4-Cyano-7-(4-methoxybenzylamino)-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide → 7-amino-4-cyano-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

Participants

Reaction Steps

4-Cyano-7-(4-methoxybenzylamino)-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-337) (2.10 g, 4.77 mmol) was dissolved in trifluoroacetic acid (22 ml), and stirred at room temperature for 13 hours. The solvent was evaporated away under reduced pressure, and the resulting residue was added to chloroform (25 ml) and an aqueous saturated sodium hydrogencarbonate solution (25 ml), followed by vigorously stirring for 15 minutes. The organic layer was separated, the aqueous layer was further extracted twice with chloroform. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:acetone=98:2, v/v) to obtain the entitled compound (1.456 g, 95%) as a brown solid.

Provenance & Evidence