130	23.82±0.11	23.82±0.11	NUM
eurjchem-1645	596	131	3.55	3.55	NUM
eurjchem-1645	596	132	20.99±0.22	20.99±0.22	NUM
eurjchem-1645	596	133	4.03	4.03	NUM
eurjchem-1645	596	134	19.36±0.12	19.36±0.12	NUM
eurjchem-1645	596	135	4.36	4.36	NUM
eurjchem-1645	596	136	12.52±0.11	12.52±0.11	NUM
eurjchem-1645	596	137	6.75	6.75	NUM
eurjchem-1645	596	138	84.6±0.28	84.6±0.28	NUM
eurjchem-1645	596	139	15f	15f	NOUN
eurjchem-1645	596	140	10.78±0.14	10.78±0.14	NUM
eurjchem-1645	596	141	8.12	8.12	NUM
eurjchem-1645	596	142	18.78±0.08	18.78±0.08	NUM
eurjchem-1645	596	143	4.66	4.66	NUM
eurjchem-1645	596	144	14.82±0.08	14.82±0.08	NUM
eurjchem-1645	596	145	5.91	5.91	NUM
eurjchem-1645	596	146	18.72±0.06	18.72±0.06	NUM
eurjchem-1645	596	147	4.67	4.67	NUM
eurjchem-1645	596	148	87.6±0.19	87.6±0.19	NUM
eurjchem-1645	596	149	15	15	NUM
eurjchem-1645	596	150	g	g	PROPN
eurjchem-1645	596	151	10.82±0.11	10.82±0.11	NUM
eurjchem-1645	596	152	8.78	8.78	NUM
eurjchem-1645	596	153	8.59±0.22	8.59±0.22	NOUN
eurjchem-1645	596	154	11.07	11.07	NUM
eurjchem-1645	596	155	8.36±0.12	8.36±0.12	NUM
eurjchem-1645	596	156	11.37	11.37	NUM
eurjchem-1645	596	157	17.52±0.11	17.52±0.11	NUM
eurjchem-1645	596	158	5.42	5.42	NUM
eurjchem-1645	596	159	95.1±0.26	95.1±0.26	NUM
eurjchem-1645	596	160	15h	15h	NUM
eurjchem-1645	596	161	9.13±0.12	9.13±0.12	NUM
eurjchem-1645	596	162	9.81	9.81	NUM
eurjchem-1645	596	163	14.16±0.08	14.16±0.08	NUM
eurjchem-1645	596	164	6.32	6.32	NUM
eurjchem-1645	596	165	6.12±0.12	6.12±0.12	NUM
eurjchem-1645	596	166	14.17	14.17	NUM
eurjchem-1645	596	167	11.62±0.11	11.62±0.11	NUM
eurjchem-1645	596	168	7.71	7.71	NUM
eurjchem-1645	596	169	89.6±0.22	89.6±0.22	NUM
eurjchem-1645	596	170	doxil	doxil	NOUN
eurjchem-1645	596	171	1.71±0.11	1.71±0.11	NUM
eurjchem-1645	596	172	51.57	51.57	NUM
eurjchem-1645	596	173	1.82±0.13	1.82±0.13	NUM
eurjchem-1645	597	1	48.46	48.46	NUM
eurjchem-1645	597	2	1.91±0.08	1.91±0.08	NUM
eurjchem-1645	597	3	46.17	46.17	NUM
eurjchem-1645	597	4	1.62±0.08	1.62±0.08	NUM
eurjchem-1645	597	5	54.44	54.44	NUM
eurjchem-1645	597	6	88.2±0.18	88.2±0.18	NUM
eurjchem-1645	597	7	a	a	DET
eurjchem-1645	597	8	a‐549	a‐549	NOUN
eurjchem-1645	597	9	:	:	PUNCT
eurjchem-1645	597	10	human	human	ADJ
eurjchem-1645	597	11	lung	lung	NOUN
eurjchem-1645	597	12	cancer	cancer	NOUN
eurjchem-1645	597	13	cell	cell	NOUN
eurjchem-1645	597	14	line	line	NOUN
eurjchem-1645	597	15	.	.	PUNCT
eurjchem-1645	598	1	b	b	X
eurjchem-1645	598	2	hela	hela	ADJ
eurjchem-1645	598	3	:	:	PUNCT
eurjchem-1645	598	4	human	human	ADJ
eurjchem-1645	598	5	cervical	cervical	ADJ
eurjchem-1645	598	6	cancer	cancer	NOUN
eurjchem-1645	598	7	cell	cell	NOUN
eurjchem-1645	598	8	line	line	NOUN
eurjchem-1645	598	9	(	(	PUNCT
eurjchem-1645	598	10	atcc	atcc	ADJ
eurjchem-1645	598	11	ccl‐2	ccl‐2	PROPN
eurjchem-1645	598	12	)	)	PUNCT
eurjchem-1645	598	13	.	.	PUNCT
eurjchem-1645	599	1	c	c	PROPN
eurjchem-1645	600	1	mcf‐7	mcf‐7	NOUN
eurjchem-1645	600	2	:	:	PUNCT
eurjchem-1645	600	3	human	human	ADJ
eurjchem-1645	600	4	breast	breast	NOUN
eurjchem-1645	600	5	cancer	cancer	NOUN
eurjchem-1645	600	6	cell	cell	NOUN
eurjchem-1645	600	7	line	line	NOUN
eurjchem-1645	600	8	.	.	PUNCT
eurjchem-1645	601	1	d	d	X
eurjchem-1645	601	2	du‐145	du‐145	NOUN
eurjchem-1645	601	3	:	:	PUNCT
eurjchem-1645	601	4	human	human	ADJ
eurjchem-1645	601	5	prostate	prostate	NOUN
eurjchem-1645	601	6	cancer	cancer	NOUN
eurjchem-1645	601	7	cell	cell	NOUN
eurjchem-1645	601	8	line	line	NOUN
eurjchem-1645	601	9	.	.	PUNCT
eurjchem-1645	602	1	e	e	NOUN
eurjchem-1645	602	2	huvec	huvec	NOUN
eurjchem-1645	602	3	:	:	PUNCT
eurjchem-1645	602	4	human	human	ADJ
eurjchem-1645	602	5	umbilical	umbilical	ADJ
eurjchem-1645	602	6	vein	vein	ADJ
eurjchem-1645	602	7	endothelial	endothelial	ADJ
eurjchem-1645	602	8	cell	cell	NOUN
eurjchem-1645	602	9	line	line	NOUN
eurjchem-1645	602	10	(	(	PUNCT
eurjchem-1645	602	11	atcc	atcc	PROPN
eurjchem-1645	602	12	crl‐1730	crl‐1730	PROPN
eurjchem-1645	602	13	)	)	PUNCT
eurjchem-1645	602	14	.	.	PUNCT
eurjchem-1645	603	1	f	f	PROPN
eurjchem-1645	603	2	selectivity	selectivity	NOUN
eurjchem-1645	603	3	index	index	NOUN
eurjchem-1645	603	4	(	(	PUNCT
eurjchem-1645	603	5	si	si	NOUN
eurjchem-1645	603	6	)	)	PUNCT
eurjchem-1645	603	7	=	=	SYM
eurjchem-1645	603	8	ic50	ic50	PROPN
eurjchem-1645	603	9	of	of	ADP
eurjchem-1645	603	10	pure	pure	ADJ
eurjchem-1645	603	11	compound	compound	NOUN
eurjchem-1645	603	12	in	in	ADP
eurjchem-1645	603	13	normal	normal	ADJ
eurjchem-1645	603	14	cell	cell	NOUN
eurjchem-1645	603	15	line	line	NOUN
eurjchem-1645	603	16	/	/	SYM
eurjchem-1645	603	17	ic50	ic50	PROPN
eurjchem-1645	603	18	of	of	ADP
eurjchem-1645	603	19	same	same	ADJ
eurjchem-1645	603	20	compound	compound	NOUN
eurjchem-1645	603	21	in	in	ADP
eurjchem-1645	603	22	cancer	cancer	NOUN
eurjchem-1645	603	23	cell	cell	NOUN
eurjchem-1645	603	24	line	line	NOUN
eurjchem-1645	603	25	.	.	PUNCT
eurjchem-1645	604	1	ic50	ic50	PROPN
eurjchem-1645	604	2	‐	‐	VERB
eurjchem-1645	604	3	the	the	DET
eurjchem-1645	604	4	concentration	concentration	NOUN
eurjchem-1645	604	5	required	require	VERB
eurjchem-1645	604	6	to	to	PART
eurjchem-1645	604	7	inhibit	inhibit	VERB
eurjchem-1645	604	8	50	50	NUM
eurjchem-1645	604	9	%	%	NOUN
eurjchem-1645	604	10	of	of	ADP
eurjchem-1645	604	11	cell	cell	NOUN
eurjchem-1645	604	12	population	population	NOUN
eurjchem-1645	604	13	.	.	PUNCT
eurjchem-1645	605	1	the	the	DET
eurjchem-1645	605	2	anticancer	anticancer	NOUN
eurjchem-1645	605	3	activity	activity	NOUN
eurjchem-1645	605	4	test	test	NOUN
eurjchem-1645	605	5	is	be	AUX
eurjchem-1645	605	6	performed	perform	VERB
eurjchem-1645	605	7	according	accord	VERB
eurjchem-1645	605	8	to	to	ADP
eurjchem-1645	605	9	the	the	DET
eurjchem-1645	605	10	proce‐dure	proce‐dure	NOUN
eurjchem-1645	605	11	developed	develop	VERB
eurjchem-1645	605	12	by	by	ADP
eurjchem-1645	605	13	the	the	DET
eurjchem-1645	605	14	national	national	PROPN
eurjchem-1645	605	15	cancer	cancer	PROPN
eurjchem-1645	605	16	institute	institute	PROPN
eurjchem-1645	605	17	(	(	PUNCT
eurjchem-1645	605	18	nci	nci	PROPN
eurjchem-1645	605	19	,	,	PUNCT
eurjchem-1645	605	20	usa	usa	PROPN
eurjchem-1645	605	21	)	)	PUNCT
eurjchem-1645	605	22	in	in	ADP
eurjchem-1645	605	23	the	the	DET
eurjchem-1645	605	24	‘	'	PUNCT
eurjchem-1645	605	25	in	in	X
eurjchem-1645	605	26	vitro	vitro	X
eurjchem-1645	605	27	anticancer	anticancer	NOUN
eurjchem-1645	605	28	drug	drug	NOUN
eurjchem-1645	605	29	discovery	discovery	PROPN
eurjchem-1645	605	30	screen	screen	NOUN
eurjchem-1645	605	31	’	'	PUNCT
eurjchem-1645	605	32	that	that	PRON
eurjchem-1645	605	33	uses	use	VERB
eurjchem-1645	605	34	the	the	DET
eurjchem-1645	605	35	protein‐binding	protein‐binde	VERB
eurjchem-1645	605	36	dye	dye	NOUN
eurjchem-1645	605	37	sulforhodamine	sulforhodamine	NOUN
eurjchem-1645	605	38	b	b	PROPN
eurjchem-1645	605	39	(	(	PUNCT
eurjchem-1645	605	40	srb	srb	PROPN
eurjchem-1645	605	41	)	)	PUNCT
eurjchem-1645	605	42	to	to	PART
eurjchem-1645	605	43	assess	assess	VERB
eurjchem-1645	605	44	cell	cell	NOUN
eurjchem-1645	605	45	growth	growth	NOUN
eurjchem-1645	606	1	[	[	X
eurjchem-1645	606	2	14,15	14,15	NUM
eurjchem-1645	606	3	]	]	PUNCT
eurjchem-1645	606	4	.	.	PUNCT
eurjchem-1645	607	1	briefly	briefly	NOUN
eurjchem-1645	607	2	,	,	PUNCT
eurjchem-1645	607	3	cells	cell	NOUN
eurjchem-1645	607	4	are	be	AUX
eurjchem-1645	607	5	grown	grow	VERB
eurjchem-1645	607	6	in	in	ADP
eurjchem-1645	607	7	96‐well	96‐well	NUM
eurjchem-1645	607	8	plates	plate	NOUN
eurjchem-1645	607	9	in	in	ADP
eurjchem-1645	607	10	suspension	suspension	NOUN
eurjchem-1645	607	11	and	and	CCONJ
eurjchem-1645	607	12	then	then	ADV
eurjchem-1645	607	13	exposed	expose	VERB
eurjchem-1645	607	14	for	for	ADP
eurjchem-1645	607	15	48	48	NUM
eurjchem-1645	607	16	hours	hour	NOUN
eurjchem-1645	607	17	to	to	ADP
eurjchem-1645	607	18	four	four	NUM
eurjchem-1645	607	19	serial	serial	ADJ
eurjchem-1645	607	20	concentrations	concentration	NOUN
eurjchem-1645	607	21	of	of	ADP
eurjchem-1645	607	22	1×10‐7	1×10‐7	NUM
eurjchem-1645	607	23	,	,	PUNCT
eurjchem-1645	607	24	1×10‐6	1×10‐6	NUM
eurjchem-1645	607	25	,	,	PUNCT
eurjchem-1645	607	26	1×10‐5	1×10‐5	NUM
eurjchem-1645	607	27	,	,	PUNCT
eurjchem-1645	607	28	1×10‐4	1×10‐4	NUM
eurjchem-1645	607	29	and	and	CCONJ
eurjchem-1645	607	30	1×10‐3	1×10‐3	NUM
eurjchem-1645	607	31	m	m	NOUN
eurjchem-1645	607	32	of	of	ADP
eurjchem-1645	607	33	each	each	DET
eurjchem-1645	607	34	compound	compound	NOUN
eurjchem-1645	607	35	.	.	PUNCT
eurjchem-1645	608	1	cells	cell	NOUN
eurjchem-1645	608	2	were	be	AUX
eurjchem-1645	608	3	fixed	fix	VERB
eurjchem-1645	608	4	and	and	CCONJ
eurjchem-1645	608	5	stained	stain	VERB
eurjchem-1645	608	6	with	with	ADP
eurjchem-1645	608	7	protein	protein	NOUN
eurjchem-1645	608	8	binding	bind	VERB
eurjchem-1645	608	9	srb	srb	PROPN
eurjchem-1645	608	10	stain	stain	NOUN
eurjchem-1645	608	11	.	.	PUNCT
eurjchem-1645	609	1	excess	excess	ADJ
eurjchem-1645	609	2	stain	stain	NOUN
eurjchem-1645	609	3	is	be	AUX
eurjchem-1645	609	4	washed	wash	VERB
eurjchem-1645	609	5	and	and	CCONJ
eurjchem-1645	609	6	bound	bind	VERB
eurjchem-1645	609	7	stain	stain	NOUN
eurjchem-1645	609	8	was	be	AUX
eurjchem-1645	609	9	solubilized	solubilize	VERB
eurjchem-1645	609	10	,	,	PUNCT
eurjchem-1645	609	11	and	and	CCONJ
eurjchem-1645	609	12	the	the	DET
eurjchem-1645	609	13	absorbance	absorbance	NOUN
eurjchem-1645	609	14	was	be	AUX
eurjchem-1645	609	15	measured	measure	VERB
eurjchem-1645	609	16	at	at	ADP
eurjchem-1645	609	17	492	492	NUM
eurjchem-1645	609	18	nm	nm	NOUN
eurjchem-1645	609	19	in	in	ADP
eurjchem-1645	609	20	a	a	DET
eurjchem-1645	609	21	plate	plate	NOUN
eurjchem-1645	609	22	reader	reader	NOUN
eurjchem-1645	609	23	.	.	PUNCT
eurjchem-1645	610	1	concentration	concentration	NOUN
eurjchem-1645	610	2	of	of	ADP
eurjchem-1645	610	3	the	the	DET
eurjchem-1645	610	4	compounds	compound	NOUN
eurjchem-1645	610	5	that	that	PRON
eurjchem-1645	610	6	inhibited	inhibit	VERB
eurjchem-1645	610	7	50	50	NUM
eurjchem-1645	610	8	%	%	NOUN
eurjchem-1645	610	9	of	of	ADP
eurjchem-1645	610	10	the	the	DET
eurjchem-1645	610	11	net	net	ADJ
eurjchem-1645	610	12	cell	cell	NOUN
eurjchem-1645	610	13	growth	growth	NOUN
eurjchem-1645	610	14	,	,	PUNCT
eurjchem-1645	610	15	growth	growth	NOUN
eurjchem-1645	610	16	inhibition	inhibition	NOUN
eurjchem-1645	610	17	of	of	ADP
eurjchem-1645	610	18	50	50	NUM
eurjchem-1645	610	19	%	%	NOUN
eurjchem-1645	610	20	(	(	PUNCT
eurjchem-1645	610	21	gi50	gi50	PROPN
eurjchem-1645	610	22	)	)	PUNCT
eurjchem-1645	610	23	,	,	PUNCT
eurjchem-1645	610	24	was	be	AUX
eurjchem-1645	610	25	calculated	calculate	VERB
eurjchem-1645	610	26	from	from	ADP
eurjchem-1645	610	27	the	the	DET
eurjchem-1645	610	28	dose	dose	NOUN
eurjchem-1645	610	29	response	response	NOUN
eurjchem-1645	610	30	curve	curve	NOUN
eurjchem-1645	610	31	obtained	obtain	VERB
eurjchem-1645	610	32	for	for	ADP
eurjchem-1645	610	33	each	each	DET
eurjchem-1645	610	34	test	test	NOUN
eurjchem-1645	610	35	compound	compound	NOUN
eurjchem-1645	610	36	and	and	CCONJ
eurjchem-1645	610	37	cell	cell	NOUN
eurjchem-1645	610	38	line	line	NOUN
eurjchem-1645	610	39	.	.	PUNCT
eurjchem-1645	611	1	gi50	gi50	PROPN
eurjchem-1645	611	2	values	value	NOUN
eurjchem-1645	611	3	were	be	AUX
eurjchem-1645	611	4	presen‐	presen‐	NOUN
eurjchem-1645	611	5	ted	te	VERB
eurjchem-1645	611	6	in	in	ADP
eurjchem-1645	611	7	micro	micro	PROPN
eurjchem-1645	611	8	molar	molar	NOUN
eurjchem-1645	611	9	(	(	PUNCT
eurjchem-1645	611	10	μm	μm	NUM
eurjchem-1645	611	11	)	)	PUNCT
eurjchem-1645	611	12	concentration	concentration	NOUN
eurjchem-1645	611	13	.	.	PUNCT
eurjchem-1645	612	1	doxorubicin	doxorubicin	PROPN
eurjchem-1645	612	2	was	be	AUX
eurjchem-1645	612	3	used	use	VERB
eurjchem-1645	612	4	as	as	ADP
eurjchem-1645	612	5	positive	positive	ADJ
eurjchem-1645	612	6	control	control	NOUN
eurjchem-1645	612	7	for	for	ADP
eurjchem-1645	612	8	the	the	DET
eurjchem-1645	612	9	comparison	comparison	NOUN
eurjchem-1645	612	10	of	of	ADP
eurjchem-1645	612	11	cytotoxicity	cytotoxicity	NOUN
eurjchem-1645	612	12	of	of	ADP
eurjchem-1645	612	13	synthesized	synthesize	VERB
eurjchem-1645	612	14	compounds	compound	NOUN
eurjchem-1645	612	15	.	.	PUNCT
eurjchem-1645	613	1	assays	assay	NOUN
eurjchem-1645	613	2	were	be	AUX
eurjchem-1645	613	3	performed	perform	VERB
eurjchem-1645	613	4	in	in	ADP
eurjchem-1645	613	5	triplicate	triplicate	NOUN
eurjchem-1645	613	6	on	on	ADP
eurjchem-1645	613	7	three	three	NUM
eurjchem-1645	613	8	independent	independent	ADJ
eurjchem-1645	613	9	experiments	experiment	NOUN
eurjchem-1645	613	10	and	and	CCONJ
eurjchem-1645	613	11	their	their	PRON
eurjchem-1645	613	12	mean	mean	ADJ
eurjchem-1645	613	13	values	value	NOUN
eurjchem-1645	613	14	are	be	AUX
eurjchem-1645	613	15	taken	take	VERB
eurjchem-1645	613	16	as	as	ADP
eurjchem-1645	613	17	a	a	DET
eurjchem-1645	613	18	final	final	ADJ
eurjchem-1645	613	19	reading	reading	NOUN
eurjchem-1645	613	20	.	.	PUNCT
eurjchem-1645	614	1	the	the	DET
eurjchem-1645	614	2	result	result	NOUN
eurjchem-1645	614	3	of	of	ADP
eurjchem-1645	614	4	this	this	DET
eurjchem-1645	614	5	study	study	NOUN
eurjchem-1645	614	6	indicates	indicate	VERB
eurjchem-1645	614	7	that	that	SCONJ
eurjchem-1645	614	8	compound	compound	NOUN
eurjchem-1645	614	9	13c	13c	NOUN
eurjchem-1645	614	10	,	,	PUNCT
eurjchem-1645	614	11	13	13	NUM
eurjchem-1645	614	12	g	g	NOUN
eurjchem-1645	614	13	,	,	PUNCT
eurjchem-1645	614	14	15	15	NUM
eurjchem-1645	614	15	g	g	NOUN
eurjchem-1645	614	16	and	and	CCONJ
eurjchem-1645	614	17	15h	15h	NUM
eurjchem-1645	614	18	shows	show	VERB
eurjchem-1645	614	19	prominent	prominent	ADJ
eurjchem-1645	614	20	anti‐	anti‐	PROPN
eurjchem-1645	614	21	cancer	cancer	NOUN
eurjchem-1645	614	22	activity	activity	NOUN
eurjchem-1645	614	23	in	in	ADP
eurjchem-1645	614	24	all	all	DET
eurjchem-1645	614	25	cell	cell	NOUN
eurjchem-1645	614	26	lines	line	NOUN
eurjchem-1645	614	27	,	,	PUNCT
