Acetic Acid → HCID 22933775, compound

Participants

Reaction Steps

Acetic acid (0.12 ml, 2.1 mmol) was added to a suspension of the N-(3-piperidinyl)-1H-indazole-5-carboxamide (0.100 g, 0.409 mmol) obtained in Example 139 and paraformaldehyde (0.101 g, 3.34 mmol) in methanol (3 ml), and the resulting mixture was stirred for 15 minutes and then ice-cooled. Sodium cyanoborohydride (0.128 g, 2.04 mmol) was added thereto and the resulting mixture was slowly warmed up to room temperature and stirred overnight. After a 1N-aqueous sodium hydroxide solution was added thereto, the solvent was distilled off under reduced pressure and the residue was dried up and then purified by a silica gel chromatography (eluent: chloroform/methanol/30% aqueous ammonia=100/10/1). Ethyl acetate was added thereto to precipitate a solid and the resulting suspension was stirred to wash the solid. The solid was collected by filtration and dried under reduced pressure to obtain N-(1-methylpiperidin-3-yl)-1H-indazole-5-carboxamide (0.0718 g, 68%).

Provenance & Evidence