Acetic Acid → HCID 69433407, compound

Participants

Reaction Steps

Isonicotinaldehyde (42.8 μl, 0.45 mmol) and acetic acid (0.23 mL, 4.08 mmol) were added to a methanolic solution (5 ml) of the cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 0.41 mmol) obtained in Example 411, and the resulting mixture was stirred for 10 minutes. Then, sodium cyanoborohydride (28.2 mg, 0.45 mmol) was added thereto and stirred for 2 hours. An aqueous sodium hydroxide solution was added to the reaction solution, followed by extraction with chloroform (three times), and the extract solution was dried over anhydrous magnesium sulfate. The residue was purified by a silica gel chromatography (ethyl acetate, methanol (5% aqueous ammonia): chloroform=10/100) to obtain N-{cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}-N-(pyridin-4-ylmethyl)amine (58.7 mg, 43%).

Provenance & Evidence