PMC:7291971 / 48713-49318 JSON TXT

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Id	Subject	Object	Predicate	Lexical cue
T988	46-55	CHEBI:36357;CHEBI:36357	denotes	compounds
T989	75-83	CHEBI:75958;CHEBI:75958	denotes	solution
T990	150-157	CHEBI:15858;CHEBI:15858	denotes	bromide
T991	158-165	CHEBI:33893;CHEBI:33893	denotes	reagent
T992	260-267	CHEBI:60004;CHEBI:60004	denotes	mixture
T993	306-313	CHEBI:15377;CHEBI:15377	denotes	aqueous
T994	414-420	CHEBI:34683;CHEBI:34683	denotes	Na2SO4
T995	509-515	CHEBI:30563;CHEBI:30563	denotes	silica
T996	542-546	CHEBI:32145;CHEBI:32145	denotes	MeOH
T997	575-583	CHEBI:36357;CHEBI:36357	denotes	compound
T38632	46-55	CHEBI:36357;CHEBI:36357	denotes	compounds
T27381	75-83	CHEBI:75958;CHEBI:75958	denotes	solution
T70032	150-157	CHEBI:15858;CHEBI:15858	denotes	bromide
T50931	158-165	CHEBI:33893;CHEBI:33893	denotes	reagent
T24500	260-267	CHEBI:60004;CHEBI:60004	denotes	mixture
T75121	306-313	CHEBI:15377;CHEBI:15377	denotes	aqueous
T6076	414-420	CHEBI:34683;CHEBI:34683	denotes	Na2SO4
T31885	509-515	CHEBI:30563;CHEBI:30563	denotes	silica
T20744	542-546	CHEBI:32145;CHEBI:32145	denotes	MeOH
T50504	575-583	CHEBI:36357;CHEBI:36357	denotes	compound

Id	Subject	Object	Predicate	Lexical cue	tao:has_database_id
847	103-106	Chemical	denotes	NMP	MESH:C038678
848	414-420	Chemical	denotes	Na2SO4
849	509-519	Chemical	denotes	silica gel	MESH:D058428
850	542-546	Chemical	denotes	MeOH
851	550-553	Chemical	denotes	DCM

Id	Subject	Object	Predicate	Lexical cue
T325	73-74	http://purl.obolibrary.org/obo/CLO_0001020	denotes	a
T326	362-369	http://purl.obolibrary.org/obo/OBI_0100026	denotes	organic
T327	362-369	http://purl.obolibrary.org/obo/UBERON_0000468	denotes	organic
T328	587-588	http://purl.obolibrary.org/obo/CLO_0001020	denotes	a

Id	Subject	Object	Predicate	Lexical cue	chebi_id
T915	75-83	Chemical	denotes	solution	http://purl.obolibrary.org/obo/CHEBI_75958
T916	103-106	Chemical	denotes	NMP	http://purl.obolibrary.org/obo/CHEBI_17188\|http://purl.obolibrary.org/obo/CHEBI_25608\|http://purl.obolibrary.org/obo/CHEBI_7307
T919	150-157	Chemical	denotes	bromide	http://purl.obolibrary.org/obo/CHEBI_15858
T920	158-165	Chemical	denotes	reagent	http://purl.obolibrary.org/obo/CHEBI_33893
T921	260-267	Chemical	denotes	mixture	http://purl.obolibrary.org/obo/CHEBI_60004
T922	285-290	Chemical	denotes	AcOEt	http://purl.obolibrary.org/obo/CHEBI_27750
T923	339-344	Chemical	denotes	AcOEt	http://purl.obolibrary.org/obo/CHEBI_27750
T924	414-420	Chemical	denotes	Na2SO4	http://purl.obolibrary.org/obo/CHEBI_32149
T925	509-515	Chemical	denotes	silica	http://purl.obolibrary.org/obo/CHEBI_30563
T926	542-546	Chemical	denotes	MeOH	http://purl.obolibrary.org/obo/CHEBI_17790
T927	550-553	Chemical	denotes	DCM	http://purl.obolibrary.org/obo/CHEBI_15767

Id	Subject	Object	Predicate	Lexical cue	hp_id
T18	550-553	Phenotype	denotes	DCM	http://purl.obolibrary.org/obo/HP_0001644

Id	Subject	Object	Predicate	Lexical cue
T50	33-42	http://purl.obolibrary.org/obo/GO_0009058	denotes	synthesis

Id	Subject	Object	Predicate	Lexical cue
T352	0-69	Sentence	denotes	4.1.13 General method D for the synthesis of compounds 23, 24 and 25
T353	70-113	Sentence	denotes	To a solution of 20 in anhydrous NMP (conc.
T354	114-195	Sentence	denotes	0.03 M) was added the corresponding bromide reagent (3.00 eq) and DIEA (3.00 eq).
T355	196-301	Sentence	denotes	After stirring for 4 h at 110 °C under microwaves, the reaction mixture was diluted with AcOEt and brine.
T356	302-451	Sentence	denotes	The aqueous layer was extracted with AcOEt and the combined organic extracts were washed with brine, dried over Na2SO4 and concentrated under vacuum.
T357	452-605	Sentence	denotes	The residue was purified by flash column chromatography (silica gel, linear gradient 0–4% MeOH in DCM) to give the desired compound as a colorless solid.