Acetic Acid → HCID 69434568, compound

Participants

Reaction Steps

Under nitrogen, the cis-3-[(4-methoxy-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 0.383 mmol) obtained in Example 583 and 36%-formaldehyde (160 mg, 1.91 mmol) were suspended in a mixture of acetonitrile (2 ml) and methanol (2 ml), and the resulting suspension was stirred at room temperature for 20 minutes. Then, sodium cyanoborohydride (48 mg, 0.765 mmol) and acetic acid (0.2 ml) were added thereto, and the resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with chloroform, washed successively with a 1N-aqueous sodium hydroxide solution, water and 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: chloroform/methanol=20/1, chloroform/methanol/aqueous ammonia=20/1/0.1). The residue purified was dissolved in isopropyl alcohol and a 4N-hydrochloric acid/dioxane solution was added thereto and stirred. Then, the solvent was distilled off under reduced pressure to obtain N-[cis-3-[(4-methoxy-1H-indazol-5-yl)oxy]cyclohexyl]-N,N-dimethylamine monohydrochloride (43 mg, yield 34%).

Provenance & Evidence