Ammonia → HCID 22933691, compound

Participants

Reaction Steps

A 28%-aqueous ammonia solution (57.6 mg, 0.948 mmol), 1-hydroxybenzotriazole (58 mg, 0.379 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (73 mg, 0.379 mmol) were added in that order to a solution of 2-(1H-indazol-5-ylamino)benzoic acid (80.0 mg, 0.316 mmol) in N,N-dimethylformamide (0.5 ml), and the resulting mixture was stirred at room temperature for 20 hours. A 5% aqueous sodium hydrogencarbonate solution was added to the reaction solution and stirred, followed by extraction with ethyl acetate/toluene/tetrahydrofuran (2/2/1). The organic phase was washed with a 5% aqueous sodium hydrogencarbonate solution and then a 5%-aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic phase dried was concentrated under reduced pressure and the resulting crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol=50/1 to 20/1) to obtain 2-(1H-indazol-5-ylamino)benzamide (66 mg, 83%).

Provenance & Evidence