[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH:17]3[CH2:22][CH2:21][CH:20]([C:23]([NH2:25])=O)[CH2:19][CH2:18]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.O.[OH-].[Na+]>O1CCCC1>[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH:17]3[CH2:18][CH2:19][CH:20]([CH2:23][NH2:25])[CH2:21][CH2:22]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1
Lithium aluminum hydride (58 mg, 1.54 mmol) was added to a solution of the 4-(1H-indazol-5-yloxy)cyclohexanecarboxamide (100 mg, 0.386 mmol) obtained in Example 369 in tetrahydrofuran (3 ml), and the resulting mixture was refluxed. After 6 hours, water (0.087 ml), a 2M-aqueous sodium hydroxide solution (0.176 ml) and then water (0.261 ml) were added to the reaction mixture, and the resulting solution was filtered by the use of Celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol (1%-aqueous ammonia)) to obtain 1-[4-(1H-indazol-5-yloxy)cyclohexyl]methanamine (49 mg, 52%).
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