Sodium cyanoborohydride (484 mg, 7.70 mmol) and then acetic acid (440 μl, 7.68 mmol) were added to a solution of the 1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (335 mg, 1.54 mmol) obtained in Example 317, (e) and 8-propyl-8-azabicyclo[3.2.1]octan-3-one (300 mg, 1.85 mmol) in methanol (6 ml), and the resulting mixture was stirred at room temperature for 1 day. Aqueous ammonia was added thereto, followed by extraction with ethyl acetate. 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. The residue was purified by a silica gel column chromatography (chloroform/methanol/triethylamine=100/1/5) to obtain N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (413 mg, 73%).
