Acetic Acid → HCID 69433732, compound

Participants

Reaction Steps

To a solution of the cis-3-[(4-methyl-1H-indazol-5-yl) oxy]cyclohexanamine (100 mg, 0.407 mmol) obtained in Example 411 in methanol (5 ml) were added 2-chlorobenzaldehyde (46 μl, 0.407 mmol) and acetic acid (23 μl, 0.407 mmol), and the resulting mixture was stirred at room temperature for 30 minutes. Then, acetic acid (46 μl, 0.814 mmol) and sodium cyanoborohydride (28 mg, 0.447 mmol) were added thereto and stirred for 2 hours and a half. Subsequently, the reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=30/1) to obtain cis-N-(2-chlorobenzyl)-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 66%).

Provenance & Evidence