Triethylamine → 2-cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Participants

Reaction Steps

2-Cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (70 mg, 0.24 mmol) was dissolved in dimethyl sulfoxide (2 ml), then at room temperature, triethylamine (50 μl, 0.36 mmol) and (3S)-3-(dimethylamino)pyrrolidine (40 μl, 0.31 mmol) were added. After cooling to room temperature, the reaction liquid was fractionated with ethyl acetate and saturated brine. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, then the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=97:3) to obtain a roughly-purified product (64 mg, 69%).

Provenance & Evidence