Triethylamine → HCID 68584029, compound

Participants

Reaction Conditions

Reaction Steps

6-Acetyl-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-82) (130 mg, 0.50 mmol) was dissolved in dimethyl sulfoxide (2.6 ml), triethylamine (177 μl, 1.26 mmol) and (3S)-3-(dimethylamino)pyrrolidine (96 μl, 0.76 mmol) were added, followed by stirring at 90° C. for 6 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to preparative thin-layer silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (10:1, v/v) followed by recrystallization and purification with a mixed solvent of diethyl ether/ethyl acetate/n-hexane to obtain the entitled compound (103 mg, 57%) as a red white solid.

Provenance & Evidence