eurjchem-1645	614	28	having	have	VERB
eurjchem-1645	614	29	growth	growth	NOUN
eurjchem-1645	614	30	inhibition	inhibition	NOUN
eurjchem-1645	614	31	of	of	ADP
eurjchem-1645	614	32	50	50	NUM
eurjchem-1645	614	33	(	(	PUNCT
eurjchem-1645	614	34	gi50	gi50	PROPN
eurjchem-1645	614	35	)	)	PUNCT
eurjchem-1645	614	36	values	value	NOUN
eurjchem-1645	614	37	of	of	ADP
eurjchem-1645	614	38	5.12	5.12	NUM
eurjchem-1645	614	39	to	to	ADP
eurjchem-1645	614	40	17.52	17.52	NUM
eurjchem-1645	614	41	µm	µm	NOUN
eurjchem-1645	614	42	(	(	PUNCT
eurjchem-1645	614	43	table	table	NOUN
eurjchem-1645	614	44	1	1	NUM
eurjchem-1645	614	45	)	)	PUNCT
eurjchem-1645	614	46	.	.	PUNCT
eurjchem-1645	615	1	all	all	DET
eurjchem-1645	615	2	experiments	experiment	NOUN
eurjchem-1645	615	3	were	be	AUX
eurjchem-1645	615	4	performed	perform	VERB
eurjchem-1645	615	5	in	in	ADP
eurjchem-1645	615	6	duplicate	duplicate	NOUN
eurjchem-1645	615	7	and	and	CCONJ
eurjchem-1645	615	8	repeated	repeat	VERB
eurjchem-1645	615	9	three	three	NUM
eurjchem-1645	615	10	times	time	NOUN
eurjchem-1645	615	11	.	.	PUNCT
eurjchem-1645	616	1	3	3	X
eurjchem-1645	616	2	.	.	NOUN
eurjchem-1645	616	3	results	result	NOUN
eurjchem-1645	616	4	and	and	CCONJ
eurjchem-1645	616	5	discussion	discussion	NOUN
eurjchem-1645	616	6	3.1	3.1	NUM
eurjchem-1645	616	7	.	.	PUNCT
eurjchem-1645	617	1	chemistry	chemistry	NOUN
eurjchem-1645	617	2	in	in	ADP
eurjchem-1645	617	3	scheme	scheme	NOUN
eurjchem-1645	617	4	1	1	NUM
eurjchem-1645	617	5	,	,	PUNCT
eurjchem-1645	617	6	step	step	NOUN
eurjchem-1645	617	7	(	(	PUNCT
eurjchem-1645	617	8	a	a	X
eurjchem-1645	617	9	)	)	PUNCT
eurjchem-1645	617	10	is	be	AUX
eurjchem-1645	617	11	enamine	enamine	VERB
eurjchem-1645	617	12	formation	formation	NOUN
eurjchem-1645	617	13	which	which	PRON
eurjchem-1645	617	14	is	be	AUX
eurjchem-1645	617	15	done	do	VERB
eurjchem-1645	617	16	by	by	ADP
eurjchem-1645	617	17	reacting	react	VERB
eurjchem-1645	617	18	compound	compound	NOUN
eurjchem-1645	617	19	1	1	NUM
eurjchem-1645	617	20	with	with	ADP
eurjchem-1645	617	21	dmf‐dma	dmf‐dma	NOUN
eurjchem-1645	617	22	heating	heat	VERB
eurjchem-1645	617	23	at	at	ADP
eurjchem-1645	617	24	100	100	NUM
eurjchem-1645	617	25	°	°	ADP
eurjchem-1645	617	26	c	c	NOUN
eurjchem-1645	617	27	for	for	ADP
eurjchem-1645	617	28	obtaining	obtain	VERB
eurjchem-1645	617	29	compound	compound	NOUN
eurjchem-1645	617	30	2	2	NUM
eurjchem-1645	617	31	with	with	ADP
eurjchem-1645	617	32	78	78	NUM
eurjchem-1645	617	33	%	%	NOUN
eurjchem-1645	617	34	yield	yield	NOUN
eurjchem-1645	617	35	.	.	PUNCT
eurjchem-1645	618	1	the	the	DET
eurjchem-1645	618	2	compound	compound	NOUN
eurjchem-1645	618	3	2	2	NUM
eurjchem-1645	618	4	is	be	AUX
eurjchem-1645	618	5	reacted	react	VERB
eurjchem-1645	618	6	with	with	ADP
eurjchem-1645	618	7	n2h4.h2o	n2h4.h2o	NOUN
eurjchem-1645	618	8	in	in	ADP
eurjchem-1645	618	9	etoh	etoh	NOUN
eurjchem-1645	618	10	at	at	ADP
eurjchem-1645	618	11	80	80	NUM
eurjchem-1645	618	12	°	°	NUM
eurjchem-1645	618	13	c	c	NOUN
eurjchem-1645	618	14	for	for	ADP
eurjchem-1645	618	15	8	8	NUM
eurjchem-1645	618	16	h	h	NOUN
eurjchem-1645	618	17	to	to	PART
eurjchem-1645	618	18	obtain	obtain	VERB
eurjchem-1645	618	19	compound	compound	NOUN
eurjchem-1645	618	20	3	3	NUM
eurjchem-1645	618	21	with	with	ADP
eurjchem-1645	618	22	having	have	VERB
eurjchem-1645	618	23	68.3	68.3	NUM
eurjchem-1645	618	24	%	%	NOUN
eurjchem-1645	618	25	yield	yield	NOUN
eurjchem-1645	618	26	.	.	PUNCT
eurjchem-1645	619	1	the	the	DET
eurjchem-1645	619	2	structure	structure	NOUN
eurjchem-1645	619	3	of	of	ADP
eurjchem-1645	619	4	4,5,6,7‐	4,5,6,7‐	NUM
eurjchem-1645	619	5	tetrahydro‐1h‐pyrazolo[4,3‐c]pyridine	tetrahydro‐1h‐pyrazolo[4,3‐c]pyridine	PRON
eurjchem-1645	619	6	is	be	AUX
eurjchem-1645	619	7	confirmed	confirm	VERB
eurjchem-1645	619	8	by	by	ADP
eurjchem-1645	619	9	singlet	singlet	NOUN
eurjchem-1645	619	10	at	at	ADP
eurjchem-1645	619	11	δ	δ	PROPN
eurjchem-1645	619	12	7.31	7.31	NUM
eurjchem-1645	619	13	ppm	ppm	NOUN
eurjchem-1645	619	14	in	in	ADP
eurjchem-1645	619	15	1h	1h	NUM
eurjchem-1645	619	16	nmr	nmr	NOUN
eurjchem-1645	619	17	[	[	X
eurjchem-1645	619	18	16	16	NUM
eurjchem-1645	619	19	]	]	PUNCT
eurjchem-1645	619	20	.	.	PUNCT
eurjchem-1645	620	1	purification	purification	NOUN
eurjchem-1645	620	2	of	of	ADP
eurjchem-1645	620	3	the	the	DET
eurjchem-1645	620	4	compound	compound	NOUN
eurjchem-1645	620	5	3	3	NUM
eurjchem-1645	620	6	required	require	VERB
eurjchem-1645	620	7	purification	purification	NOUN
eurjchem-1645	620	8	by	by	ADP
eurjchem-1645	620	9	using	use	VERB
eurjchem-1645	620	10	column	column	NOUN
eurjchem-1645	620	11	chromatography	chromatography	NOUN
eurjchem-1645	620	12	.	.	PUNCT
eurjchem-1645	621	1	the	the	DET
eurjchem-1645	621	2	overall	overall	ADJ
eurjchem-1645	621	3	yield	yield	NOUN
eurjchem-1645	621	4	obtained	obtain	VERB
eurjchem-1645	621	5	by	by	ADP
eurjchem-1645	621	6	this	this	DET
eurjchem-1645	621	7	method	method	NOUN
eurjchem-1645	621	8	is	be	AUX
eurjchem-1645	621	9	greater	great	ADJ
eurjchem-1645	621	10	than	than	ADP
eurjchem-1645	621	11	earlier	early	ADJ
eurjchem-1645	621	12	reports	report	NOUN
eurjchem-1645	621	13	[	[	X
eurjchem-1645	621	14	13	13	NUM
eurjchem-1645	621	15	]	]	PUNCT
eurjchem-1645	621	16	.	.	PUNCT
eurjchem-1645	622	1	4,5,6,7‐tetrahydro‐1h‐pyrazolo[4,3‐c]pyridine	4,5,6,7‐tetrahydro‐1h‐pyrazolo[4,3‐c]pyridine	NUM
eurjchem-1645	622	2	(	(	PUNCT
eurjchem-1645	622	3	3	3	NUM
eurjchem-1645	622	4	)	)	PUNCT
eurjchem-1645	622	5	is	be	AUX
eurjchem-1645	622	6	reacted	react	VERB
eurjchem-1645	622	7	with	with	ADP
eurjchem-1645	622	8	di‐tert‐butyl	di‐tert‐butyl	PROPN
eurjchem-1645	622	9	dicarbonate	dicarbonate	NOUN
eurjchem-1645	622	10	(	(	PUNCT
eurjchem-1645	622	11	boc	boc	NOUN
eurjchem-1645	622	12	anhydride	anhydride	NOUN
eurjchem-1645	622	13	)	)	PUNCT
eurjchem-1645	622	14	using	use	VERB
eurjchem-1645	622	15	triethylamine	triethylamine	NOUN
eurjchem-1645	622	16	as	as	ADP
eurjchem-1645	622	17	base	base	NOUN
eurjchem-1645	622	18	to	to	PART
eurjchem-1645	622	19	obtain	obtain	VERB
eurjchem-1645	622	20	di‐tert‐butyl‐4,5‐di	di‐tert‐butyl‐4,5‐di	PROPN
eurjchem-1645	622	21	hydro‐7h‐pyrazolo[3,4‐c]pyridine‐1,6‐dicarboxylate	hydro‐7h‐pyrazolo[3,4‐c]pyridine‐1,6‐dicarboxylate	VERB
eurjchem-1645	622	22	(	(	PUNCT
eurjchem-1645	622	23	4	4	NUM
eurjchem-1645	622	24	)	)	PUNCT
eurjchem-1645	622	25	with	with	ADP
eurjchem-1645	622	26	yield	yield	NOUN
eurjchem-1645	622	27	91	91	NUM
eurjchem-1645	622	28	%	%	NOUN
eurjchem-1645	622	29	.	.	PUNCT
eurjchem-1645	623	1	the	the	DET
eurjchem-1645	623	2	compound	compound	NOUN
eurjchem-1645	623	3	4	4	NUM
eurjchem-1645	623	4	is	be	AUX
eurjchem-1645	623	5	having	have	VERB
eurjchem-1645	623	6	boc	boc	NOUN
eurjchem-1645	623	7	protection	protection	NOUN
eurjchem-1645	623	8	on	on	ADP
eurjchem-1645	623	9	both	both	DET
eurjchem-1645	623	10	nitrogen	nitrogen	PROPN
eurjchem-1645	623	11	’s	’s	PART
eurjchem-1645	623	12	confirmed	confirm	VERB
eurjchem-1645	623	13	by	by	ADP
eurjchem-1645	623	14	1h	1h	NUM
eurjchem-1645	623	15	nmr	nmr	NOUN
eurjchem-1645	623	16	showing	show	VERB
eurjchem-1645	623	17	singlet	singlet	NOUN
eurjchem-1645	623	18	for	for	ADP
eurjchem-1645	623	19	18	18	NUM
eurjchem-1645	623	20	h	h	NOUN
eurjchem-1645	623	21	at	at	ADP
eurjchem-1645	623	22	δ	δ	PROPN
eurjchem-1645	623	23	1.56	1.56	NUM
eurjchem-1645	623	24	ppm	ppm	NOUN
eurjchem-1645	623	25	.	.	PUNCT
eurjchem-1645	624	1	the	the	DET
eurjchem-1645	624	2	step	step	NOUN
eurjchem-1645	624	3	(	(	PUNCT
eurjchem-1645	624	4	d	d	X
eurjchem-1645	624	5	)	)	PUNCT
eurjchem-1645	624	6	is	be	AUX
eurjchem-1645	624	7	deportation	deportation	NOUN
eurjchem-1645	624	8	of	of	ADP
eurjchem-1645	624	9	aliphatic	aliphatic	ADJ
eurjchem-1645	624	10	n‐boc	n‐boc	NOUN
eurjchem-1645	624	11	which	which	PRON
eurjchem-1645	624	12	is	be	AUX
eurjchem-1645	624	13	achieved	achieve	VERB
eurjchem-1645	624	14	by	by	ADP
eurjchem-1645	624	15	treating	treat	VERB
eurjchem-1645	624	16	compound	compound	NOUN
eurjchem-1645	624	17	4	4	NUM
eurjchem-1645	624	18	with	with	ADP
eurjchem-1645	624	19	2	2	NUM
eurjchem-1645	624	20	n	n	PRON
eurjchem-1645	624	21	hcl	hcl	NOUN
eurjchem-1645	624	22	for	for	ADP
eurjchem-1645	624	23	2	2	NUM
eurjchem-1645	624	24	h	h	NOUN
eurjchem-1645	624	25	to	to	PART
eurjchem-1645	624	26	obtain	obtain	VERB
eurjchem-1645	624	27	compound	compound	NOUN
eurjchem-1645	624	28	5	5	NUM
eurjchem-1645	624	29	,	,	PUNCT
eurjchem-1645	624	30	confirmed	confirm	VERB
eurjchem-1645	624	31	by	by	ADP
eurjchem-1645	624	32	1h	1h	NUM
eurjchem-1645	624	33	nmr	nmr	NOUN
eurjchem-1645	624	34	showing	show	VERB
eurjchem-1645	624	35	singlet	singlet	NOUN
eurjchem-1645	624	36	for	for	ADP
eurjchem-1645	624	37	9	9	NUM
eurjchem-1645	624	38	h	h	NOUN
eurjchem-1645	624	39	at	at	ADP
eurjchem-1645	624	40	δ	δ	PROPN
eurjchem-1645	624	41	1.56	1.56	NUM
eurjchem-1645	624	42	ppm	ppm	NOUN
eurjchem-1645	624	43	.	.	PUNCT
eurjchem-1645	625	1	the	the	DET
eurjchem-1645	625	2	compound	compound	NOUN
eurjchem-1645	625	3	5	5	NUM
eurjchem-1645	625	4	was	be	AUX
eurjchem-1645	625	5	treated	treat	VERB
eurjchem-1645	625	6	with	with	ADP
eurjchem-1645	625	7	pyridine	pyridine	NOUN
eurjchem-1645	625	8	br2	br2	PROPN
eurjchem-1645	625	9	at	at	ADP
eurjchem-1645	625	10	room	room	NOUN
eurjchem-1645	625	11	temperature	temperature	NOUN
eurjchem-1645	625	12	for	for	ADP
eurjchem-1645	625	13	3	3	NUM
eurjchem-1645	625	14	h	h	NOUN
eurjchem-1645	625	15	to	to	PART
eurjchem-1645	625	16	obtain	obtain	VERB
eurjchem-1645	625	17	compound	compound	NOUN
eurjchem-1645	625	18	6	6	NUM
eurjchem-1645	625	19	with	with	ADP
eurjchem-1645	625	20	92	92	NUM
eurjchem-1645	625	21	%	%	NOUN
eurjchem-1645	625	22	yield	yield	NOUN
eurjchem-1645	625	23	.	.	PUNCT
eurjchem-1645	626	1	the	the	DET
eurjchem-1645	626	2	structure	structure	NOUN
eurjchem-1645	626	3	of	of	ADP
eurjchem-1645	626	4	tert‐butyl‐3‐bromo‐4,5,6,7‐tetra	tert‐butyl‐3‐bromo‐4,5,6,7‐tetra	PROPN
eurjchem-1645	626	5	hydropyrazolo[3,4‐c]pyridine‐1‐carboxylate	hydropyrazolo[3,4‐c]pyridine‐1‐carboxylate	NOUN
eurjchem-1645	626	6	(	(	PUNCT
eurjchem-1645	626	7	6	6	NUM
eurjchem-1645	626	8	)	)	PUNCT
eurjchem-1645	626	9	was	be	AUX
eurjchem-1645	626	10	confir‐	confir‐	NOUN
eurjchem-1645	626	11	med	me	VERB
eurjchem-1645	626	12	by	by	ADP
eurjchem-1645	626	13	disappearance	disappearance	NOUN
eurjchem-1645	626	14	of	of	ADP
eurjchem-1645	626	15	singlet	singlet	NOUN
eurjchem-1645	626	16	at	at	ADP
eurjchem-1645	626	17	δ	δ	PROPN
eurjchem-1645	626	18	7.31	7.31	NUM
eurjchem-1645	626	19	ppm	ppm	NOUN
eurjchem-1645	626	20	in	in	ADP
eurjchem-1645	626	21	1h	1h	NUM
eurjchem-1645	626	22	nmr	nmr	NOUN
eurjchem-1645	626	23	.	.	PUNCT
eurjchem-1645	627	1	the	the	DET
eurjchem-1645	627	2	compound	compound	NOUN
eurjchem-1645	627	3	6	6	NUM
eurjchem-1645	627	4	reacted	react	VERB
eurjchem-1645	627	5	with	with	ADP
eurjchem-1645	627	6	aqueous	aqueous	ADJ
eurjchem-1645	627	7	naoh	naoh	NOUN
eurjchem-1645	627	8	in	in	ADP
eurjchem-1645	627	9	heating	heating	NOUN
eurjchem-1645	627	10	for	for	ADP
eurjchem-1645	627	11	3	3	NUM
eurjchem-1645	627	12	h.	h.	NOUN
eurjchem-1645	627	13	there	there	PRON
eurjchem-1645	627	14	is	be	VERB
eurjchem-1645	627	15	formation	formation	NOUN
eurjchem-1645	627	16	of	of	ADP
eurjchem-1645	627	17	compound	compound	NOUN
eurjchem-1645	627	18	7	7	NUM
eurjchem-1645	627	19	in	in	ADP
eurjchem-1645	627	20	88.4	88.4	NUM
eurjchem-1645	627	21	%	%	NOUN
eurjchem-1645	627	22	yield	yield	NOUN
eurjchem-1645	627	23	which	which	PRON
eurjchem-1645	627	24	is	be	AUX
eurjchem-1645	627	25	confirmed	confirm	VERB
eurjchem-1645	627	26	by	by	ADP
eurjchem-1645	627	27	desired	desire	VERB
eurjchem-1645	627	28	mass	mass	NOUN
eurjchem-1645	627	29	in	in	ADP
eurjchem-1645	627	30	lc‐ms	lc‐ms	NUM
eurjchem-1645	627	31	.	.	PUNCT
eurjchem-1645	628	1	the	the	DET
eurjchem-1645	628	2	compound	compound	NOUN
eurjchem-1645	628	3	7	7	NUM
eurjchem-1645	628	4	is	be	AUX
eurjchem-1645	628	5	protected	protect	VERB
eurjchem-1645	628	6	by	by	ADP
eurjchem-1645	628	7	using	use	VERB
eurjchem-1645	628	8	benzylbromide	benzylbromide	NOUN
eurjchem-1645	628	9	in	in	ADP
eurjchem-1645	628	10	thf	thf	NOUN
eurjchem-1645	628	11	by	by	ADP
eurjchem-1645	628	12	using	use	VERB
eurjchem-1645	628	13	mixture	mixture	NOUN
eurjchem-1645	628	14	of	of	ADP
eurjchem-1645	628	15	bases	basis	NOUN
eurjchem-1645	628	16	as	as	ADP
eurjchem-1645	628	17	2,6‐leutidine	2,6‐leutidine	NUM
eurjchem-1645	628	18	and	and	CCONJ
eurjchem-1645	628	19	dmap	dmap	NOUN
eurjchem-1645	628	20	at	at	ADP
eurjchem-1645	628	21	room	room	NOUN
eurjchem-1645	628	22	temperature	temperature	NOUN
eurjchem-1645	628	23	for	for	ADP
eurjchem-1645	628	24	compound	compound	NOUN
eurjchem-1645	628	25	6h	6h	NOUN
eurjchem-1645	628	26	to	to	PART
eurjchem-1645	628	27	obtain	obtain	VERB
eurjchem-1645	628	28	compound	compound	NOUN
eurjchem-1645	628	29	8	8	NUM
eurjchem-1645	628	30	with	with	ADP
eurjchem-1645	628	31	83	83	NUM
eurjchem-1645	628	32	%	%	NOUN
eurjchem-1645	628	33	yield	yield	NOUN
eurjchem-1645	628	34	,	,	PUNCT
eurjchem-1645	628	35	with	with	ADP
eurjchem-1645	628	36	1h	1h	NUM
eurjchem-1645	628	37	nmr	nmr	NOUN
eurjchem-1645	628	38	signals	signal	NOUN
eurjchem-1645	628	39	at	at	ADP
eurjchem-1645	628	40	δ	δ	PROPN
eurjchem-1645	628	41	7.38‐7.28	7.38‐7.28	NUM
eurjchem-1645	628	42	ppm	ppm	NOUN
eurjchem-1645	628	43	(	(	PUNCT
eurjchem-1645	628	44	m	m	PROPN
eurjchem-1645	628	45	,	,	PUNCT
eurjchem-1645	628	46	5h	5h	NUM
eurjchem-1645	628	47	)	)	PUNCT
eurjchem-1645	628	48	.	.	PUNCT
eurjchem-1645	629	1	the	the	DET
eurjchem-1645	629	2	compound	compound	NOUN
eurjchem-1645	629	3	8	8	NUM
eurjchem-1645	629	4	having	have	VERB
eurjchem-1645	629	5	free	free	ADJ
eurjchem-1645	629	6	hydroxyl	hydroxyl	NOUN
eurjchem-1645	629	7	group	group	NOUN
eurjchem-1645	629	8	which	which	PRON
eurjchem-1645	629	9	is	be	AUX
eurjchem-1645	629	10	protected	protect	VERB
eurjchem-1645	629	11	by	by	ADP
eurjchem-1645	629	12	using	use	VERB
