3-(Trifluoromethyl)benzoyl chloride → N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)phenyl]-3-(trifluoromethyl)benzamide

Participants

Reaction Steps

To a solution of N-[6-(3-aminophenoxy)-1,3-benzooxazol-2-yl]cyclopropanecarboxamide (128 mg, 415 μmol) in pyridine (3 mL) were added a solution of 3-(trifluoromethyl)benzoyl chloride prepared above in pyridine (2 mL) and N,N-dimethylpyridine-4-amine (58.9 mg, 482 μmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (10 mL) and ethyl acetate (100 mL). This solution was washed with 0.1N hydrochloric acid (50 mL) and saturated aqueous sodium hydrogencarbonate solution (50 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→80/20) to give the title compound (101 mg, 50%) as a colorless solid.

Provenance & Evidence