Propanal → HCID 22933631, compound

Participants

Reaction Steps

Acetic acid (0.048 ml) was added to a solution of the N-(4-piperidinyl)-1H-indazole-5-carboxamide (40.0 mg, 0.164 mmol) obtained in Example 58 in methanol (1.2 ml), and the resulting solution was maintained at room temperature for 30 minutes. Propionaldehyde (48.0 mg, 0.826 mmol) was added to the solution and the resulting mixture was maintained at room temperature for another 2 hours. Then, a solution of sodium cyanoborohydride (51.5 mg, 0.820 mmol) in methanol (3.0 ml) was added dropwise thereto, and the resulting mixture was stirred for 18 hours while being maintained at room temperature. A 1N-aqueous sodium hydroxide solution (0.8 ml) was added to the reaction solution, and the resulting mixture was stirred while being maintained at room temperature, and then was concentrated to dryness. The resulting crude product residue was purified by a silica gel column chromatography (eluent: chloroform/methanol/aqueous ammonia=20/1/0.1) to obtain N-(1-propylpiperidin-4-yl)-1H-indazole-5-carboxamide (31 mg, 46%).

Provenance & Evidence