eurjchem-1645	629	13	triflic	triflic	ADJ
eurjchem-1645	629	14	anhydride	anhydride	NOUN
eurjchem-1645	629	15	at	at	ADP
eurjchem-1645	629	16	room	room	NOUN
eurjchem-1645	629	17	temperature	temperature	NOUN
eurjchem-1645	629	18	for	for	ADP
eurjchem-1645	629	19	12	12	NUM
eurjchem-1645	629	20	h	h	NOUN
eurjchem-1645	629	21	to	to	PART
eurjchem-1645	629	22	obtain	obtain	VERB
eurjchem-1645	629	23	compound	compound	NOUN
eurjchem-1645	629	24	9	9	NUM
eurjchem-1645	629	25	with	with	ADP
eurjchem-1645	629	26	88.5	88.5	NUM
eurjchem-1645	629	27	%	%	NOUN
eurjchem-1645	629	28	yield	yield	NOUN
eurjchem-1645	629	29	.	.	PUNCT
eurjchem-1645	630	1	t‐butyl	t‐butyl	NUM
eurjchem-1645	630	2	3‐(2,2,2‐trifluoroacetoyloxy)‐6‐	3‐(2,2,2‐trifluoroacetoyloxy)‐6‐	NUM
eurjchem-1645	630	3	benzyl‐4,5,6,7‐tetrahydropyrazolo[3	benzyl‐4,5,6,7‐tetrahydropyrazolo[3	NOUN
eurjchem-1645	630	4	,	,	PUNCT
eurjchem-1645	630	5	4‐c]pyridine‐1‐carboxy‐	4‐c]pyridine‐1‐carboxy‐	NUM
eurjchem-1645	630	6	late	late	ADJ
eurjchem-1645	630	7	(	(	PUNCT
eurjchem-1645	630	8	9	9	NUM
eurjchem-1645	630	9	)	)	PUNCT
eurjchem-1645	630	10	is	be	AUX
eurjchem-1645	630	11	key	key	ADJ
eurjchem-1645	630	12	intermediate	intermediate	ADJ
eurjchem-1645	630	13	for	for	ADP
eurjchem-1645	630	14	the	the	DET
eurjchem-1645	630	15	synthesis	synthesis	NOUN
eurjchem-1645	630	16	of	of	ADP
eurjchem-1645	630	17	final	final	ADJ
eurjchem-1645	630	18	com‐	com‐	ADJ
eurjchem-1645	630	19	pounds	pound	NOUN
eurjchem-1645	630	20	13a‐h	13a‐h	NOUN
eurjchem-1645	630	21	and	and	CCONJ
eurjchem-1645	630	22	15a‐h	15a‐h	NOUN
eurjchem-1645	630	23	.	.	PUNCT
eurjchem-1645	631	1	the	the	DET
eurjchem-1645	631	2	compound	compound	NOUN
eurjchem-1645	631	3	9	9	NUM
eurjchem-1645	631	4	was	be	AUX
eurjchem-1645	631	5	treated	treat	VERB
eurjchem-1645	631	6	with	with	ADP
eurjchem-1645	631	7	different	different	ADJ
eurjchem-1645	631	8	aromatic	aromatic	ADJ
eurjchem-1645	631	9	boranic	boranic	ADJ
eurjchem-1645	631	10	acids	acid	NOUN
eurjchem-1645	631	11	at	at	ADP
eurjchem-1645	631	12	100	100	NUM
eurjchem-1645	631	13	°	°	ADP
eurjchem-1645	631	14	c	c	NOUN
eurjchem-1645	631	15	for	for	ADP
eurjchem-1645	631	16	6	6	NUM
eurjchem-1645	631	17	h	h	NOUN
eurjchem-1645	631	18	to	to	PART
eurjchem-1645	631	19	obtain	obtain	VERB
eurjchem-1645	631	20	compounds	compound	NOUN
eurjchem-1645	631	21	10a‐d	10a‐d	NOUN
eurjchem-1645	631	22	with	with	ADP
eurjchem-1645	631	23	yields	yield	NOUN
eurjchem-1645	631	24	in	in	ADP
eurjchem-1645	631	25	the	the	DET
eurjchem-1645	631	26	range	range	NOUN
eurjchem-1645	631	27	from	from	ADP
eurjchem-1645	631	28	63	63	NUM
eurjchem-1645	631	29	to	to	PART
eurjchem-1645	631	30	83	83	NUM
eurjchem-1645	631	31	%	%	NOUN
eurjchem-1645	631	32	yields	yield	NOUN
eurjchem-1645	631	33	after	after	ADP
eurjchem-1645	631	34	purifications	purification	NOUN
eurjchem-1645	631	35	by	by	ADP
eurjchem-1645	631	36	silica	silica	NOUN
eurjchem-1645	631	37	gel	gel	NOUN
eurjchem-1645	631	38	(	(	PUNCT
eurjchem-1645	631	39	100‐200	100‐200	NUM
eurjchem-1645	631	40	mesh	mesh	NOUN
eurjchem-1645	631	41	)	)	PUNCT
eurjchem-1645	631	42	column	column	NOUN
eurjchem-1645	631	43	chromatography	chromatography	NOUN
eurjchem-1645	631	44	.	.	PUNCT
eurjchem-1645	632	1	debenzylation	debenzylation	NOUN
eurjchem-1645	632	2	of	of	ADP
eurjchem-1645	632	3	compounds	compound	NOUN
eurjchem-1645	632	4	10a‐d	10a‐d	NOUN
eurjchem-1645	632	5	was	be	AUX
eurjchem-1645	632	6	done	do	VERB
eurjchem-1645	632	7	by	by	ADP
eurjchem-1645	632	8	using	use	VERB
eurjchem-1645	632	9	pd	pd	PROPN
eurjchem-1645	632	10	/	/	SYM
eurjchem-1645	632	11	c	c	PROPN
eurjchem-1645	632	12	in	in	ADP
eurjchem-1645	632	13	etoh	etoh	NOUN
eurjchem-1645	632	14	for	for	ADP
eurjchem-1645	632	15	50	50	NUM
eurjchem-1645	632	16	psi	psi	NOUN
eurjchem-1645	632	17	of	of	ADP
eurjchem-1645	632	18	hydrogen	hydrogen	NOUN
eurjchem-1645	632	19	for	for	ADP
eurjchem-1645	632	20	3	3	NUM
eurjchem-1645	632	21	h	h	NOUN
eurjchem-1645	632	22	at	at	ADP
eurjchem-1645	632	23	room	room	NOUN
eurjchem-1645	632	24	temperature	temperature	NOUN
eurjchem-1645	632	25	to	to	PART
eurjchem-1645	632	26	obtain	obtain	VERB
eurjchem-1645	632	27	compounds	compound	NOUN
eurjchem-1645	632	28	11a‐d	11a‐d	NOUN
eurjchem-1645	632	29	with	with	ADP
eurjchem-1645	632	30	84	84	NUM
eurjchem-1645	632	31	to	to	PART
eurjchem-1645	632	32	90	90	NUM
eurjchem-1645	632	33	%	%	NOUN
eurjchem-1645	632	34	yields	yield	NOUN
eurjchem-1645	632	35	.	.	PUNCT
eurjchem-1645	633	1	alkylation	alkylation	NOUN
eurjchem-1645	633	2	of	of	ADP
eurjchem-1645	633	3	compounds	compound	NOUN
eurjchem-1645	633	4	11a‐d	11a‐d	PROPN
eurjchem-1645	633	5	was	be	AUX
eurjchem-1645	633	6	done	do	VERB
eurjchem-1645	633	7	by	by	ADP
eurjchem-1645	633	8	using	use	VERB
eurjchem-1645	633	9	substituted	substitute	VERB
eurjchem-1645	633	10	aromatic	aromatic	ADJ
eurjchem-1645	633	11	bromides	bromide	NOUN
eurjchem-1645	633	12	in	in	ADP
eurjchem-1645	633	13	thf	thf	NOUN
eurjchem-1645	633	14	by	by	ADP
eurjchem-1645	633	15	using	use	VERB
eurjchem-1645	633	16	mixed	mixed	ADJ
eurjchem-1645	633	17	bases	basis	NOUN
eurjchem-1645	633	18	2,6‐leutidine	2,6‐leutidine	NUM
eurjchem-1645	633	19	and	and	CCONJ
eurjchem-1645	633	20	dmap	dmap	VERB
eurjchem-1645	633	21	for	for	ADP
eurjchem-1645	633	22	3	3	NUM
eurjchem-1645	633	23	h	h	NOUN
eurjchem-1645	633	24	at	at	ADP
eurjchem-1645	633	25	room	room	NOUN
eurjchem-1645	633	26	temperature	temperature	NOUN
eurjchem-1645	633	27	to	to	PART
eurjchem-1645	633	28	obtain	obtain	VERB
eurjchem-1645	633	29	compounds	compound	NOUN
eurjchem-1645	633	30	12a‐h	12a‐h	NOUN
eurjchem-1645	633	31	with	with	ADP
eurjchem-1645	633	32	yields	yield	NOUN
eurjchem-1645	633	33	84	84	NUM
eurjchem-1645	633	34	to	to	PART
eurjchem-1645	633	35	93	93	NUM
eurjchem-1645	633	36	%	%	NOUN
eurjchem-1645	633	37	.	.	PUNCT
eurjchem-1645	634	1	the	the	DET
eurjchem-1645	634	2	cleavage	cleavage	NOUN
eurjchem-1645	634	3	of	of	ADP
eurjchem-1645	634	4	protecting	protect	VERB
eurjchem-1645	634	5	group	group	NOUN
eurjchem-1645	634	6	of	of	ADP
eurjchem-1645	634	7	compounds	compound	NOUN
eurjchem-1645	634	8	12a‐h	12a‐h	NOUN
eurjchem-1645	634	9	was	be	AUX
eurjchem-1645	634	10	done	do	VERB
eurjchem-1645	634	11	by	by	ADP
eurjchem-1645	634	12	using	use	VERB
eurjchem-1645	634	13	aqueous	aqueous	ADJ
eurjchem-1645	634	14	6	6	NUM
eurjchem-1645	634	15	n	n	NOUN
eurjchem-1645	634	16	hcl	hcl	PROPN
eurjchem-1645	634	17	at	at	ADP
eurjchem-1645	634	18	room	room	NOUN
eurjchem-1645	634	19	temperature	temperature	NOUN
eurjchem-1645	634	20	for	for	ADP
eurjchem-1645	634	21	6	6	NUM
eurjchem-1645	634	22	h	h	NOUN
eurjchem-1645	634	23	to	to	PART
eurjchem-1645	634	24	obtain	obtain	VERB
eurjchem-1645	634	25	compounds	compound	NOUN
eurjchem-1645	634	26	13a‐h	13a‐h	NOUN
eurjchem-1645	634	27	with	with	ADP
eurjchem-1645	634	28	yields	yield	NOUN
eurjchem-1645	634	29	76	76	NUM
eurjchem-1645	634	30	to	to	PART
eurjchem-1645	634	31	91	91	NUM
eurjchem-1645	634	32	%	%	NOUN
eurjchem-1645	634	33	.	.	PUNCT
eurjchem-1645	635	1	the	the	DET
eurjchem-1645	635	2	mixed	mixed	ADJ
eurjchem-1645	635	3	bases	basis	NOUN
eurjchem-1645	635	4	used	use	VERB
eurjchem-1645	635	5	in	in	ADP
eurjchem-1645	635	6	steps	step	NOUN
eurjchem-1645	635	7	(	(	PUNCT
eurjchem-1645	635	8	g	g	NOUN
eurjchem-1645	635	9	)	)	PUNCT
eurjchem-1645	635	10	and	and	CCONJ
eurjchem-1645	635	11	(	(	PUNCT
eurjchem-1645	635	12	k	k	NOUN
eurjchem-1645	635	13	)	)	PUNCT
eurjchem-1645	635	14	to	to	PART
eurjchem-1645	635	15	enhance	enhance	VERB
eurjchem-1645	635	16	the	the	DET
eurjchem-1645	635	17	reactivity	reactivity	NOUN
eurjchem-1645	635	18	of	of	ADP
eurjchem-1645	635	19	secondary	secondary	ADJ
eurjchem-1645	635	20	amine	amine	NOUN
eurjchem-1645	635	21	used	use	VERB
eurjchem-1645	635	22	for	for	ADP
eurjchem-1645	635	23	reaction	reaction	NOUN
eurjchem-1645	635	24	.	.	PUNCT
eurjchem-1645	636	1	in	in	ADP
eurjchem-1645	636	2	scheme	scheme	NOUN
eurjchem-1645	636	3	2	2	NUM
eurjchem-1645	636	4	,	,	PUNCT
eurjchem-1645	636	5	compounds	compound	NOUN
eurjchem-1645	636	6	12a‐h	12a‐h	NOUN
eurjchem-1645	636	7	are	be	AUX
eurjchem-1645	636	8	treated	treat	VERB
eurjchem-1645	636	9	with	with	ADP
eurjchem-1645	636	10	kmno4	kmno4	NOUN
eurjchem-1645	636	11	in	in	ADP
eurjchem-1645	636	12	dcm	dcm	PROPN
eurjchem-1645	636	13	and	and	CCONJ
eurjchem-1645	636	14	18‐crown‐6	18‐crown‐6	NUM
eurjchem-1645	636	15	used	use	VERB
eurjchem-1645	636	16	as	as	ADP
eurjchem-1645	636	17	phase	phase	NOUN
eurjchem-1645	636	18	transfer	transfer	NOUN
eurjchem-1645	636	19	catalyst	catalyst	NOUN
eurjchem-1645	636	20	at	at	ADP
eurjchem-1645	636	21	room	room	NOUN
eurjchem-1645	636	22	temperature	temperature	NOUN
eurjchem-1645	636	23	for	for	ADP
eurjchem-1645	636	24	6	6	NUM
eurjchem-1645	636	25	h	h	NOUN
eurjchem-1645	636	26	to	to	PART
eurjchem-1645	636	27	give	give	VERB
eurjchem-1645	636	28	compounds	compound	NOUN
eurjchem-1645	636	29	14a‐h	14a‐h	PROPN
eurjchem-1645	636	30	with	with	ADP
eurjchem-1645	636	31	yields	yield	NOUN
eurjchem-1645	636	32	71	71	NUM
eurjchem-1645	636	33	to	to	PART
eurjchem-1645	636	34	78	78	NUM
eurjchem-1645	636	35	%	%	NOUN
eurjchem-1645	636	36	,	,	PUNCT
eurjchem-1645	636	37	which	which	PRON
eurjchem-1645	636	38	is	be	AUX
eurjchem-1645	636	39	confirmed	confirm	VERB
eurjchem-1645	636	40	by	by	ADP
eurjchem-1645	636	41	vanishing	vanish	VERB
eurjchem-1645	636	42	singlet	singlet	NOUN
eurjchem-1645	636	43	at	at	ADP
eurjchem-1645	636	44	3.78	3.78	NUM
eurjchem-1645	636	45	in	in	ADP
eurjchem-1645	636	46	1h	1h	NUM
eurjchem-1645	636	47	nmr	nmr	NOUN
eurjchem-1645	636	48	.	.	PUNCT
eurjchem-1645	637	1	the	the	DET
eurjchem-1645	637	2	compound	compound	NOUN
eurjchem-1645	637	3	14a‐h	14a‐h	NOUN
eurjchem-1645	637	4	are	be	AUX
eurjchem-1645	637	5	converted	convert	VERB
eurjchem-1645	637	6	to	to	ADP
eurjchem-1645	637	7	compounds	compound	NOUN
eurjchem-1645	637	8	15a‐	15a‐	NUM
eurjchem-1645	637	9	h	h	NOUN
eurjchem-1645	637	10	by	by	ADP
eurjchem-1645	637	11	using	use	VERB
eurjchem-1645	637	12	aqueous	aqueous	ADJ
eurjchem-1645	637	13	6	6	NUM
eurjchem-1645	637	14	n	n	NOUN
eurjchem-1645	637	15	hcl	hcl	PROPN
eurjchem-1645	637	16	at	at	ADP
eurjchem-1645	637	17	room	room	NOUN
eurjchem-1645	637	18	temperature	temperature	NOUN
eurjchem-1645	637	19	for	for	ADP
eurjchem-1645	637	20	6	6	NUM
eurjchem-1645	637	21	h	h	NOUN
eurjchem-1645	637	22	with	with	ADP
eurjchem-1645	637	23	79	79	NUM
eurjchem-1645	637	24	to	to	PART
eurjchem-1645	637	25	92	92	NUM
eurjchem-1645	637	26	%	%	NOUN
eurjchem-1645	637	27	yields	yield	NOUN
eurjchem-1645	637	28	.	.	PUNCT
eurjchem-1645	638	1	the	the	DET
eurjchem-1645	638	2	final	final	ADJ
eurjchem-1645	638	3	compounds	compound	NOUN
eurjchem-1645	638	4	13a‐h	13a‐h	NOUN
eurjchem-1645	638	5	and	and	CCONJ
eurjchem-1645	638	6	15a‐h	15a‐h	NOUN
eurjchem-1645	638	7	are	be	AUX
eurjchem-1645	638	8	obtained	obtain	VERB
eurjchem-1645	638	9	with	with	ADP
eurjchem-1645	638	10	reaction	reaction	NOUN
eurjchem-1645	638	11	yields	yield	NOUN
eurjchem-1645	638	12	76	76	NUM
eurjchem-1645	638	13	to	to	PART
eurjchem-1645	638	14	92	92	NUM
eurjchem-1645	638	15	%	%	NOUN
eurjchem-1645	638	16	.	.	PUNCT
eurjchem-1645	639	1	purity	purity	NOUN
eurjchem-1645	639	2	of	of	ADP
eurjchem-1645	639	3	all	all	DET
eurjchem-1645	639	4	final	final	ADJ
eurjchem-1645	639	5	compounds	compound	NOUN
eurjchem-1645	639	6	and	and	CCONJ
eurjchem-1645	639	7	key	key	ADJ
eurjchem-1645	639	8	intermediates	intermediate	NOUN
eurjchem-1645	639	9	is	be	AUX
eurjchem-1645	639	10	>	>	X
eurjchem-1645	639	11	95	95	NUM
eurjchem-1645	639	12	%	%	NOUN
eurjchem-1645	639	13	which	which	PRON
eurjchem-1645	639	14	are	be	AUX
eurjchem-1645	639	15	further	far	ADV
eurjchem-1645	639	16	used	use	VERB
eurjchem-1645	639	17	for	for	ADP
eurjchem-1645	639	18	biological	biological	ADJ
eurjchem-1645	639	19	activity	activity	NOUN
eurjchem-1645	639	20	studies	study	NOUN
eurjchem-1645	639	21	.	.	PUNCT
eurjchem-1645	640	1	408	408	NUM
eurjchem-1645	640	2	pawar	pawar	PROPN
eurjchem-1645	640	3	et	et	PROPN
eurjchem-1645	640	4	al	al	PROPN
eurjchem-1645	640	5	.	.	PUNCT
eurjchem-1645	640	6	/	/	SYM
eurjchem-1645	640	7	european	european	PROPN
eurjchem-1645	640	8	journal	journal	PROPN
eurjchem-1645	640	9	of	of	ADP
eurjchem-1645	640	10	chemistry	chemistry	NOUN
eurjchem-1645	640	11	8	8	NUM
eurjchem-1645	640	12	(	(	PUNCT
eurjchem-1645	640	13	4	4	NUM
eurjchem-1645	640	14	)	)	PUNCT
eurjchem-1645	640	15	(	(	PUNCT
eurjchem-1645	640	16	2017	2017	NUM
eurjchem-1645	640	17	)	)	PUNCT
eurjchem-1645	640	18	400‐409	400‐409	NUM
eurjchem-1645	640	19	table	table	NOUN
eurjchem-1645	640	20	2	2	NUM
eurjchem-1645	640	21	.	.	PUNCT
eurjchem-1645	640	22	inhibitory	inhibitory	ADJ
eurjchem-1645	640	23	activity	activity	NOUN
eurjchem-1645	640	24	of	of	ADP
eurjchem-1645	640	25	compound	compound	NOUN
eurjchem-1645	640	26	13c	13c	NOUN
eurjchem-1645	640	27	,	,	PUNCT
eurjchem-1645	640	28	13	13	NUM
eurjchem-1645	640	29	g	g	NOUN
eurjchem-1645	640	30	,	,	PUNCT
eurjchem-1645	640	31	15	15	NUM
eurjchem-1645	640	32	g	g	NOUN
eurjchem-1645	640	33	and	and	CCONJ
eurjchem-1645	640	34	15h	15h	NUM
eurjchem-1645	640	35	against	against	ADP
eurjchem-1645	640	36	panel	panel	NOUN
eurjchem-1645	640	37	of	of	ADP
eurjchem-1645	640	38	eight	eight	NUM
eurjchem-1645	640	39	human	human	ADJ
eurjchem-1645	640	40	kinases	kinase	NOUN
eurjchem-1645	640	41	.	.	PUNCT
eurjchem-1645	641	1	kinase	kinase	PROPN
eurjchem-1645	641	2	%	%	NOUN
eurjchem-1645	641	3	inhibition	inhibition	NOUN
eurjchem-1645	641	4	compound	compound	NOUN
eurjchem-1645	641	5	13c	13c	NOUN
eurjchem-1645	641	6	compound	compound	VERB
eurjchem-1645	641	7	13	13	NUM
eurjchem-1645	641	8	g	g	NOUN
eurjchem-1645	641	9	compound	compound	NOUN
eurjchem-1645	641	10	15	15	NUM
eurjchem-1645	641	11	g	g	NOUN
eurjchem-1645	641	12	compound	compound	NOUN
eurjchem-1645	641	13	15h	15h	PROPN
eurjchem-1645	641	14	aurora‐a	aurora‐a	PROPN
eurjchem-1645	641	15	73	73	NUM
eurjchem-1645	641	16	64	64	NUM
