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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1517136Generated: November 2, 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/1517136

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanamine, 2,2,2-trifluoro-HCID 9773—
ReactantPropylphosphoric anhydrideHCID 16167369—
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-(bifluoromethyl)-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 numberUS08231888B2
Source datasetuspto-grants-2012_07
ORD IDord-eac06fa27f304b30b4c64eb18d53172d
Source noteuspto-grants-2012_07