Hydrochloric Acid → Methyl 7-(4-(4-chlorophenethylcarbamoyl)-2-methylphenoxy)-6-cyanochroman-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	2-(4-Chlorophenyl)ethylamine	HCID 67430	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	4-(6-Cyano-4-(methoxycarbonyl)chroman-7-yloxy)-3-methylbenzoic acid	HCID 67080703	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Methyl 7-(4-(4-chlorophenethylcarbamoyl)-2-methylphenoxy)-6-cyanochroman-4-carboxylate	HCID 67080595	34%

Reaction Steps

4-(6-Cyano-4-(methoxycarbonyl)-3,4-dihydro-2H-chromen-7-yloxy)-3-methylbenzoic acid (0.013 g, 0.03539 mmol) in 1 ml dry DMF was treated with N-ethyl-N-isopropylpropan-2-amine (0.01233 ml, 0.07078 mmol), HBTU (0.01610 g, 0.04247 mmol) and 2-(4-chlorophenyl)ethanamine (0.009843 ml, 0.07078 mmol) at ambient temperature. After 48 h, the reaction was poured into 10% aqueous HCl, extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated to provide the crude material as a yellow film. Purification of the crude material on silica gel, eluting with 1% MeOH/DCM, provided the title compound (6 mg, 34%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09096567B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-4f5c403236ef470aaa3cb4effed98a1f
Source note	uspto-grants-2015_08