eurjchem-1645	641	17	51	51	NUM
eurjchem-1645	641	18	57	57	NUM
eurjchem-1645	641	19	aurora‐b	aurora‐b	NOUN
eurjchem-1645	641	20	41	41	NUM
eurjchem-1645	641	21	70	70	NUM
eurjchem-1645	641	22	77	77	NUM
eurjchem-1645	641	23	73	73	NUM
eurjchem-1645	641	24	cdk2	cdk2	PROPN
eurjchem-1645	641	25	/	/	SYM
eurjchem-1645	641	26	cyclina	cyclina	PROPN
eurjchem-1645	641	27	28	28	NUM
eurjchem-1645	641	28	37	37	NUM
eurjchem-1645	641	29	23	23	NUM
eurjchem-1645	641	30	33	33	NUM
eurjchem-1645	641	31	cdk2	cdk2	PROPN
eurjchem-1645	641	32	/	/	SYM
eurjchem-1645	641	33	cycline	cycline	PROPN
eurjchem-1645	641	34	17	17	NUM
eurjchem-1645	641	35	22	22	NUM
eurjchem-1645	641	36	21	21	NUM
eurjchem-1645	641	37	23	23	NUM
eurjchem-1645	641	38	cdk5	cdk5	PROPN
eurjchem-1645	641	39	/	/	SYM
eurjchem-1645	641	40	p25	p25	PROPN
eurjchem-1645	641	41	66	66	NUM
eurjchem-1645	641	42	59	59	NUM
eurjchem-1645	641	43	70	70	NUM
eurjchem-1645	641	44	56	56	NUM
eurjchem-1645	641	45	egfr	egfr	NOUN
eurjchem-1645	641	46	14	14	NUM
eurjchem-1645	641	47	21	21	NUM
eurjchem-1645	641	48	15	15	NUM
eurjchem-1645	641	49	18	18	NUM
eurjchem-1645	641	50	mtor	mtor	NOUN
eurjchem-1645	641	51	44	44	NUM
eurjchem-1645	641	52	68	68	NUM
eurjchem-1645	641	53	46	46	NUM
eurjchem-1645	641	54	48	48	NUM
eurjchem-1645	641	55	pdk1	pdk1	NOUN
eurjchem-1645	641	56	23	23	NUM
eurjchem-1645	641	57	28	28	NUM
eurjchem-1645	641	58	19	19	NUM
eurjchem-1645	641	59	33	33	NUM
eurjchem-1645	641	60	3.2	3.2	NUM
eurjchem-1645	641	61	.	.	PUNCT
eurjchem-1645	642	1	biological	biological	ADJ
eurjchem-1645	642	2	studies	study	NOUN
eurjchem-1645	642	3	all	all	DET
eurjchem-1645	642	4	the	the	DET
eurjchem-1645	642	5	newly	newly	ADV
eurjchem-1645	642	6	synthesized	synthesize	VERB
eurjchem-1645	642	7	compounds	compound	NOUN
eurjchem-1645	642	8	13a‐h	13a‐h	NOUN
eurjchem-1645	642	9	and	and	CCONJ
eurjchem-1645	642	10	15a‐h	15a‐h	NOUN
eurjchem-1645	642	11	were	be	AUX
eurjchem-1645	642	12	evaluated	evaluate	VERB
eurjchem-1645	642	13	for	for	ADP
eurjchem-1645	642	14	their	their	PRON
eurjchem-1645	642	15	antiproliferative	antiproliferative	ADJ
eurjchem-1645	642	16	activities	activity	NOUN
eurjchem-1645	642	17	against	against	ADP
eurjchem-1645	642	18	a	a	DET
eurjchem-1645	642	19	panel	panel	NOUN
eurjchem-1645	642	20	of	of	ADP
eurjchem-1645	642	21	four	four	NUM
eurjchem-1645	642	22	different	different	ADJ
eurjchem-1645	642	23	human	human	ADJ
eurjchem-1645	642	24	cancer	cancer	NOUN
eurjchem-1645	642	25	cell	cell	NOUN
eurjchem-1645	642	26	lines	line	NOUN
eurjchem-1645	642	27	.	.	PUNCT
eurjchem-1645	643	1	the	the	DET
eurjchem-1645	643	2	ic50	ic50	PROPN
eurjchem-1645	643	3	for	for	ADP
eurjchem-1645	643	4	each	each	DET
eurjchem-1645	643	5	synthesized	synthesize	VERB
eurjchem-1645	643	6	compounds	compound	NOUN
eurjchem-1645	643	7	are	be	AUX
eurjchem-1645	643	8	calculated	calculate	VERB
eurjchem-1645	643	9	with	with	ADP
eurjchem-1645	643	10	respect	respect	NOUN
eurjchem-1645	643	11	to	to	ADP
eurjchem-1645	643	12	one	one	NUM
eurjchem-1645	643	13	human	human	ADJ
eurjchem-1645	643	14	normal	normal	ADJ
eurjchem-1645	643	15	cell	cell	NOUN
eurjchem-1645	643	16	line	line	NOUN
eurjchem-1645	643	17	human	human	ADJ
eurjchem-1645	643	18	umbilical	umbilical	ADJ
eurjchem-1645	643	19	vein	vein	ADJ
eurjchem-1645	643	20	endothelial	endothelial	ADJ
eurjchem-1645	643	21	cell	cell	NOUN
eurjchem-1645	643	22	line	line	NOUN
eurjchem-1645	643	23	(	(	PUNCT
eurjchem-1645	643	24	atcc	atcc	PROPN
eurjchem-1645	643	25	crl‐1730	crl‐1730	PROPN
eurjchem-1645	643	26	)	)	PUNCT
eurjchem-1645	643	27	and	and	CCONJ
eurjchem-1645	643	28	results	result	NOUN
eurjchem-1645	643	29	are	be	AUX
eurjchem-1645	643	30	summarized	summarize	VERB
eurjchem-1645	643	31	in	in	ADP
eurjchem-1645	643	32	table	table	NOUN
eurjchem-1645	643	33	1	1	NUM
eurjchem-1645	643	34	.	.	PUNCT
eurjchem-1645	644	1	these	these	DET
eurjchem-1645	644	2	values	value	NOUN
eurjchem-1645	644	3	represent	represent	VERB
eurjchem-1645	644	4	the	the	DET
eurjchem-1645	644	5	concentration	concentration	NOUN
eurjchem-1645	644	6	required	require	VERB
eurjchem-1645	644	7	to	to	PART
eurjchem-1645	644	8	inhibit	inhibit	VERB
eurjchem-1645	644	9	50	50	NUM
eurjchem-1645	644	10	%	%	NOUN
eurjchem-1645	644	11	cell	cell	NOUN
eurjchem-1645	644	12	population	population	NOUN
eurjchem-1645	644	13	compared	compare	VERB
eurjchem-1645	644	14	with	with	ADP
eurjchem-1645	644	15	the	the	DET
eurjchem-1645	644	16	control	control	NOUN
eurjchem-1645	644	17	cells	cell	NOUN
eurjchem-1645	644	18	treated	treat	VERB
eurjchem-1645	644	19	with	with	ADP
eurjchem-1645	644	20	dmso	dmso	NOUN
eurjchem-1645	644	21	and	and	CCONJ
eurjchem-1645	644	22	positive	positive	ADJ
eurjchem-1645	644	23	control	control	NOUN
eurjchem-1645	644	24	doxorubicin	doxorubicin	VERB
eurjchem-1645	644	25	under	under	ADP
eurjchem-1645	644	26	similar	similar	ADJ
eurjchem-1645	644	27	conditions	condition	NOUN
eurjchem-1645	644	28	.	.	PUNCT
eurjchem-1645	645	1	from	from	ADP
eurjchem-1645	645	2	substituted	substitute	VERB
eurjchem-1645	645	3	tetra‐hydro‐6‐(substituted)‐1h‐pyra‐	tetra‐hydro‐6‐(substituted)‐1h‐pyra‐	NOUN
eurjchem-1645	645	4	zolo[3,4‐c]pyridine	zolo[3,4‐c]pyridine	PROPN
eurjchem-1645	645	5	derivatives	derivative	NOUN
eurjchem-1645	645	6	(	(	PUNCT
eurjchem-1645	645	7	13a‐h	13a‐h	NOUN
eurjchem-1645	645	8	and	and	CCONJ
eurjchem-1645	645	9	14a‐h	14a‐h	NUM
eurjchem-1645	645	10	)	)	PUNCT
eurjchem-1645	645	11	,	,	PUNCT
eurjchem-1645	645	12	the	the	DET
eurjchem-1645	645	13	ic50	ic50	PROPN
eurjchem-1645	645	14	value	value	NOUN
eurjchem-1645	645	15	ranges	range	VERB
eurjchem-1645	645	16	from	from	ADP
eurjchem-1645	645	17	5.12	5.12	NUM
eurjchem-1645	645	18	to	to	ADP
eurjchem-1645	645	19	38.86	38.86	NUM
eurjchem-1645	645	20	µm	µm	ADP
eurjchem-1645	645	21	all	all	DET
eurjchem-1645	645	22	four	four	NUM
eurjchem-1645	645	23	cell	cell	NOUN
eurjchem-1645	645	24	lines	line	NOUN
eurjchem-1645	645	25	.	.	PUNCT
eurjchem-1645	646	1	for	for	ADP
eurjchem-1645	646	2	cell	cell	NOUN
eurjchem-1645	646	3	line	line	NOUN
eurjchem-1645	646	4	a‐549	a‐549	NOUN
eurjchem-1645	646	5	,	,	PUNCT
eurjchem-1645	646	6	compound	compound	NOUN
eurjchem-1645	646	7	13	13	NUM
eurjchem-1645	646	8	g	g	NOUN
eurjchem-1645	646	9	is	be	AUX
eurjchem-1645	646	10	most	most	ADV
eurjchem-1645	646	11	active	active	ADJ
eurjchem-1645	646	12	with	with	ADP
eurjchem-1645	646	13	ic50	ic50	PROPN
eurjchem-1645	646	14	value	value	NOUN
eurjchem-1645	646	15	of	of	ADP
eurjchem-1645	646	16	5.12	5.12	NUM
eurjchem-1645	646	17	µm	µm	NUM
eurjchem-1645	646	18	;	;	PUNCT
eurjchem-1645	646	19	and	and	CCONJ
eurjchem-1645	646	20	compound	compound	NOUN
eurjchem-1645	646	21	13c	13c	NOUN
eurjchem-1645	646	22	is	be	AUX
eurjchem-1645	646	23	also	also	ADV
eurjchem-1645	646	24	active	active	ADJ
eurjchem-1645	646	25	with	with	ADP
eurjchem-1645	646	26	ic50	ic50	PROPN
eurjchem-1645	646	27	value	value	NOUN
eurjchem-1645	646	28	of	of	ADP
eurjchem-1645	646	29	6.81	6.81	NUM
eurjchem-1645	646	30	µm	µm	NOUN
eurjchem-1645	646	31	along	along	ADV
eurjchem-1645	646	32	with	with	ADP
eurjchem-1645	646	33	compounds	compound	NOUN
eurjchem-1645	646	34	13b	13b	NOUN
eurjchem-1645	646	35	,	,	PUNCT
eurjchem-1645	646	36	13e	13e	NUM
eurjchem-1645	646	37	,	,	PUNCT
eurjchem-1645	646	38	13f	13f	NUM
eurjchem-1645	646	39	,	,	PUNCT
eurjchem-1645	646	40	13h	13h	NOUN
eurjchem-1645	646	41	,	,	PUNCT
eurjchem-1645	646	42	15b	15b	NOUN
eurjchem-1645	646	43	and	and	CCONJ
eurjchem-1645	646	44	15d	15d	NUM
eurjchem-1645	646	45	are	be	AUX
eurjchem-1645	646	46	moderately	moderately	ADV
eurjchem-1645	646	47	active	active	ADJ
eurjchem-1645	646	48	with	with	ADP
eurjchem-1645	646	49	ic50	ic50	PROPN
eurjchem-1645	646	50	value	value	NOUN
eurjchem-1645	646	51	of	of	ADP
eurjchem-1645	646	52	15.81	15.81	NUM
eurjchem-1645	646	53	,	,	PUNCT
eurjchem-1645	646	54	13.86	13.86	NUM
eurjchem-1645	646	55	,	,	PUNCT
eurjchem-1645	646	56	15.72	15.72	NUM
eurjchem-1645	646	57	,	,	PUNCT
eurjchem-1645	646	58	13.25	13.25	NUM
eurjchem-1645	646	59	,	,	PUNCT
eurjchem-1645	646	60	14.13	14.13	NUM
eurjchem-1645	646	61	and	and	CCONJ
eurjchem-1645	646	62	11.72	11.72	NUM
eurjchem-1645	646	63	µm	µm	NOUN
eurjchem-1645	646	64	,	,	PUNCT
eurjchem-1645	646	65	respectively	respectively	ADV
eurjchem-1645	646	66	.	.	PUNCT
eurjchem-1645	647	1	the	the	DET
eurjchem-1645	647	2	com‐	com‐	PROPN
eurjchem-1645	647	3	pounds	pound	NOUN
eurjchem-1645	647	4	13a	13a	NOUN
eurjchem-1645	647	5	,	,	PUNCT
eurjchem-1645	647	6	15c	15c	NOUN
eurjchem-1645	647	7	and	and	CCONJ
eurjchem-1645	647	8	15e	15e	NOUN
eurjchem-1645	647	9	are	be	AUX
eurjchem-1645	647	10	most	most	ADV
eurjchem-1645	647	11	inactive	inactive	ADJ
eurjchem-1645	647	12	compounds	compound	NOUN
eurjchem-1645	647	13	in	in	ADP
eurjchem-1645	647	14	the	the	DET
eurjchem-1645	647	15	series	series	NOUN
eurjchem-1645	647	16	.	.	PUNCT
eurjchem-1645	648	1	for	for	ADP
eurjchem-1645	648	2	cell	cell	NOUN
eurjchem-1645	648	3	line	line	NOUN
eurjchem-1645	648	4	hela	hela	PROPN
eurjchem-1645	648	5	,	,	PUNCT
eurjchem-1645	648	6	it	it	PRON
eurjchem-1645	648	7	’s	’	VERB
eurjchem-1645	648	8	have	have	AUX
eurjchem-1645	648	9	ic50	ic50	PROPN
eurjchem-1645	648	10	values	value	NOUN
eurjchem-1645	648	11	are	be	AUX
eurjchem-1645	648	12	in	in	ADP
eurjchem-1645	648	13	between	between	ADP
eurjchem-1645	648	14	8.59	8.59	NUM
eurjchem-1645	648	15	to	to	ADP
eurjchem-1645	648	16	26.87	26.87	NUM
eurjchem-1645	648	17	µm	µm	NOUN
eurjchem-1645	648	18	.	.	PUNCT
eurjchem-1645	649	1	the	the	DET
eurjchem-1645	649	2	compounds	compound	NOUN
eurjchem-1645	649	3	15	15	NUM
eurjchem-1645	649	4	g	g	NOUN
eurjchem-1645	649	5	is	be	AUX
eurjchem-1645	649	6	most	most	ADV
eurjchem-1645	649	7	active	active	ADJ
eurjchem-1645	649	8	with	with	ADP
eurjchem-1645	649	9	ic50	ic50	PROPN
eurjchem-1645	649	10	value	value	NOUN
eurjchem-1645	649	11	of	of	ADP
eurjchem-1645	649	12	8.59	8.59	NUM
eurjchem-1645	649	13	µm	µm	NOUN
eurjchem-1645	649	14	along	along	ADP
eurjchem-1645	649	15	with	with	ADP
eurjchem-1645	649	16	compound	compound	NOUN
eurjchem-1645	649	17	15d	15d	NOUN
eurjchem-1645	649	18	and	and	CCONJ
eurjchem-1645	649	19	13	13	NUM
eurjchem-1645	649	20	g	g	NOUN
eurjchem-1645	649	21	with	with	ADP
eurjchem-1645	649	22	ic50	ic50	PROPN
eurjchem-1645	649	23	values	value	NOUN
eurjchem-1645	649	24	of	of	ADP
eurjchem-1645	649	25	8.87	8.87	NUM
eurjchem-1645	649	26	and	and	CCONJ
eurjchem-1645	649	27	9.12	9.12	NUM
eurjchem-1645	649	28	µm	µm	NOUN
eurjchem-1645	649	29	,	,	PUNCT
eurjchem-1645	649	30	respectively	respectively	ADV
eurjchem-1645	649	31	.	.	PUNCT
eurjchem-1645	650	1	the	the	DET
eurjchem-1645	650	2	compounds	compound	NOUN
eurjchem-1645	650	3	13b	13b	NOUN
eurjchem-1645	650	4	,	,	PUNCT
eurjchem-1645	650	5	13c	13c	NOUN
eurjchem-1645	650	6	,	,	PUNCT
eurjchem-1645	650	7	15a	15a	NOUN
eurjchem-1645	650	8	,	,	PUNCT
eurjchem-1645	650	9	15c	15c	NOUN
eurjchem-1645	650	10	and	and	CCONJ
eurjchem-1645	650	11	15h	15h	NOUN
eurjchem-1645	650	12	are	be	AUX
eurjchem-1645	650	13	moderately	moderately	ADV
eurjchem-1645	650	14	active	active	ADJ
eurjchem-1645	650	15	with	with	ADP
eurjchem-1645	650	16	ic50	ic50	PROPN
eurjchem-1645	650	17	values	value	NOUN
eurjchem-1645	650	18	ranging	range	VERB
eurjchem-1645	650	19	in	in	ADP
eurjchem-1645	650	20	between	between	ADP
eurjchem-1645	650	21	11.32	11.32	NUM
eurjchem-1645	650	22	to	to	ADP
eurjchem-1645	650	23	14.38	14.38	NUM
eurjchem-1645	650	24	µm	µm	NOUN
eurjchem-1645	650	25	.	.	PUNCT
eurjchem-1645	651	1	remaining	remain	VERB
eurjchem-1645	651	2	compounds	compound	NOUN
eurjchem-1645	651	3	are	be	AUX
eurjchem-1645	651	4	less	less	ADV
eurjchem-1645	651	5	active	active	ADJ
eurjchem-1645	651	6	with	with	ADP
eurjchem-1645	651	7	ic50	ic50	PROPN
eurjchem-1645	651	8	value	value	NOUN
eurjchem-1645	651	9	in	in	ADP
eurjchem-1645	651	10	between	between	ADP
eurjchem-1645	651	11	15.16	15.16	NUM
eurjchem-1645	651	12	to	to	ADP
eurjchem-1645	651	13	26.87	26.87	NUM
eurjchem-1645	651	14	µm	µm	NOUN
eurjchem-1645	651	15	.	.	PUNCT
eurjchem-1645	652	1	for	for	ADP
eurjchem-1645	652	2	cell	cell	NOUN
eurjchem-1645	652	3	line	line	NOUN
eurjchem-1645	652	4	mcf‐7	mcf‐7	PROPN
eurjchem-1645	652	5	,	,	PUNCT
eurjchem-1645	652	6	the	the	DET
eurjchem-1645	652	7	ic50	ic50	PROPN
eurjchem-1645	652	8	values	value	NOUN
eurjchem-1645	652	9	are	be	AUX
eurjchem-1645	652	10	in	in	ADP
eurjchem-1645	652	11	the	the	DET
eurjchem-1645	652	12	range	range	NOUN
eurjchem-1645	652	13	of	of	ADP
eurjchem-1645	652	14	6.12	6.12	NUM
eurjchem-1645	652	15	and	and	CCONJ
eurjchem-1645	652	16	26.32	26.32	NUM
eurjchem-1645	652	17	µm	µm	NOUN
eurjchem-1645	652	18	.	.	PUNCT
eurjchem-1645	653	1	the	the	DET
eurjchem-1645	653	2	compounds	compound	NOUN
eurjchem-1645	653	3	15h	15h	NUM
eurjchem-1645	653	4	,	,	PUNCT
eurjchem-1645	653	5	15	15	NUM
eurjchem-1645	653	6	g	g	NOUN
eurjchem-1645	653	7	and	and	CCONJ
eurjchem-1645	653	8	13	13	NUM
eurjchem-1645	653	9	g	g	NOUN
eurjchem-1645	653	10	are	be	AUX
eurjchem-1645	653	11	most	most	ADV
eurjchem-1645	653	12	active	active	ADJ
eurjchem-1645	653	13	ic50	ic50	PROPN
eurjchem-1645	653	14	values	value	NOUN
eurjchem-1645	653	15	of	of	ADP
eurjchem-1645	653	16	6.12	6.12	NUM
eurjchem-1645	653	17	,	,	PUNCT
eurjchem-1645	653	18	8.63	8.63	NUM
eurjchem-1645	653	19	and	and	CCONJ
eurjchem-1645	653	20	9.36	9.36	NUM
eurjchem-1645	653	21	µm	µm	NOUN
eurjchem-1645	653	22	,	,	PUNCT
eurjchem-1645	653	23	respectively	respectively	ADV
eurjchem-1645	653	24	,	,	PUNCT
eurjchem-1645	653	25	total	total	ADJ
eurjchem-1645	653	26	five	five	NUM
eurjchem-1645	653	27	compounds	compound	NOUN
eurjchem-1645	653	28	are	be	AUX
eurjchem-1645	653	29	moderately	moderately	ADV
eurjchem-1645	653	30	active	active	ADJ
eurjchem-1645	653	31	with	with	ADP
eurjchem-1645	653	32	ic50	ic50	PROPN
eurjchem-1645	653	33	values	value	NOUN
eurjchem-1645	653	34	in	in	ADP
eurjchem-1645	653	35	the	the	DET
eurjchem-1645	653	36	range	range	NOUN
