Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1040306Generated: October 30, 2026

Ethanamine, 2,2,2-trifluoro- → 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-trifluoroethyl)-1-naphthalenecarboxamide

https://huagongshe.com/reaction/1040306

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanamine, 2,2,2-trifluoro-HCID 9773—
ReactantPropylphosphoric anhydrideHCID 16167369—
Reactant4-[5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylic acidHCID 58338630—
ReactantMethyl 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylateHCID 58338637—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventDichloromethaneHCID 6344—
Product4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-trifluoroethyl)-1-naphthalenecarboxamideHCID 16220211—

Reaction Steps

A mixture of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylic acid (i.e. the product from Step C) (190 mg, 0.42 mmol), 4-(dimethylamino)pyridine (77 mg, 0.63 mmol), propylphosphonic anhydride (0.38 mL, 0.63 mmol, 50% in ethyl acetate) and 2,2,2-trifluoroethylamine (0.033 mL, 0.42 mL) in dichloromethane (5 mL) was stirred at room temperature overnight. The reaction mixture was concentrated, and the residue was purified by column chromatography on silica gel using hexanes/ethyl acetate as eluent to give the title product, a compound of the present invention, as a white solid (71 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08552218B2
Source datasetuspto-grants-2013_10
ORD IDord-7f19ce755bab4d4d83659a18cfaaf43f
Source noteuspto-grants-2013_10