Acetic Acid → HCID 69431488, compound

Participants

Reaction Steps

Under nitrogen, the cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 0.403 mmol) obtained in Example 411 and 25%-glutaraldehyde (187 mg, 0.448 mmol) were dissolved in methanol (10 ml), and the resulting solution was stirred at room temperature for 40 minutes. Then, sodium cyanoborohydride (51 mg, 0.815 mmol) and acetic acid (0.2 ml) were added thereto, and the resulting mixture was stirred at room temperature for 16 hours. The reaction solution was diluted with chloroform and separated by the addition of a 1N-aqueous sodium hydroxide solution, and the desired compound was further extracted from the aqueous layer with chloroform. The combined chloroform layer was washed with water and then a saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate, and then filtered. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: acetonitrile/aqueous ammonia=100/0, 100/2, 100/4) to obtain 4-methyl-5-[(cis-3-piperidin-1-ylcyclohexyl)oxy]-1H-indazole (91 mg, yield 71.2%) as a white amorphous substance.

Provenance & Evidence