eurjchem-1645	653	37	of	of	ADP
eurjchem-1645	653	38	11.36	11.36	NUM
eurjchem-1645	653	39	to	to	ADP
eurjchem-1645	653	40	14.82	14.82	NUM
eurjchem-1645	653	41	µm	µm	ADP
eurjchem-1645	653	42	and	and	CCONJ
eurjchem-1645	653	43	eight	eight	NUM
eurjchem-1645	653	44	compounds	compound	NOUN
eurjchem-1645	653	45	are	be	AUX
eurjchem-1645	653	46	less	less	ADV
eurjchem-1645	653	47	active	active	ADJ
eurjchem-1645	653	48	with	with	ADP
eurjchem-1645	653	49	ic50	ic50	PROPN
eurjchem-1645	653	50	values	value	NOUN
eurjchem-1645	653	51	are	be	AUX
eurjchem-1645	653	52	in	in	ADP
eurjchem-1645	653	53	the	the	DET
eurjchem-1645	653	54	range	range	NOUN
eurjchem-1645	653	55	of	of	ADP
eurjchem-1645	653	56	16.12	16.12	NUM
eurjchem-1645	653	57	to	to	ADP
eurjchem-1645	653	58	26.32	26.32	NUM
eurjchem-1645	653	59	µm	µm	NOUN
eurjchem-1645	653	60	.	.	PUNCT
eurjchem-1645	654	1	for	for	ADP
eurjchem-1645	654	2	cell	cell	NOUN
eurjchem-1645	654	3	line	line	NOUN
eurjchem-1645	654	4	du‐145	du‐145	PROPN
eurjchem-1645	654	5	,	,	PUNCT
eurjchem-1645	654	6	the	the	DET
eurjchem-1645	654	7	ic50	ic50	PROPN
eurjchem-1645	654	8	value	value	NOUN
eurjchem-1645	654	9	ranges	range	VERB
eurjchem-1645	654	10	from	from	ADP
eurjchem-1645	654	11	9.52	9.52	NUM
eurjchem-1645	654	12	to	to	ADP
eurjchem-1645	654	13	38.56	38.56	NUM
eurjchem-1645	654	14	µm	µm	NOUN
eurjchem-1645	654	15	.	.	PUNCT
eurjchem-1645	655	1	the	the	DET
eurjchem-1645	655	2	compounds	compound	NOUN
eurjchem-1645	655	3	15a	15a	NOUN
eurjchem-1645	655	4	is	be	AUX
eurjchem-1645	655	5	most	most	ADV
eurjchem-1645	655	6	active	active	ADJ
eurjchem-1645	655	7	with	with	ADP
eurjchem-1645	655	8	ic50	ic50	PROPN
eurjchem-1645	655	9	value	value	NOUN
eurjchem-1645	655	10	of	of	ADP
eurjchem-1645	655	11	9.52	9.52	NUM
eurjchem-1645	655	12	µm	µm	NOUN
eurjchem-1645	655	13	along	along	ADP
eurjchem-1645	655	14	with	with	ADP
eurjchem-1645	655	15	compound	compound	NOUN
eurjchem-1645	655	16	13c	13c	NOUN
eurjchem-1645	655	17	having	have	VERB
eurjchem-1645	655	18	ic50	ic50	PROPN
eurjchem-1645	655	19	value	value	NOUN
eurjchem-1645	655	20	of	of	ADP
eurjchem-1645	655	21	10.37	10.37	NUM
eurjchem-1645	655	22	µm	µm	NUM
eurjchem-1645	655	23	are	be	AUX
eurjchem-1645	655	24	most	most	ADV
eurjchem-1645	655	25	active	active	ADJ
eurjchem-1645	655	26	.	.	PUNCT
eurjchem-1645	656	1	the	the	DET
eurjchem-1645	656	2	compounds	compound	NOUN
eurjchem-1645	656	3	13e	13e	NUM
eurjchem-1645	656	4	,	,	PUNCT
eurjchem-1645	656	5	13h	13h	NOUN
eurjchem-1645	656	6	,	,	PUNCT
eurjchem-1645	656	7	15b	15b	NOUN
eurjchem-1645	656	8	,	,	PUNCT
eurjchem-1645	656	9	15c	15c	NOUN
eurjchem-1645	656	10	,	,	PUNCT
eurjchem-1645	656	11	15d	15d	NUM
eurjchem-1645	656	12	,	,	PUNCT
eurjchem-1645	656	13	15h	15h	NOUN
eurjchem-1645	656	14	and	and	CCONJ
eurjchem-1645	656	15	15e	15e	NOUN
eurjchem-1645	656	16	are	be	AUX
eurjchem-1645	656	17	also	also	ADV
eurjchem-1645	656	18	active	active	ADJ
eurjchem-1645	656	19	compounds	compound	NOUN
eurjchem-1645	656	20	in	in	ADP
eurjchem-1645	656	21	du‐145	du‐145	NOUN
eurjchem-1645	656	22	cell	cell	NOUN
eurjchem-1645	656	23	line	line	NOUN
eurjchem-1645	656	24	with	with	ADP
eurjchem-1645	656	25	ic50	ic50	PROPN
eurjchem-1645	656	26	values	value	NOUN
eurjchem-1645	656	27	in	in	ADP
eurjchem-1645	656	28	the	the	DET
eurjchem-1645	656	29	range	range	NOUN
eurjchem-1645	656	30	of	of	ADP
eurjchem-1645	656	31	10‐12	10‐12	NUM
eurjchem-1645	656	32	µm	µm	ADP
eurjchem-1645	656	33	total	total	ADJ
eurjchem-1645	656	34	seven	seven	NUM
eurjchem-1645	656	35	compounds	compound	NOUN
eurjchem-1645	656	36	are	be	AUX
eurjchem-1645	656	37	less	less	ADV
eurjchem-1645	656	38	active	active	ADJ
eurjchem-1645	656	39	with	with	ADP
eurjchem-1645	656	40	ic50	ic50	PROPN
eurjchem-1645	656	41	values	value	NOUN
eurjchem-1645	656	42	in	in	ADP
eurjchem-1645	656	43	the	the	DET
eurjchem-1645	656	44	range	range	NOUN
eurjchem-1645	656	45	of	of	ADP
eurjchem-1645	656	46	13.52	13.52	NUM
eurjchem-1645	656	47	to	to	ADP
eurjchem-1645	656	48	38.56	38.56	NUM
eurjchem-1645	656	49	µm	µm	NOUN
eurjchem-1645	656	50	.	.	PUNCT
eurjchem-1645	657	1	compound	compound	NOUN
eurjchem-1645	657	2	13a	13a	NOUN
eurjchem-1645	657	3	having	have	VERB
eurjchem-1645	657	4	3‐methoxy	3‐methoxy	ADJ
eurjchem-1645	657	5	phenyl	phenyl	NOUN
eurjchem-1645	657	6	and	and	CCONJ
eurjchem-1645	657	7	benzofuran‐	benzofuran‐	NOUN
eurjchem-1645	657	8	2‐yl	2‐yl	NUM
eurjchem-1645	657	9	groups	group	NOUN
eurjchem-1645	657	10	is	be	AUX
eurjchem-1645	657	11	inactive	inactive	ADJ
eurjchem-1645	657	12	compared	compare	VERB
eurjchem-1645	657	13	with	with	ADP
eurjchem-1645	657	14	standard	standard	NOUN
eurjchem-1645	657	15	with	with	ADP
eurjchem-1645	657	16	ic50	ic50	PROPN
eurjchem-1645	657	17	values	value	NOUN
eurjchem-1645	657	18	in	in	ADP
eurjchem-1645	657	19	the	the	DET
eurjchem-1645	657	20	range	range	NOUN
eurjchem-1645	657	21	of	of	ADP
eurjchem-1645	657	22	22.72	22.72	NUM
eurjchem-1645	657	23	to	to	ADP
eurjchem-1645	657	24	28.87	28.87	NUM
eurjchem-1645	657	25	µm	µm	NOUN
eurjchem-1645	657	26	in	in	ADP
eurjchem-1645	657	27	all	all	DET
eurjchem-1645	657	28	cell	cell	NOUN
eurjchem-1645	657	29	lines	line	NOUN
eurjchem-1645	657	30	.	.	PUNCT
eurjchem-1645	658	1	compound	compound	NOUN
eurjchem-1645	658	2	13b	13b	X
eurjchem-1645	658	3	is	be	AUX
eurjchem-1645	658	4	moderately	moderately	ADV
eurjchem-1645	658	5	active	active	ADJ
eurjchem-1645	658	6	with	with	ADP
eurjchem-1645	658	7	ic50	ic50	PROPN
eurjchem-1645	658	8	value	value	NOUN
eurjchem-1645	658	9	of	of	ADP
eurjchem-1645	658	10	14.33	14.33	NUM
eurjchem-1645	658	11	µm	µm	NOUN
eurjchem-1645	658	12	of	of	ADP
eurjchem-1645	658	13	hela	hela	PROPN
eurjchem-1645	658	14	cell	cell	NOUN
eurjchem-1645	658	15	line	line	NOUN
eurjchem-1645	658	16	and	and	CCONJ
eurjchem-1645	658	17	in	in	ADP
eurjchem-1645	658	18	remaining	remain	VERB
eurjchem-1645	658	19	all	all	DET
eurjchem-1645	658	20	cell	cell	NOUN
eurjchem-1645	658	21	lines	line	NOUN
eurjchem-1645	658	22	it	it	PRON
eurjchem-1645	658	23	is	be	AUX
eurjchem-1645	658	24	inactive	inactive	ADJ
eurjchem-1645	658	25	.	.	PUNCT
eurjchem-1645	659	1	the	the	DET
eurjchem-1645	659	2	compound	compound	NOUN
eurjchem-1645	659	3	13c	13c	NOUN
eurjchem-1645	659	4	is	be	AUX
eurjchem-1645	659	5	active	active	ADJ
eurjchem-1645	659	6	in	in	ADP
eurjchem-1645	659	7	a‐549	a‐549	NOUN
eurjchem-1645	659	8	cell	cell	NOUN
eurjchem-1645	659	9	line	line	NOUN
eurjchem-1645	659	10	and	and	CCONJ
eurjchem-1645	659	11	du‐145	du‐145	NOUN
eurjchem-1645	659	12	and	and	CCONJ
eurjchem-1645	659	13	is	be	AUX
eurjchem-1645	659	14	moderately	moderately	ADV
eurjchem-1645	659	15	active	active	ADJ
eurjchem-1645	659	16	in	in	ADP
eurjchem-1645	659	17	hela	hela	PROPN
eurjchem-1645	659	18	and	and	CCONJ
eurjchem-1645	659	19	it	it	PRON
eurjchem-1645	659	20	is	be	AUX
eurjchem-1645	659	21	most	most	ADV
eurjchem-1645	659	22	inactive	inactive	ADJ
eurjchem-1645	659	23	in	in	ADP
eurjchem-1645	659	24	mcf‐7	mcf‐7	NOUN
eurjchem-1645	659	25	due	due	ADP
eurjchem-1645	659	26	to	to	ADP
eurjchem-1645	659	27	presence	presence	NOUN
eurjchem-1645	659	28	of	of	ADP
eurjchem-1645	659	29	3‐methoxy	3‐methoxy	ADJ
eurjchem-1645	659	30	phenyl	phenyl	NOUN
eurjchem-1645	659	31	and	and	CCONJ
eurjchem-1645	659	32	3‐yl	3‐yl	NUM
eurjchem-1645	659	33	quinolone	quinolone	NOUN
eurjchem-1645	659	34	groups	group	NOUN
eurjchem-1645	659	35	.	.	PUNCT
eurjchem-1645	660	1	the	the	DET
eurjchem-1645	660	2	compound	compound	NOUN
eurjchem-1645	660	3	13d	13d	NOUN
eurjchem-1645	660	4	is	be	AUX
eurjchem-1645	660	5	moderately	moderately	ADV
eurjchem-1645	660	6	active	active	ADJ
eurjchem-1645	660	7	in	in	ADP
eurjchem-1645	660	8	a‐549	a‐549	NOUN
eurjchem-1645	660	9	and	and	CCONJ
eurjchem-1645	660	10	in	in	ADP
eurjchem-1645	660	11	remaining	remain	VERB
eurjchem-1645	660	12	cell	cell	NOUN
eurjchem-1645	660	13	lines	line	NOUN
eurjchem-1645	660	14	,	,	PUNCT
eurjchem-1645	660	15	it	it	PRON
eurjchem-1645	660	16	is	be	AUX
eurjchem-1645	660	17	inactive	inactive	ADJ
eurjchem-1645	660	18	.	.	PUNCT
eurjchem-1645	661	1	compound	compound	NOUN
eurjchem-1645	661	2	13e	13e	NOUN
eurjchem-1645	661	3	is	be	AUX
eurjchem-1645	661	4	inactive	inactive	ADJ
eurjchem-1645	661	5	in	in	ADP
eurjchem-1645	661	6	cell	cell	NOUN
eurjchem-1645	661	7	lines	line	NOUN
eurjchem-1645	661	8	hela	hela	ADJ
eurjchem-1645	661	9	and	and	CCONJ
eurjchem-1645	661	10	in	in	ADP
eurjchem-1645	661	11	remaining	remain	VERB
eurjchem-1645	661	12	cell	cell	NOUN
eurjchem-1645	661	13	lines	line	NOUN
eurjchem-1645	661	14	,	,	PUNCT
eurjchem-1645	661	15	it	it	PRON
eurjchem-1645	661	16	is	be	AUX
eurjchem-1645	661	17	moderately	moderately	ADV
eurjchem-1645	661	18	active	active	ADJ
eurjchem-1645	661	19	with	with	ADP
eurjchem-1645	661	20	ic50	ic50	PROPN
eurjchem-1645	661	21	values	value	VERB
eurjchem-1645	661	22	11.82	11.82	NUM
eurjchem-1645	661	23	to	to	ADP
eurjchem-1645	661	24	13.86	13.86	NUM
eurjchem-1645	661	25	µm	µm	NOUN
eurjchem-1645	661	26	,	,	PUNCT
eurjchem-1645	661	27	its	its	PRON
eurjchem-1645	661	28	having	have	VERB
eurjchem-1645	661	29	pyrimidine	pyrimidine	NOUN
eurjchem-1645	661	30	and	and	CCONJ
eurjchem-1645	661	31	benzo‐furan	benzo‐furan	ADJ
eurjchem-1645	661	32	group	group	NOUN
eurjchem-1645	661	33	.	.	PUNCT
eurjchem-1645	662	1	compound	compound	NOUN
eurjchem-1645	662	2	13f	13f	NOUN
eurjchem-1645	662	3	is	be	AUX
eurjchem-1645	662	4	mostly	mostly	ADV
eurjchem-1645	662	5	inactive	inactive	ADJ
eurjchem-1645	662	6	in	in	ADP
eurjchem-1645	662	7	all	all	DET
eurjchem-1645	662	8	cell	cell	NOUN
eurjchem-1645	662	9	lines	line	NOUN
eurjchem-1645	662	10	because	because	SCONJ
eurjchem-1645	662	11	the	the	DET
eurjchem-1645	662	12	presence	presence	NOUN
eurjchem-1645	662	13	of	of	ADP
eurjchem-1645	662	14	pyrimidine	pyrimidine	NOUN
eurjchem-1645	662	15	and	and	CCONJ
eurjchem-1645	662	16	benzo‐thiophene	benzo‐thiophene	NOUN
eurjchem-1645	662	17	group	group	NOUN
eurjchem-1645	662	18	.	.	PUNCT
eurjchem-1645	663	1	the	the	DET
eurjchem-1645	663	2	compound	compound	NOUN
eurjchem-1645	663	3	13	13	NUM
eurjchem-1645	663	4	g	g	NOUN
eurjchem-1645	663	5	is	be	AUX
eurjchem-1645	663	6	active	active	ADJ
eurjchem-1645	663	7	com‐	com‐	PRON
eurjchem-1645	663	8	pound	pound	NOUN
eurjchem-1645	663	9	in	in	ADP
eurjchem-1645	663	10	all	all	DET
eurjchem-1645	663	11	cell	cell	NOUN
eurjchem-1645	663	12	lines	line	NOUN
eurjchem-1645	663	13	with	with	ADP
eurjchem-1645	663	14	ic50	ic50	PROPN
eurjchem-1645	663	15	values	value	NOUN
eurjchem-1645	663	16	in	in	ADP
eurjchem-1645	663	17	the	the	DET
eurjchem-1645	663	18	range	range	NOUN
eurjchem-1645	663	19	of	of	ADP
eurjchem-1645	663	20	5.12	5.12	NUM
eurjchem-1645	663	21	to	to	ADP
eurjchem-1645	663	22	9.36	9.36	NUM
eurjchem-1645	663	23	µm	µm	ADP
eurjchem-1645	663	24	and	and	CCONJ
eurjchem-1645	663	25	for	for	ADP
eurjchem-1645	663	26	du‐145	du‐145	PROPN
eurjchem-1645	663	27	,	,	PUNCT
eurjchem-1645	663	28	it	it	PRON
eurjchem-1645	663	29	is	be	AUX
eurjchem-1645	663	30	moderately	moderately	ADV
eurjchem-1645	663	31	active	active	ADJ
eurjchem-1645	663	32	with	with	ADP
eurjchem-1645	663	33	ic50	ic50	PROPN
eurjchem-1645	663	34	values	value	NOUN
eurjchem-1645	663	35	of	of	ADP
eurjchem-1645	663	36	13.52	13.52	NUM
eurjchem-1645	663	37	µm	µm	NOUN
eurjchem-1645	663	38	due	due	ADP
eurjchem-1645	663	39	to	to	ADP
eurjchem-1645	663	40	the	the	DET
eurjchem-1645	663	41	presence	presence	NOUN
eurjchem-1645	663	42	of	of	ADP
eurjchem-1645	663	43	pyrimidine	pyrimidine	NOUN
eurjchem-1645	663	44	and	and	CCONJ
eurjchem-1645	663	45	3‐yl	3‐yl	NUM
eurjchem-1645	663	46	quinolone	quinolone	NOUN
eurjchem-1645	663	47	group	group	NOUN
eurjchem-1645	663	48	.	.	PUNCT
eurjchem-1645	664	1	compound	compound	NOUN
eurjchem-1645	664	2	13h	13h	PROPN
eurjchem-1645	664	3	,	,	PUNCT
eurjchem-1645	664	4	for	for	ADP
eurjchem-1645	664	5	hela	hela	ADJ
eurjchem-1645	664	6	cell	cell	NOUN
eurjchem-1645	664	7	line	line	NOUN
eurjchem-1645	664	8	,	,	PUNCT
eurjchem-1645	664	9	is	be	AUX
eurjchem-1645	664	10	inactive	inactive	ADJ
eurjchem-1645	664	11	with	with	ADP
eurjchem-1645	664	12	ic50	ic50	PROPN
eurjchem-1645	664	13	value	value	NOUN
eurjchem-1645	664	14	of	of	ADP
eurjchem-1645	664	15	17.78	17.78	NUM
eurjchem-1645	664	16	µm	µm	NOUN
eurjchem-1645	664	17	and	and	CCONJ
eurjchem-1645	664	18	,	,	PUNCT
eurjchem-1645	664	19	for	for	ADP
eurjchem-1645	664	20	remaining	remain	VERB
eurjchem-1645	664	21	cell	cell	NOUN
eurjchem-1645	664	22	lines	line	NOUN
eurjchem-1645	664	23	,	,	PUNCT
eurjchem-1645	664	24	it	it	PRON
eurjchem-1645	664	25	is	be	AUX
eurjchem-1645	664	26	moderately	moderately	ADV
eurjchem-1645	664	27	active	active	ADJ
eurjchem-1645	664	28	with	with	ADP
eurjchem-1645	664	29	ic50	ic50	PROPN
eurjchem-1645	664	30	values	value	NOUN
eurjchem-1645	664	31	in	in	ADP
eurjchem-1645	664	32	the	the	DET
eurjchem-1645	664	33	range	range	NOUN
eurjchem-1645	664	34	of	of	ADP
eurjchem-1645	664	35	11.72	11.72	NUM
eurjchem-1645	664	36	to	to	ADP
eurjchem-1645	664	37	13.82	13.82	NUM
eurjchem-1645	664	38	µm	µm	ADP
eurjchem-1645	664	39	due	due	ADP
eurjchem-1645	664	40	to	to	ADP
eurjchem-1645	664	41	presence	presence	NOUN
eurjchem-1645	664	42	of	of	ADP
eurjchem-1645	664	43	pyrimidine	pyrimidine	NOUN
eurjchem-1645	664	44	and	and	CCONJ
eurjchem-1645	664	45	5‐yl‐quinolone	5‐yl‐quinolone	NUM
eurjchem-1645	664	46	group	group	NOUN
eurjchem-1645	664	47	.	.	PUNCT
eurjchem-1645	665	1	the	the	DET
eurjchem-1645	665	2	compound	compound	NOUN
eurjchem-1645	665	3	15a	15a	NOUN
eurjchem-1645	665	4	having	have	VERB
eurjchem-1645	665	5	3‐methoxy	3‐methoxy	ADJ
eurjchem-1645	665	6	phenyl	phenyl	NOUN
eurjchem-1645	665	7	and	and	CCONJ
eurjchem-1645	665	8	benzofuran‐2‐yl	benzofuran‐2‐yl	NOUN
eurjchem-1645	665	9	groups	group	NOUN
eurjchem-1645	665	10	are	be	AUX
eurjchem-1645	665	11	mostly	mostly	ADV
eurjchem-1645	665	12	active	active	ADJ
eurjchem-1645	665	13	in	in	ADP
eurjchem-1645	665	14	all	all	DET
