Dichloromethane → n-{(1s,3r)-3-[(Phenylcarbonylamino)methyl]cyclohexyl}[3-(2,4-difluorophenyl)-5-methylisoxazol-4-yl]carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	HCID 22713986	HCID 22713986	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Propan-2-one--dichloromethane (1/1)	HCID 21584124	—
Product	n-{(1s,3r)-3-[(Phenylcarbonylamino)methyl]cyclohexyl}[3-(2,4-difluorophenyl)-5-methylisoxazol-4-yl]carboxamide	HCID 20729729	90%

Reaction Steps

In a fashion similar to that described for preparation 108, a compound from preparation 105 (0.1 g, 0.3 mmol), TFA (2 mL), dichloromethane (1.5 mL), EDCI (0.086 g, 0.45 mmol), DMAP (0.007 g, 0.06 mmol), 3-(2,4-difluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid (0.086 g, 0.36 mmol), and dichloromethane (1.5 mL) gave the title compound (0.123 g, 90%) after column chromatography (silica gel, acetone/dichloromethane gradient). Mass Spectrum (FIA) (m/z) 454.2 [M+1].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06743794B2
Source dataset	uspto-grants-2004_06
ORD ID	ord-233d926a1704468f98d672d892164937
Source note	uspto-grants-2004_06