Acetic Acid → HCID 178431640, compound

Participants

Reaction Steps

A 36% aqueous formalin solution (161 μl, 1.93 mmol) was added to a methanolic solution (2 ml) of the cis-4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 0.386 mmol) obtained in Example 658, and the resulting mixture was stirred at room temperature for 1 hour. Sodium cyanoborohydride (51 mg, 0.771 mmol) and acetic acid (110 μl, 1.92 mmol) were added thereto, and the resulting mixture was stirred at room temperature for 18 hours. The methanol was removed by the use of nitrogen gas and chloroform-1N-aqueous sodium hydroxide solution was added to the residue, followed by extraction with chloroform. The extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby a crude product was obtained. The crude product was purified by a preparative thin-layer silica gel chromatography (chloroform/methanol/aqueous ammonia=7:1:0.1) to obtain cis-N-{4-[(4,7-dimethyl-1H-indazol-5-yl)oxy]cyclohexyl}-N,N-dimethylamine (77 mg, 69%).

Provenance & Evidence