eurjchem-1645	665	15	cell	cell	NOUN
eurjchem-1645	665	16	lines	line	NOUN
eurjchem-1645	665	17	with	with	ADP
eurjchem-1645	665	18	ic50	ic50	PROPN
eurjchem-1645	665	19	values	value	NOUN
eurjchem-1645	665	20	in	in	ADP
eurjchem-1645	665	21	the	the	DET
eurjchem-1645	665	22	range	range	NOUN
eurjchem-1645	665	23	of	of	ADP
eurjchem-1645	665	24	10.82	10.82	NUM
eurjchem-1645	665	25	to	to	ADP
eurjchem-1645	665	26	13.39	13.39	NUM
eurjchem-1645	665	27	µm	µm	NUM
eurjchem-1645	665	28	and	and	CCONJ
eurjchem-1645	665	29	is	be	AUX
eurjchem-1645	665	30	active	active	ADJ
eurjchem-1645	665	31	in	in	ADP
eurjchem-1645	665	32	du‐145	du‐145	NOUN
eurjchem-1645	665	33	with	with	ADP
eurjchem-1645	665	34	ic50	ic50	PROPN
eurjchem-1645	665	35	value	value	NOUN
eurjchem-1645	665	36	of	of	ADP
eurjchem-1645	665	37	9.52	9.52	NUM
eurjchem-1645	665	38	µm	µm	NOUN
eurjchem-1645	665	39	.	.	PUNCT
eurjchem-1645	666	1	the	the	DET
eurjchem-1645	666	2	compound	compound	NOUN
eurjchem-1645	666	3	15b	15b	X
eurjchem-1645	666	4	is	be	AUX
eurjchem-1645	666	5	moderately	moderately	ADV
eurjchem-1645	666	6	active	active	ADJ
eurjchem-1645	666	7	in	in	ADP
eurjchem-1645	666	8	a‐549	a‐549	NOUN
eurjchem-1645	666	9	and	and	CCONJ
eurjchem-1645	666	10	du‐145	du‐145	NOUN
eurjchem-1645	666	11	cell	cell	NOUN
eurjchem-1645	666	12	lines	line	NOUN
eurjchem-1645	667	1	and	and	CCONJ
eurjchem-1645	667	2	it	it	PRON
eurjchem-1645	667	3	is	be	AUX
eurjchem-1645	667	4	inactive	inactive	ADJ
eurjchem-1645	667	5	in	in	ADP
eurjchem-1645	667	6	hela	hela	PROPN
eurjchem-1645	667	7	and	and	CCONJ
eurjchem-1645	667	8	mcf‐7	mcf‐7	NOUN
eurjchem-1645	667	9	cell	cell	NOUN
eurjchem-1645	667	10	line	line	NOUN
eurjchem-1645	667	11	.	.	PUNCT
eurjchem-1645	668	1	the	the	DET
eurjchem-1645	668	2	compound	compound	NOUN
eurjchem-1645	668	3	15c	15c	NOUN
eurjchem-1645	668	4	is	be	AUX
eurjchem-1645	668	5	moderately	moderately	ADV
eurjchem-1645	668	6	active	active	ADJ
eurjchem-1645	668	7	in	in	ADP
eurjchem-1645	668	8	hela	hela	PROPN
eurjchem-1645	668	9	and	and	CCONJ
eurjchem-1645	668	10	du‐145	du‐145	PROPN
eurjchem-1645	668	11	(	(	PUNCT
eurjchem-1645	668	12	ic50	ic50	PROPN
eurjchem-1645	668	13	value	value	NOUN
eurjchem-1645	668	14	of	of	ADP
eurjchem-1645	668	15	11.52	11.52	NUM
eurjchem-1645	668	16	µm	µm	NOUN
eurjchem-1645	668	17	)	)	PUNCT
eurjchem-1645	668	18	cell	cell	NOUN
eurjchem-1645	668	19	lines	line	NOUN
eurjchem-1645	668	20	and	and	CCONJ
eurjchem-1645	668	21	it	it	PRON
eurjchem-1645	668	22	is	be	AUX
eurjchem-1645	668	23	inactive	inactive	ADJ
eurjchem-1645	668	24	in	in	ADP
eurjchem-1645	668	25	a‐549	a‐549	NOUN
eurjchem-1645	668	26	and	and	CCONJ
eurjchem-1645	668	27	mcf‐7	mcf‐7	NOUN
eurjchem-1645	668	28	cell	cell	NOUN
eurjchem-1645	668	29	line	line	NOUN
eurjchem-1645	668	30	23.86	23.86	NUM
eurjchem-1645	668	31	and	and	CCONJ
eurjchem-1645	668	32	20.63	20.63	NUM
eurjchem-1645	668	33	µm	µm	NOUN
eurjchem-1645	668	34	,	,	PUNCT
eurjchem-1645	668	35	respectively	respectively	ADV
eurjchem-1645	668	36	.	.	PUNCT
eurjchem-1645	669	1	the	the	DET
eurjchem-1645	669	2	compound	compound	NOUN
eurjchem-1645	669	3	15d	15d	NUM
eurjchem-1645	669	4	is	be	AUX
eurjchem-1645	669	5	active	active	ADJ
eurjchem-1645	669	6	for	for	ADP
eurjchem-1645	669	7	hela	hela	ADJ
eurjchem-1645	669	8	cell	cell	NOUN
eurjchem-1645	669	9	line	line	NOUN
eurjchem-1645	669	10	with	with	ADP
eurjchem-1645	669	11	ic50	ic50	PROPN
eurjchem-1645	669	12	value	value	NOUN
eurjchem-1645	669	13	of	of	ADP
eurjchem-1645	669	14	8.87	8.87	NUM
eurjchem-1645	669	15	µm	µm	NOUN
eurjchem-1645	669	16	and	and	CCONJ
eurjchem-1645	669	17	it	it	PRON
eurjchem-1645	669	18	is	be	AUX
eurjchem-1645	669	19	also	also	ADV
eurjchem-1645	669	20	moderately	moderately	ADV
eurjchem-1645	669	21	active	active	ADJ
eurjchem-1645	669	22	for	for	ADP
eurjchem-1645	669	23	a‐549	a‐549	NOUN
eurjchem-1645	669	24	with	with	ADP
eurjchem-1645	669	25	ic50	ic50	PROPN
eurjchem-1645	669	26	value	value	NOUN
eurjchem-1645	669	27	of	of	ADP
eurjchem-1645	669	28	11.72	11.72	NUM
eurjchem-1645	669	29	µm	µm	NOUN
eurjchem-1645	669	30	,	,	PUNCT
eurjchem-1645	669	31	for	for	ADP
eurjchem-1645	669	32	mcf‐7	mcf‐7	NOUN
eurjchem-1645	669	33	cell	cell	NOUN
eurjchem-1645	669	34	line	line	NOUN
eurjchem-1645	669	35	with	with	ADP
eurjchem-1645	669	36	ic50	ic50	PROPN
eurjchem-1645	669	37	value	value	NOUN
eurjchem-1645	669	38	of	of	ADP
eurjchem-1645	669	39	13.12	13.12	NUM
eurjchem-1645	669	40	µm	µm	NOUN
eurjchem-1645	669	41	with	with	ADP
eurjchem-1645	669	42	moderate	moderate	ADJ
eurjchem-1645	669	43	active	active	ADJ
eurjchem-1645	669	44	interestingly	interestingly	ADV
eurjchem-1645	669	45	it	it	PRON
eurjchem-1645	669	46	is	be	AUX
eurjchem-1645	669	47	in	in	ADP
eurjchem-1645	669	48	active	active	ADJ
eurjchem-1645	669	49	for	for	ADP
eurjchem-1645	669	50	du‐145	du‐145	NOUN
eurjchem-1645	669	51	cell	cell	NOUN
eurjchem-1645	669	52	line	line	NOUN
eurjchem-1645	669	53	with	with	ADP
eurjchem-1645	669	54	ic50	ic50	PROPN
eurjchem-1645	669	55	value	value	NOUN
eurjchem-1645	669	56	of	of	ADP
eurjchem-1645	669	57	18.86	18.86	NUM
eurjchem-1645	669	58	µm	µm	NOUN
eurjchem-1645	669	59	.	.	PUNCT
eurjchem-1645	670	1	the	the	DET
eurjchem-1645	670	2	compound	compound	NOUN
eurjchem-1645	670	3	15e	15e	PROPN
eurjchem-1645	670	4	having	have	VERB
eurjchem-1645	670	5	pyrimidine	pyrimidine	NOUN
eurjchem-1645	670	6	and	and	CCONJ
eurjchem-1645	670	7	benzo‐furan	benzo‐furan	ADJ
eurjchem-1645	670	8	group	group	NOUN
eurjchem-1645	670	9	is	be	AUX
eurjchem-1645	670	10	moderately	moderately	ADV
eurjchem-1645	670	11	active	active	ADJ
eurjchem-1645	670	12	for	for	ADP
eurjchem-1645	670	13	du‐145	du‐145	NOUN
eurjchem-1645	670	14	cell	cell	NOUN
eurjchem-1645	670	15	line	line	NOUN
eurjchem-1645	670	16	with	with	ADP
eurjchem-1645	670	17	ic50	ic50	PROPN
eurjchem-1645	670	18	value	value	NOUN
eurjchem-1645	670	19	of	of	ADP
eurjchem-1645	670	20	12.52	12.52	NUM
eurjchem-1645	670	21	µm	µm	NOUN
eurjchem-1645	670	22	and	and	CCONJ
eurjchem-1645	670	23	for	for	ADP
eurjchem-1645	670	24	remaining	remain	VERB
eurjchem-1645	670	25	cell	cell	NOUN
eurjchem-1645	670	26	lines	line	NOUN
eurjchem-1645	670	27	,	,	PUNCT
eurjchem-1645	670	28	it	it	PRON
eurjchem-1645	670	29	is	be	AUX
eurjchem-1645	670	30	inactive	inactive	ADJ
eurjchem-1645	670	31	.	.	PUNCT
eurjchem-1645	671	1	the	the	DET
eurjchem-1645	671	2	compound	compound	NOUN
eurjchem-1645	671	3	15f	15f	PROPN
eurjchem-1645	671	4	having	have	VERB
eurjchem-1645	671	5	ic50	ic50	PROPN
eurjchem-1645	671	6	values	value	NOUN
eurjchem-1645	671	7	of	of	ADP
eurjchem-1645	671	8	10.78	10.78	NUM
eurjchem-1645	671	9	µm	µm	NOUN
eurjchem-1645	671	10	is	be	AUX
eurjchem-1645	671	11	active	active	ADJ
eurjchem-1645	671	12	for	for	ADP
eurjchem-1645	671	13	a‐549	a‐549	NOUN
eurjchem-1645	671	14	cell	cell	NOUN
eurjchem-1645	671	15	line	line	NOUN
eurjchem-1645	671	16	and	and	CCONJ
eurjchem-1645	671	17	it	it	PRON
eurjchem-1645	671	18	is	be	AUX
eurjchem-1645	671	19	inactive	inactive	ADJ
eurjchem-1645	671	20	for	for	ADP
eurjchem-1645	671	21	remaining	remain	VERB
eurjchem-1645	671	22	all	all	DET
eurjchem-1645	671	23	cell	cell	NOUN
eurjchem-1645	671	24	lines	line	NOUN
eurjchem-1645	671	25	with	with	ADP
eurjchem-1645	671	26	ic50	ic50	PROPN
eurjchem-1645	671	27	values	value	NOUN
eurjchem-1645	671	28	of	of	ADP
eurjchem-1645	671	29	14.82	14.82	NUM
eurjchem-1645	671	30	to	to	ADP
eurjchem-1645	671	31	18.78	18.78	NUM
eurjchem-1645	671	32	µm	µm	NOUN
eurjchem-1645	671	33	.	.	PUNCT
eurjchem-1645	672	1	the	the	DET
eurjchem-1645	672	2	compound	compound	NOUN
eurjchem-1645	672	3	15	15	NUM
eurjchem-1645	672	4	g	g	NOUN
eurjchem-1645	672	5	is	be	AUX
eurjchem-1645	672	6	active	active	ADJ
eurjchem-1645	672	7	for	for	ADP
eurjchem-1645	672	8	a‐549	a‐549	NOUN
eurjchem-1645	672	9	,	,	PUNCT
eurjchem-1645	672	10	hela	hela	PROPN
eurjchem-1645	672	11	and	and	CCONJ
eurjchem-1645	672	12	mcf‐7	mcf‐7	NOUN
eurjchem-1645	672	13	cell	cell	NOUN
eurjchem-1645	672	14	lines	line	NOUN
eurjchem-1645	672	15	with	with	ADP
eurjchem-1645	672	16	ic50	ic50	PROPN
eurjchem-1645	672	17	values	value	NOUN
eurjchem-1645	672	18	of	of	ADP
eurjchem-1645	672	19	10.82	10.82	NUM
eurjchem-1645	672	20	,	,	PUNCT
eurjchem-1645	672	21	8.59	8.59	NUM
eurjchem-1645	672	22	and	and	CCONJ
eurjchem-1645	672	23	8.36	8.36	NUM
eurjchem-1645	672	24	µm	µm	NOUN
eurjchem-1645	672	25	,	,	PUNCT
eurjchem-1645	672	26	respectively	respectively	ADV
eurjchem-1645	672	27	.	.	PUNCT
eurjchem-1645	673	1	it	it	PRON
eurjchem-1645	673	2	is	be	AUX
eurjchem-1645	673	3	inactive	inactive	ADJ
eurjchem-1645	673	4	with	with	ADP
eurjchem-1645	673	5	du‐	du‐	PROPN
eurjchem-1645	673	6	145	145	NUM
eurjchem-1645	673	7	cell	cell	NOUN
eurjchem-1645	673	8	line	line	NOUN
eurjchem-1645	673	9	with	with	ADP
eurjchem-1645	673	10	ic50	ic50	PROPN
eurjchem-1645	673	11	value	value	NOUN
eurjchem-1645	673	12	of	of	ADP
eurjchem-1645	673	13	17.52	17.52	NUM
eurjchem-1645	673	14	µm	µm	NOUN
eurjchem-1645	673	15	with	with	ADP
eurjchem-1645	673	16	pyrimidine	pyrimidine	NOUN
eurjchem-1645	673	17	and	and	CCONJ
eurjchem-1645	673	18	3‐yl‐quinolone	3‐yl‐quinolone	NUM
eurjchem-1645	673	19	groups	group	NOUN
eurjchem-1645	673	20	.	.	PUNCT
eurjchem-1645	674	1	the	the	DET
eurjchem-1645	674	2	compound	compound	PROPN
eurjchem-1645	674	3	15h	15h	PROPN
eurjchem-1645	674	4	having	have	VERB
eurjchem-1645	674	5	pyrimidine	pyrimidine	NOUN
eurjchem-1645	674	6	and	and	CCONJ
eurjchem-1645	674	7	5‐yl‐quinolone	5‐yl‐quinolone	NUM
eurjchem-1645	674	8	groups	group	NOUN
eurjchem-1645	674	9	is	be	AUX
eurjchem-1645	674	10	most	most	ADV
eurjchem-1645	674	11	active	active	ADJ
eurjchem-1645	674	12	in	in	ADP
eurjchem-1645	674	13	mcf‐7	mcf‐7	PROPN
eurjchem-1645	674	14	cell	cell	NOUN
eurjchem-1645	674	15	line	line	NOUN
eurjchem-1645	674	16	with	with	ADP
eurjchem-1645	674	17	ic50	ic50	PROPN
eurjchem-1645	674	18	value	value	NOUN
eurjchem-1645	674	19	of	of	ADP
eurjchem-1645	674	20	6.12	6.12	NUM
eurjchem-1645	674	21	µm	µm	NOUN
eurjchem-1645	674	22	and	and	CCONJ
eurjchem-1645	674	23	a‐549	a‐549	NOUN
eurjchem-1645	674	24	with	with	ADP
eurjchem-1645	674	25	ic50	ic50	PROPN
eurjchem-1645	674	26	value	value	NOUN
eurjchem-1645	674	27	of	of	ADP
eurjchem-1645	674	28	9.13	9.13	NUM
eurjchem-1645	674	29	µm	µm	ADP
eurjchem-1645	674	30	also	also	ADV
eurjchem-1645	674	31	it	it	PRON
eurjchem-1645	674	32	is	be	AUX
eurjchem-1645	674	33	moderately	moderately	ADV
eurjchem-1645	674	34	active	active	ADJ
eurjchem-1645	674	35	in	in	ADP
eurjchem-1645	674	36	hela	hela	PROPN
eurjchem-1645	674	37	and	and	CCONJ
eurjchem-1645	674	38	du‐145	du‐145	NOUN
eurjchem-1645	674	39	cell	cell	NOUN
eurjchem-1645	674	40	lines	line	NOUN
eurjchem-1645	674	41	with	with	ADP
eurjchem-1645	674	42	ic50	ic50	PROPN
eurjchem-1645	674	43	values	value	NOUN
eurjchem-1645	674	44	of	of	ADP
eurjchem-1645	674	45	14.16	14.16	NUM
eurjchem-1645	674	46	and	and	CCONJ
eurjchem-1645	674	47	11.62	11.62	NUM
eurjchem-1645	674	48	µm	µm	NOUN
eurjchem-1645	674	49	,	,	PUNCT
eurjchem-1645	674	50	respectively	respectively	ADV
eurjchem-1645	674	51	.	.	PUNCT
eurjchem-1645	675	1	from	from	ADP
eurjchem-1645	675	2	cell	cell	NOUN
eurjchem-1645	675	3	line	line	NOUN
eurjchem-1645	675	4	data	datum	NOUN
eurjchem-1645	675	5	compounds	compound	VERB
eurjchem-1645	675	6	13c	13c	NOUN
eurjchem-1645	675	7	,	,	PUNCT
eurjchem-1645	675	8	13	13	NUM
eurjchem-1645	675	9	g	g	NOUN
eurjchem-1645	675	10	,	,	PUNCT
eurjchem-1645	675	11	15	15	NUM
eurjchem-1645	675	12	g	g	NOUN
eurjchem-1645	675	13	and	and	CCONJ
eurjchem-1645	675	14	15h	15h	NOUN
eurjchem-1645	675	15	are	be	AUX
eurjchem-1645	675	16	most	most	ADV
eurjchem-1645	675	17	active	active	ADJ
eurjchem-1645	675	18	which	which	PRON
eurjchem-1645	675	19	are	be	AUX
eurjchem-1645	675	20	having	having	AUX
eurjchem-1645	675	21	pyrimidine‐2‐yl	pyrimidine‐2‐yl	VERB
eurjchem-1645	675	22	group	group	NOUN
eurjchem-1645	675	23	and	and	CCONJ
eurjchem-1645	675	24	quinoline3/5‐yl	quinoline3/5‐yl	NOUN
eurjchem-1645	675	25	groups	group	NOUN
eurjchem-1645	675	26	,	,	PUNCT
eurjchem-1645	675	27	compared	compare	VERB
eurjchem-1645	675	28	with	with	ADP
eurjchem-1645	675	29	compounds	compound	NOUN
eurjchem-1645	675	30	having	have	VERB
eurjchem-1645	675	31	3‐methoxy	3‐methoxy	ADJ
eurjchem-1645	675	32	phenyl	phenyl	NOUN
eurjchem-1645	675	33	,	,	PUNCT
eurjchem-1645	675	34	benzofuran	benzofuran	ADJ
eurjchem-1645	675	35	and	and	CCONJ
eurjchem-1645	675	36	benzothiophene	benzothiophene	ADJ
eurjchem-1645	675	37	groups	group	NOUN
eurjchem-1645	675	38	.	.	PUNCT
eurjchem-1645	676	1	the	the	DET
eurjchem-1645	676	2	compound	compound	NOUN
eurjchem-1645	676	3	13c	13c	NOUN
eurjchem-1645	676	4	is	be	AUX
eurjchem-1645	676	5	more	more	ADV
eurjchem-1645	676	6	active	active	ADJ
eurjchem-1645	676	7	than	than	ADP
eurjchem-1645	676	8	compound	compound	NOUN
eurjchem-1645	676	9	13d	13d	NOUN
eurjchem-1645	676	10	as	as	SCONJ
eurjchem-1645	676	11	both	both	PRON
eurjchem-1645	676	12	of	of	ADP
eurjchem-1645	676	13	these	these	DET
eurjchem-1645	676	14	compounds	compound	NOUN
eurjchem-1645	676	15	are	be	AUX
eurjchem-1645	676	16	separated	separate	VERB
eurjchem-1645	676	17	by	by	ADP
eurjchem-1645	676	18	position	position	NOUN
eurjchem-1645	676	19	of	of	ADP
eurjchem-1645	676	20	nitrogen	nitrogen	NOUN
eurjchem-1645	676	21	in	in	ADP
eurjchem-1645	676	22	the	the	DET
eurjchem-1645	676	23	qunioline	qunioline	NOUN
eurjchem-1645	676	24	ring	ring	NOUN
eurjchem-1645	676	25	,	,	PUNCT
eurjchem-1645	676	26	the	the	DET
eurjchem-1645	676	27	3‐methoxy	3‐methoxy	NUM
eurjchem-1645	676	28	compounds	compound	VERB
eurjchem-1645	676	29	with	with	ADP
eurjchem-1645	676	30	benzofuran	benzofuran	NOUN
eurjchem-1645	676	31	and	and	CCONJ
eurjchem-1645	676	32	benzothiophene	benzothiophene	ADJ
eurjchem-1645	676	33	are	be	AUX
eurjchem-1645	676	34	less	less	ADV
eurjchem-1645	676	35	active	active	ADJ
eurjchem-1645	676	36	than	than	ADP
eurjchem-1645	676	37	compounds	compound	NOUN
