Ammonia → 1-Amino-3-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)cyclopentanecarbonitrile

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Reaction Steps

A mixture of 3-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)cyclopentanone (Preparation 121C, 230 mg, 0.495 mmol), ammonium chloride (79 mg, 1.486 mmol), sodium cyanide (72.8 mg, 1.486 mmol), 7 M methanol solution of ammonia (4.95 mL, 34.7 mmol) and dichloromethane (2 mL) was stirred at room temperature for 1 day. Additional 7 M methanol solution of ammonia (2 mL) was added and the mixture was stirred at room temperature for 2.5 days. The mixture was concentrated. The residue was partitioned between ethyl acetate (10 mL) and saturated aqueous sodium bicarbonate solution (3 mL). The aqueous layer was separated and extracted with ethyl acetate (2×1.5 mL). The combined ethyl acetate extracts were dried (sodium sulfate) and concentrated under reduced pressure to give 1-amino-3-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)cyclopentanecarbonitrile (245 mg, 0.500 mmol, 100% yield) as a glassy solid. The compound had an HPLC retention time=3.51 min. (condition C); LC/MS M+1=491.2.

Provenance & Evidence