eurjchem-1645	676	38	having	have	VERB
eurjchem-1645	676	39	pyrimidine‐2‐yl	pyrimidine‐2‐yl	VERB
eurjchem-1645	676	40	substitutions	substitution	NOUN
eurjchem-1645	676	41	.	.	PUNCT
eurjchem-1645	677	1	interestingly	interestingly	ADV
eurjchem-1645	677	2	compounds	compound	VERB
eurjchem-1645	677	3	having	having	AUX
eurjchem-1645	677	4	substituted	substitute	VERB
eurjchem-1645	677	5	4,5,6,7‐tetrahydro	4,5,6,7‐tetrahydro	NUM
eurjchem-1645	677	6	group	group	NOUN
eurjchem-1645	677	7	and	and	CCONJ
eurjchem-1645	677	8	substituted	substitute	VERB
eurjchem-1645	677	9	5,6‐dihydro	5,6‐dihydro	NUM
eurjchem-1645	677	10	groups	group	NOUN
eurjchem-1645	677	11	are	be	AUX
eurjchem-1645	677	12	moderate	moderate	ADJ
eurjchem-1645	677	13	to	to	PART
eurjchem-1645	677	14	active	active	ADJ
eurjchem-1645	677	15	on	on	ADP
eurjchem-1645	677	16	all	all	DET
eurjchem-1645	677	17	four	four	NUM
eurjchem-1645	677	18	cell	cell	NOUN
eurjchem-1645	677	19	lines	line	NOUN
eurjchem-1645	677	20	and	and	CCONJ
eurjchem-1645	677	21	that	that	SCONJ
eurjchem-1645	677	22	substituted	substitute	VERB
eurjchem-1645	677	23	5,6‐dihydro	5,6‐dihydro	NUM
eurjchem-1645	677	24	groups	group	NOUN
eurjchem-1645	677	25	are	be	AUX
eurjchem-1645	677	26	more	more	ADV
eurjchem-1645	677	27	active	active	ADJ
eurjchem-1645	677	28	than	than	ADP
eurjchem-1645	677	29	that	that	PRON
eurjchem-1645	677	30	of	of	ADP
eurjchem-1645	677	31	substituted	substitute	VERB
eurjchem-1645	677	32	4,5,6,7‐tetrahydro	4,5,6,7‐tetrahydro	PROPN
eurjchem-1645	677	33	group	group	NOUN
eurjchem-1645	677	34	.	.	PUNCT
eurjchem-1645	678	1	these	these	PRON
eurjchem-1645	678	2	are	be	AUX
eurjchem-1645	678	3	results	result	NOUN
eurjchem-1645	678	4	from	from	ADP
eurjchem-1645	678	5	both	both	DET
eurjchem-1645	678	6	series	series	NOUN
eurjchem-1645	678	7	of	of	ADP
eurjchem-1645	678	8	compounds	compound	NOUN
eurjchem-1645	678	9	.	.	PUNCT
eurjchem-1645	679	1	there	there	PRON
eurjchem-1645	679	2	is	be	VERB
eurjchem-1645	679	3	not	not	PART
eurjchem-1645	679	4	much	much	ADJ
eurjchem-1645	679	5	difference	difference	NOUN
eurjchem-1645	679	6	in	in	ADP
eurjchem-1645	679	7	their	their	PRON
eurjchem-1645	679	8	inhibitions	inhibition	NOUN
eurjchem-1645	679	9	in	in	ADP
eurjchem-1645	679	10	all	all	DET
eurjchem-1645	679	11	four	four	NUM
eurjchem-1645	679	12	cancer	cancer	NOUN
eurjchem-1645	679	13	cell	cell	NOUN
eurjchem-1645	679	14	lines	line	NOUN
eurjchem-1645	679	15	.	.	PUNCT
eurjchem-1645	680	1	further	far	ADV
eurjchem-1645	680	2	we	we	PRON
eurjchem-1645	680	3	have	have	AUX
eurjchem-1645	680	4	studied	study	VERB
eurjchem-1645	680	5	the	the	DET
eurjchem-1645	680	6	most	most	ADV
eurjchem-1645	680	7	active	active	ADJ
eurjchem-1645	680	8	compounds	compound	NOUN
eurjchem-1645	680	9	13c	13c	NOUN
eurjchem-1645	680	10	,	,	PUNCT
eurjchem-1645	680	11	13	13	NUM
eurjchem-1645	680	12	g	g	NOUN
eurjchem-1645	680	13	,	,	PUNCT
eurjchem-1645	680	14	15	15	NUM
eurjchem-1645	680	15	g	g	NOUN
eurjchem-1645	680	16	and	and	CCONJ
eurjchem-1645	680	17	15h	15h	NUM
eurjchem-1645	680	18	on	on	ADP
eurjchem-1645	680	19	human	human	ADJ
eurjchem-1645	680	20	kinases	kinase	NOUN
eurjchem-1645	680	21	.	.	PUNCT
eurjchem-1645	681	1	the	the	DET
eurjchem-1645	681	2	compounds	compound	NOUN
eurjchem-1645	681	3	13c	13c	NOUN
eurjchem-1645	681	4	,	,	PUNCT
eurjchem-1645	681	5	13	13	NUM
eurjchem-1645	681	6	g	g	NOUN
eurjchem-1645	681	7	,	,	PUNCT
eurjchem-1645	681	8	15	15	NUM
eurjchem-1645	681	9	g	g	NOUN
eurjchem-1645	681	10	and	and	CCONJ
eurjchem-1645	681	11	15h	15h	NOUN
eurjchem-1645	681	12	are	be	AUX
eurjchem-1645	681	13	most	most	ADV
eurjchem-1645	681	14	active	active	ADJ
eurjchem-1645	681	15	in	in	ADP
eurjchem-1645	681	16	cell	cell	NOUN
eurjchem-1645	681	17	line	line	NOUN
eurjchem-1645	681	18	studies	study	NOUN
eurjchem-1645	681	19	,	,	PUNCT
eurjchem-1645	681	20	so	so	ADV
eurjchem-1645	681	21	further	far	ADV
eurjchem-1645	681	22	we	we	PRON
eurjchem-1645	681	23	have	have	AUX
eurjchem-1645	681	24	tested	test	VERB
eurjchem-1645	681	25	for	for	ADP
eurjchem-1645	681	26	its	its	PRON
eurjchem-1645	681	27	activity	activity	NOUN
eurjchem-1645	681	28	against	against	ADP
eurjchem-1645	681	29	a	a	DET
eurjchem-1645	681	30	panel	panel	NOUN
eurjchem-1645	681	31	of	of	ADP
eurjchem-1645	681	32	eight	eight	NUM
eurjchem-1645	681	33	human	human	ADJ
eurjchem-1645	681	34	kinase	kinase	NOUN
eurjchem-1645	681	35	at	at	ADP
eurjchem-1645	681	36	10	10	NUM
eurjchem-1645	681	37	µm	µm	ADP
eurjchem-1645	681	38	concentrations	concentration	NOUN
eurjchem-1645	681	39	.	.	PUNCT
eurjchem-1645	682	1	for	for	ADP
eurjchem-1645	682	2	aurora‐a	aurora‐a	PROPN
eurjchem-1645	682	3	kinase	kinase	PROPN
eurjchem-1645	682	4	compounds	compound	VERB
eurjchem-1645	682	5	,	,	PUNCT
eurjchem-1645	682	6	they	they	PRON
eurjchem-1645	682	7	shows	show	VERB
eurjchem-1645	682	8	73	73	NUM
eurjchem-1645	682	9	,	,	PUNCT
eurjchem-1645	682	10	64	64	NUM
eurjchem-1645	682	11	,	,	PUNCT
eurjchem-1645	682	12	51	51	NUM
eurjchem-1645	682	13	and	and	CCONJ
eurjchem-1645	682	14	57	57	NUM
eurjchem-1645	682	15	%	%	NOUN
eurjchem-1645	682	16	inhibitions	inhibition	NOUN
eurjchem-1645	682	17	,	,	PUNCT
eurjchem-1645	682	18	respectively	respectively	ADV
eurjchem-1645	682	19	.	.	PUNCT
eurjchem-1645	683	1	the	the	DET
eurjchem-1645	683	2	results	result	NOUN
eurjchem-1645	683	3	are	be	AUX
eurjchem-1645	683	4	summarized	summarize	VERB
eurjchem-1645	683	5	in	in	ADP
eurjchem-1645	683	6	table	table	NOUN
eurjchem-1645	683	7	2	2	NUM
eurjchem-1645	683	8	.	.	X
eurjchem-1645	684	1	for	for	ADP
eurjchem-1645	684	2	aurora‐b	aurora‐b	PROPN
eurjchem-1645	684	3	kinase	kinase	PROPN
eurjchem-1645	684	4	,	,	PUNCT
eurjchem-1645	684	5	compound	compound	NOUN
eurjchem-1645	684	6	13c	13c	NOUN
eurjchem-1645	684	7	shows	show	VERB
eurjchem-1645	684	8	41	41	NUM
eurjchem-1645	684	9	%	%	NOUN
eurjchem-1645	684	10	inhi‐	inhi‐	NOUN
eurjchem-1645	684	11	bitions	bition	NOUN
eurjchem-1645	684	12	and	and	CCONJ
eurjchem-1645	684	13	for	for	ADP
eurjchem-1645	684	14	remaining	remaining	ADJ
eurjchem-1645	684	15	compounds	compound	NOUN
eurjchem-1645	684	16	13	13	NUM
eurjchem-1645	684	17	g	g	NOUN
eurjchem-1645	684	18	(	(	PUNCT
eurjchem-1645	684	19	70	70	NUM
eurjchem-1645	684	20	%	%	NOUN
eurjchem-1645	684	21	)	)	PUNCT
eurjchem-1645	684	22	,	,	PUNCT
eurjchem-1645	684	23	15	15	NUM
eurjchem-1645	684	24	g	g	NOUN
eurjchem-1645	684	25	(	(	PUNCT
eurjchem-1645	684	26	77	77	NUM
eurjchem-1645	684	27	%	%	NOUN
eurjchem-1645	684	28	)	)	PUNCT
eurjchem-1645	684	29	and	and	CCONJ
eurjchem-1645	684	30	15h	15h	NUM
eurjchem-1645	684	31	(	(	PUNCT
eurjchem-1645	684	32	73	73	NUM
eurjchem-1645	684	33	%	%	NOUN
eurjchem-1645	684	34	)	)	PUNCT
eurjchem-1645	684	35	inhibitions	inhibition	NOUN
eurjchem-1645	684	36	.	.	PUNCT
eurjchem-1645	685	1	for	for	ADP
eurjchem-1645	685	2	cdk	cdk	PROPN
eurjchem-1645	685	3	/	/	SYM
eurjchem-1645	685	4	cyclina	cyclina	PROPN
eurjchem-1645	685	5	,	,	PUNCT
eurjchem-1645	685	6	cdk	cdk	PROPN
eurjchem-1645	685	7	/	/	SYM
eurjchem-1645	685	8	cycline	cycline	PROPN
eurjchem-1645	685	9	,	,	PUNCT
eurjchem-1645	685	10	egfr	egfr	NOUN
eurjchem-1645	685	11	and	and	CCONJ
eurjchem-1645	685	12	pdk1	pdk1	PROPN
eurjchem-1645	685	13	,	,	PUNCT
eurjchem-1645	685	14	the	the	DET
eurjchem-1645	685	15	inhibition	inhibition	NOUN
eurjchem-1645	685	16	is	be	AUX
eurjchem-1645	685	17	in	in	ADP
eurjchem-1645	685	18	the	the	DET
eurjchem-1645	685	19	range	range	NOUN
eurjchem-1645	685	20	of	of	ADP
eurjchem-1645	685	21	17	17	NUM
eurjchem-1645	685	22	to	to	PART
eurjchem-1645	685	23	37	37	NUM
eurjchem-1645	685	24	%	%	NOUN
eurjchem-1645	685	25	.	.	PUNCT
eurjchem-1645	686	1	cdk5	cdk5	PROPN
eurjchem-1645	686	2	/	/	SYM
eurjchem-1645	686	3	p25	p25	PROPN
eurjchem-1645	686	4	kinase	kinase	NOUN
eurjchem-1645	686	5	and	and	CCONJ
eurjchem-1645	686	6	mtor	mtor	PROPN
eurjchem-1645	686	7	kinase	kinase	PROPN
eurjchem-1645	686	8	the	the	DET
eurjchem-1645	686	9	inhibitions	inhibition	NOUN
eurjchem-1645	686	10	are	be	AUX
eurjchem-1645	686	11	in	in	ADP
eurjchem-1645	686	12	the	the	DET
eurjchem-1645	686	13	range	range	NOUN
eurjchem-1645	686	14	of	of	ADP
eurjchem-1645	686	15	44	44	NUM
eurjchem-1645	686	16	to	to	PART
eurjchem-1645	686	17	70	70	NUM
eurjchem-1645	686	18	%	%	NOUN
eurjchem-1645	686	19	.	.	PUNCT
eurjchem-1645	687	1	for	for	ADP
eurjchem-1645	687	2	aurora‐a	aurora‐a	PROPN
eurjchem-1645	687	3	,	,	PUNCT
eurjchem-1645	687	4	aurora‐b	aurora‐b	NOUN
eurjchem-1645	687	5	,	,	PUNCT
eurjchem-1645	687	6	cdk5	cdk5	PROPN
eurjchem-1645	687	7	/	/	SYM
eurjchem-1645	687	8	p25	p25	PROPN
eurjchem-1645	687	9	and	and	CCONJ
eurjchem-1645	687	10	pawar	pawar	PROPN
eurjchem-1645	687	11	et	et	PROPN
eurjchem-1645	687	12	al	al	PROPN
eurjchem-1645	687	13	.	.	PUNCT
eurjchem-1645	687	14	/	/	SYM
eurjchem-1645	687	15	european	european	PROPN
eurjchem-1645	687	16	journal	journal	PROPN
eurjchem-1645	687	17	of	of	ADP
eurjchem-1645	687	18	chemistry	chemistry	NOUN
eurjchem-1645	687	19	8	8	NUM
eurjchem-1645	687	20	(	(	PUNCT
eurjchem-1645	687	21	4	4	NUM
eurjchem-1645	687	22	)	)	PUNCT
eurjchem-1645	687	23	(	(	PUNCT
eurjchem-1645	687	24	2017	2017	NUM
eurjchem-1645	687	25	)	)	PUNCT
eurjchem-1645	687	26	400‐409	400‐409	PROPN
eurjchem-1645	687	27	409	409	NUM
eurjchem-1645	687	28	mtor	mtor	PROPN
eurjchem-1645	687	29	kinase	kinase	PROPN
eurjchem-1645	687	30	,	,	PUNCT
eurjchem-1645	687	31	all	all	DET
eurjchem-1645	687	32	the	the	DET
eurjchem-1645	687	33	compounds	compound	NOUN
eurjchem-1645	687	34	shows	show	VERB
eurjchem-1645	687	35	promising	promise	VERB
eurjchem-1645	687	36	inhibitions	inhibition	NOUN
eurjchem-1645	687	37	to	to	ADP
eurjchem-1645	687	38	great	great	ADJ
eurjchem-1645	687	39	extent	extent	NOUN
eurjchem-1645	687	40	.	.	PUNCT
eurjchem-1645	688	1	the	the	DET
eurjchem-1645	688	2	inhibition	inhibition	NOUN
eurjchem-1645	688	3	results	result	NOUN
eurjchem-1645	688	4	shows	show	VERB
eurjchem-1645	688	5	compound	compound	NOUN
eurjchem-1645	688	6	13c	13c	NOUN
eurjchem-1645	688	7	is	be	AUX
eurjchem-1645	688	8	active	active	ADJ
eurjchem-1645	688	9	for	for	ADP
eurjchem-1645	688	10	aurora‐a	aurora‐a	PROPN
eurjchem-1645	688	11	kinase	kinase	PROPN
eurjchem-1645	688	12	and	and	CCONJ
eurjchem-1645	688	13	cdk5	cdk5	PROPN
eurjchem-1645	688	14	/	/	SYM
eurjchem-1645	688	15	p25	p25	PROPN
eurjchem-1645	688	16	kinase	kinase	NOUN
eurjchem-1645	688	17	and	and	CCONJ
eurjchem-1645	688	18	it	it	PRON
eurjchem-1645	688	19	shows	show	VERB
eurjchem-1645	688	20	less	less	ADJ
eurjchem-1645	688	21	inhibition	inhibition	NOUN
eurjchem-1645	688	22	for	for	ADP
eurjchem-1645	688	23	remaining	remain	VERB
eurjchem-1645	688	24	kinases	kinase	NOUN
eurjchem-1645	688	25	.	.	PUNCT
eurjchem-1645	689	1	compounds	compound	VERB
eurjchem-1645	689	2	13	13	NUM
eurjchem-1645	689	3	g	g	NOUN
eurjchem-1645	689	4	,	,	PUNCT
eurjchem-1645	689	5	15	15	NUM
eurjchem-1645	689	6	g	g	NOUN
eurjchem-1645	689	7	and	and	CCONJ
eurjchem-1645	689	8	15h	15h	NUM
eurjchem-1645	689	9	shows	show	VERB
eurjchem-1645	689	10	>	>	X
eurjchem-1645	689	11	50	50	NUM
eurjchem-1645	689	12	%	%	NOUN
eurjchem-1645	689	13	inhibitions	inhibition	NOUN
eurjchem-1645	689	14	.	.	PUNCT
eurjchem-1645	690	1	for	for	ADP
eurjchem-1645	690	2	egfr	egfr	NOUN
eurjchem-1645	690	3	,	,	PUNCT
eurjchem-1645	690	4	pdk1	pdk1	PROPN
eurjchem-1645	690	5	,	,	PUNCT
eurjchem-1645	690	6	cdk2/	cdk2/	PROPN
eurjchem-1645	690	7	cycline	cycline	PROPN
eurjchem-1645	690	8	and	and	CCONJ
eurjchem-1645	690	9	cdk2	cdk2	PROPN
eurjchem-1645	690	10	/	/	SYM
eurjchem-1645	690	11	cyclina	cyclina	PROPN
eurjchem-1645	690	12	kinases	kinase	NOUN
eurjchem-1645	690	13	,	,	PUNCT
eurjchem-1645	690	14	most	most	ADJ
eurjchem-1645	690	15	of	of	ADP
eurjchem-1645	690	16	compounds	compound	NOUN
eurjchem-1645	690	17	shows	show	VERB
eurjchem-1645	690	18	<	<	X
eurjchem-1645	690	19	40	40	NUM
eurjchem-1645	690	20	%	%	NOUN
eurjchem-1645	690	21	inhibitions	inhibition	NOUN
eurjchem-1645	690	22	.	.	PUNCT
eurjchem-1645	691	1	4	4	X
eurjchem-1645	691	2	.	.	X
eurjchem-1645	691	3	conclusion	conclusion	NOUN
eurjchem-1645	691	4	we	we	PRON
eurjchem-1645	691	5	have	have	AUX
eurjchem-1645	691	6	synthesized	synthesize	VERB
eurjchem-1645	691	7	3‐(substituted)‐4,5,6,7‐tetrahydro‐6‐	3‐(substituted)‐4,5,6,7‐tetrahydro‐6‐	NUM
eurjchem-1645	691	8	(	(	PUNCT
eurjchem-1645	691	9	substituted)‐1h‐pyrazolo[3	substituted)‐1h‐pyrazolo[3	PROPN
eurjchem-1645	691	10	,	,	PUNCT
eurjchem-1645	691	11	4‐c]pyridine	4‐c]pyridine	NUM
eurjchem-1645	691	12	(	(	PUNCT
eurjchem-1645	691	13	13a‐h	13a‐h	PROPN
eurjchem-1645	691	14	)	)	PUNCT
eurjchem-1645	691	15	and	and	CCONJ
eurjchem-1645	691	16	3‐	3‐	NUM
eurjchem-1645	691	17	(	(	PUNCT
eurjchem-1645	691	18	substituted)‐5	substituted)‐5	NOUN
eurjchem-1645	691	19	,	,	PUNCT
eurjchem-1645	691	20	6‐dihydro‐6‐(substituted)‐1h‐pyrazolo[3	6‐dihydro‐6‐(substituted)‐1h‐pyrazolo[3	NUM
eurjchem-1645	691	21	,	,	PUNCT
eurjchem-1645	691	22	4‐c	4‐c	NOUN
eurjchem-1645	691	23	]	]	X
eurjchem-1645	692	1	pyridin‐7(4h)‐one	pyridin‐7(4h)‐one	X
eurjchem-1645	692	2	(	(	PUNCT
eurjchem-1645	692	3	15a‐h	15a‐h	PROPN
eurjchem-1645	692	4	)	)	PUNCT
eurjchem-1645	692	5	.	.	PUNCT
eurjchem-1645	693	1	the	the	DET
eurjchem-1645	693	2	synthesis	synthesis	NOUN
eurjchem-1645	693	3	mainly	mainly	ADV
eurjchem-1645	693	4	required	require	VERB
eurjchem-1645	693	5	protection	protection	NOUN
eurjchem-1645	693	6	,	,	PUNCT
eurjchem-1645	693	7	deportation	deportation	NOUN
eurjchem-1645	693	8	,	,	PUNCT
eurjchem-1645	693	9	n‐alkylation	n‐alkylation	NOUN
eurjchem-1645	693	10	and	and	CCONJ
eurjchem-1645	693	11	suzuki	suzuki	PROPN
eurjchem-1645	693	12	coupling	coupling	NOUN
eurjchem-1645	693	13	reactions	reaction	NOUN
eurjchem-1645	693	14	.	.	PUNCT
eurjchem-1645	694	1	we	we	PRON
eurjchem-1645	694	2	have	have	AUX
eurjchem-1645	694	3	optimized	optimize	VERB
eurjchem-1645	694	4	all	all	DET
eurjchem-1645	694	5	the	the	DET
eurjchem-1645	694	6	steps	step	NOUN
eurjchem-1645	694	7	for	for	ADP
eurjchem-1645	694	8	clean	clean	ADJ
eurjchem-1645	694	9	reaction	reaction	NOUN
eurjchem-1645	694	10	profile	profile	NOUN
eurjchem-1645	694	11	and	and	CCONJ
eurjchem-1645	694	12	easy	easy	ADJ
eurjchem-1645	694	13	isolation	isolation	NOUN
eurjchem-1645	694	14	of	of	ADP
eurjchem-1645	694	15	all	all	DET
eurjchem-1645	694	16	intermediates	intermediate	NOUN
eurjchem-1645	694	17	and	and	CCONJ
eurjchem-1645	694	18	final	final	ADJ
eurjchem-1645	694	19	com‐	com‐	NOUN
eurjchem-1645	694	20	pounds	pound	NOUN
eurjchem-1645	694	21	.	.	PUNCT
eurjchem-1645	695	1	the	the	DET
eurjchem-1645	695	2	compounds	compound	NOUN
eurjchem-1645	695	3	13a‐h	13a‐h	NOUN
eurjchem-1645	695	4	and	and	CCONJ
eurjchem-1645	695	5	15a‐h	15a‐h	NOUN
eurjchem-1645	695	6	are	be	AUX
eurjchem-1645	695	7	tested	test	VERB
eurjchem-1645	695	8	for	for	ADP
eurjchem-1645	695	9	anti‐	anti‐	PROPN
eurjchem-1645	695	10	proliferative	proliferative	ADJ
eurjchem-1645	695	11	activity	activity	NOUN
eurjchem-1645	695	12	on	on	ADP
eurjchem-1645	695	13	panel	panel	NOUN
eurjchem-1645	695	14	of	of	ADP
eurjchem-1645	695	15	four	four	NUM
eurjchem-1645	695	16	cell	cell	NOUN
eurjchem-1645	695	17	lines	line	NOUN
eurjchem-1645	695	18	.	.	PUNCT
eurjchem-1645	696	1	compounds	compound	NOUN
eurjchem-1645	696	2	with	with	ADP
eurjchem-1645	696	3	pyrimidine‐2‐yl	pyrimidine‐2‐yl	NOUN
eurjchem-1645	696	4	substitutions	substitution	NOUN
eurjchem-1645	696	5	and	and	CCONJ
eurjchem-1645	696	6	quinolone	quinolone	NOUN
eurjchem-1645	696	7	3/5‐yl	3/5‐yl	PROPN
eurjchem-1645	696	8	groups	group	NOUN
eurjchem-1645	696	9	are	be	AUX
eurjchem-1645	696	10	most	most	ADV
eurjchem-1645	696	11	active	active	ADJ
eurjchem-1645	696	12	compared	compare	VERB
eurjchem-1645	696	13	with	with	ADP
eurjchem-1645	696	14	3‐methoxy	3‐methoxy	NUM
eurjchem-1645	696	15	and	and	CCONJ
eurjchem-1645	696	16	benzo‐	benzo‐	PRON
eurjchem-1645	696	17	furane	furane	NOUN
eurjchem-1645	696	18	/	/	SYM
eurjchem-1645	696	19	benzothiophene	benzothiophene	ADJ
eurjchem-1645	696	20	.	.	PUNCT
eurjchem-1645	697	1	compounds	compound	VERB
eurjchem-1645	697	2	13c	13c	NOUN
eurjchem-1645	697	3	,	,	PUNCT
eurjchem-1645	697	4	13	13	NUM
eurjchem-1645	697	5	g	g	NOUN
eurjchem-1645	697	6	,	,	PUNCT
eurjchem-1645	697	7	15	15	NUM
eurjchem-1645	697	8	g	g	NOUN
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eurjchem-1645	697	10	15h	15h	NOUN
eurjchem-1645	697	11	are	be	AUX
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eurjchem-1645	698	8	head	head	NOUN
eurjchem-1645	698	9	,	,	PUNCT
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eurjchem-1645	698	11	of	of	ADP
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eurjchem-1645	698	13	technology	technology	PROPN
eurjchem-1645	698	14	,	,	PUNCT
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eurjchem-1645	698	18	ambedkar	ambedkar	PROPN
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eurjchem-1645	698	25	ms	ms	PROPN
eurjchem-1645	698	26	,	,	PUNCT
eurjchem-1645	698	27	india	india	PROPN
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eurjchem-1645	698	29	providing	provide	VERB
eurjchem-1645	698	30	the	the	DET
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eurjchem-1645	698	32	facility	facility	NOUN
eurjchem-1645	698	33	.	.	PUNCT
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eurjchem-1645	699	4	]	]	PUNCT
eurjchem-1645	699	5	.	.	PUNCT
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eurjchem-1645	700	2	,	,	PUNCT
eurjchem-1645	700	3	a.	a.	NOUN
eurjchem-1645	700	4	m.	m.	NOUN
eurjchem-1645	700	5	;	;	PUNCT
eurjchem-1645	700	6	ashour	ashour	PROPN
eurjchem-1645	700	7	,	,	PUNCT
eurjchem-1645	700	8	a.	a.	PROPN
eurjchem-1645	700	9	e.	e.	PROPN
eurjchem-1645	700	10	;	;	PUNCT
eurjchem-1645	700	11	prasad	prasad	PROPN
eurjchem-1645	700	12	,	,	PUNCT
eurjchem-1645	700	13	o.	o.	PROPN
eurjchem-1645	700	14	;	;	PUNCT
eurjchem-1645	700	15	sinha	sinha	PROPN
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eurjchem-1645	700	17	l.	l.	PROPN
eurjchem-1645	700	18	;	;	PUNCT
eurjchem-1645	700	19	pathak	pathak	PROPN
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eurjchem-1645	700	21	s.	s.	PROPN
eurjchem-1645	700	22	;	;	PUNCT
eurjchem-1645	700	23	alasmari	alasmari	PROPN
eurjchem-1645	700	24	,	,	PUNCT
eurjchem-1645	700	25	f.	f.	PROPN
eurjchem-1645	700	26	a.	a.	PROPN
eurjchem-1645	700	27	;	;	PUNCT
eurjchem-1645	700	28	rishi	rishi	PROPN
eurjchem-1645	700	29	,	,	PUNCT
eurjchem-1645	700	30	a.	a.	PROPN
eurjchem-1645	700	31	k.	k.	PROPN
eurjchem-1645	700	32	;	;	PUNCT
eurjchem-1645	700	33	abdel‐aziz	abdel‐aziz	PROPN
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eurjchem-1645	700	35	h.	h.	PROPN
eurjchem-1645	700	36	a.	a.	PROPN
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eurjchem-1645	703	1	[	[	X
eurjchem-1645	703	2	2	2	NUM
eurjchem-1645	703	3	]	]	PUNCT
eurjchem-1645	703	4	.	.	PUNCT
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eurjchem-1645	704	5	;	;	PUNCT
eurjchem-1645	704	6	seo	seo	PROPN
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eurjchem-1645	704	13	a.	a.	PROPN
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eurjchem-1645	704	15	;	;	PUNCT
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eurjchem-1645	704	17	,	,	PUNCT
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eurjchem-1645	704	19	;	;	PUNCT
eurjchem-1645	704	20	choi	choi	PROPN
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eurjchem-1645	704	22	k.	k.	PROPN
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eurjchem-1645	708	3	]	]	PUNCT
eurjchem-1645	708	4	.	.	PUNCT
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eurjchem-1645	709	5	;	;	PUNCT
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eurjchem-1645	709	10	;	;	PUNCT
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eurjchem-1645	709	13	s.	s.	PROPN
eurjchem-1645	709	14	;	;	PUNCT
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eurjchem-1645	709	19	;	;	PUNCT
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eurjchem-1645	713	4	.	.	PUNCT
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eurjchem-1645	714	2	,	,	PUNCT
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eurjchem-1645	714	4	;	;	PUNCT
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eurjchem-1645	714	6	,	,	PUNCT
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eurjchem-1645	714	8	;	;	PUNCT
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eurjchem-1645	714	12	;	;	PUNCT
eurjchem-1645	714	13	mazzola	mazzola	PROPN
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eurjchem-1645	714	17	;	;	PUNCT
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eurjchem-1645	714	22	;	;	PUNCT
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eurjchem-1645	714	24	,	,	PUNCT
eurjchem-1645	714	25	h.	h.	PROPN
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eurjchem-1645	714	27	;	;	PUNCT
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eurjchem-1645	714	30	k.	k.	PROPN
eurjchem-1645	714	31	;	;	PUNCT
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eurjchem-1645	714	37	lavey	lavey	PROPN
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eurjchem-1645	714	39	b.	b.	PROPN
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eurjchem-1645	714	49	;	;	PUNCT
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eurjchem-1645	714	100	;	;	PUNCT
eurjchem-1645	714	101	yu	yu	PROPN
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eurjchem-1645	714	103	w.	w.	PROPN
eurjchem-1645	714	104	;	;	PUNCT
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eurjchem-1645	715	1	appl	appl	PROPN
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eurjchem-1645	716	4	.	.	PUNCT
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eurjchem-1645	717	8	;	;	PUNCT
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eurjchem-1645	717	13	;	;	PUNCT
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eurjchem-1645	717	64	z.	z.	PROPN
eurjchem-1645	717	65	o.	o.	PROPN
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eurjchem-1645	717	68	,	,	PUNCT
eurjchem-1645	717	69	j.	j.	PROPN
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eurjchem-1645	717	76	.	.	PUNCT
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eurjchem-1645	719	2	.	.	PUNCT
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eurjchem-1645	720	2	,	,	PUNCT
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eurjchem-1645	720	4	,	,	PUNCT
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eurjchem-1645	720	6	.	.	PUNCT
eurjchem-1645	721	1	[	[	X
eurjchem-1645	721	2	6	6	NUM
eurjchem-1645	721	3	]	]	PUNCT
eurjchem-1645	721	4	.	.	PUNCT
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eurjchem-1645	722	2	,	,	PUNCT
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eurjchem-1645	722	8	;	;	PUNCT
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eurjchem-1645	722	12	;	;	PUNCT
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eurjchem-1645	722	25	;	;	PUNCT
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eurjchem-1645	722	38	;	;	PUNCT
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eurjchem-1645	722	40	,	,	PUNCT
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eurjchem-1645	722	42	;	;	PUNCT
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eurjchem-1645	722	47	.	.	PUNCT
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eurjchem-1645	723	2	.	.	PROPN
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eurjchem-1645	723	4	.	.	PUNCT
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eurjchem-1645	724	2	.	.	PROPN
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eurjchem-1645	724	4	,	,	PUNCT
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eurjchem-1645	724	6	,	,	PUNCT
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eurjchem-1645	724	8	.	.	PUNCT
eurjchem-1645	725	1	[	[	X
eurjchem-1645	725	2	7	7	NUM
eurjchem-1645	725	3	]	]	PUNCT
eurjchem-1645	725	4	.	.	PUNCT
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eurjchem-1645	726	2	,	,	PUNCT
eurjchem-1645	726	3	z.	z.	PROPN
eurjchem-1645	726	4	;	;	PUNCT
eurjchem-1645	726	5	yang	yang	PROPN
eurjchem-1645	726	6	,	,	PUNCT
eurjchem-1645	726	7	h.	h.	PROPN
eurjchem-1645	726	8	;	;	PUNCT
eurjchem-1645	726	9	liu	liu	PROPN
eurjchem-1645	726	10	,	,	PUNCT
eurjchem-1645	726	11	z.	z.	PROPN
eurjchem-1645	726	12	;	;	PUNCT
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eurjchem-1645	726	20	;	;	PUNCT
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eurjchem-1645	726	23	s.	s.	PROPN
eurjchem-1645	726	24	;	;	PUNCT
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eurjchem-1645	726	29	;	;	PUNCT
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eurjchem-1645	726	42	;	;	PUNCT
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eurjchem-1645	726	46	;	;	PUNCT
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eurjchem-1645	726	54	;	;	PUNCT
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eurjchem-1645	726	68	.	.	PUNCT
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eurjchem-1645	727	4	.	.	PUNCT
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eurjchem-1645	728	2	.	.	PROPN
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eurjchem-1645	728	4	,	,	PUNCT
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eurjchem-1645	728	6	,	,	PUNCT
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eurjchem-1645	728	8	.	.	PUNCT
eurjchem-1645	729	1	[	[	X
eurjchem-1645	729	2	8	8	NUM
eurjchem-1645	729	3	]	]	PUNCT
eurjchem-1645	729	4	.	.	PUNCT
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eurjchem-1645	730	2	,	,	PUNCT
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eurjchem-1645	730	6	;	;	PUNCT
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eurjchem-1645	730	26	;	;	PUNCT
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eurjchem-1645	730	28	,	,	PUNCT
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eurjchem-1645	730	30	;	;	PUNCT
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eurjchem-1645	730	35	;	;	PUNCT
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eurjchem-1645	730	54	;	;	PUNCT
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eurjchem-1645	730	73	.	.	PUNCT
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eurjchem-1645	731	2	,	,	PUNCT
eurjchem-1645	731	3	50	50	NUM
eurjchem-1645	731	4	,	,	PUNCT
eurjchem-1645	731	5	5339‐5356	5339‐5356	NUM
eurjchem-1645	731	6	.	.	PUNCT
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eurjchem-1645	732	4	.	.	PUNCT
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eurjchem-1645	732	9	;	;	PUNCT
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eurjchem-1645	732	14	;	;	PUNCT
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eurjchem-1645	733	2	,	,	PUNCT
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eurjchem-1645	733	4	,	,	PUNCT
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eurjchem-1645	733	6	.	.	PUNCT
eurjchem-1645	734	1	[	[	X
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eurjchem-1645	734	3	]	]	PUNCT
eurjchem-1645	734	4	.	.	PUNCT
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eurjchem-1645	735	5	;	;	PUNCT
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eurjchem-1645	735	10	;	;	PUNCT
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eurjchem-1645	735	26	.	.	PUNCT
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eurjchem-1645	736	4	.	.	PUNCT
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eurjchem-1645	738	2	,	,	PUNCT
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eurjchem-1645	738	4	,	,	PUNCT
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eurjchem-1645	738	6	.	.	PUNCT
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eurjchem-1645	739	3	]	]	PUNCT
eurjchem-1645	739	4	.	.	PUNCT
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eurjchem-1645	739	9	;	;	PUNCT
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