[C:1](O)(=O)C.[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C@H:15]3[CH2:20][CH2:19][C@H:18](N)[CH2:17][CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[N:6]1.C=O.[C:24]([BH3-])#[N:25].[Na+].[OH-].[Na+].[ClH:30].C(OCC)C>CO>[ClH:30].[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][C@H:15]3[CH2:20][CH2:19][C@H:18]([N:25]([CH3:24])[CH3:1])[CH2:17][CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[N:6]1Acetic acid (0.05 ml, 0.87 mmol) was added to a solution of the trans-4-(1H-indazol-5-yloxy)cyclohexanamine (0.044 g, 0.19 mmol) obtained in Example 384 and paraformaldehyde (0.040 g, 1.33 mmol) in methanol (4 ml), and the resulting mixture was stirred for 15 minutes and then ice-cooled. Sodium cyanoborohydride (0.055 g, 0.87 mmol) was added thereto and the resulting mixture was slowly warmed up to room temperature and stirred overnight. After a 1N-aqueous sodium hydroxide solution was added thereto, the solvent was distilled off under reduced pressure and the residue was dried up and then purified by a silica gel chromatography (eluent: chloroform/methanol/30%-aqueous ammonia=300/10/3). A solution of the purified residue in ethyl acetate was prepared, followed by adding thereto a 1N-hydrochloric acid-diethyl ether solution (0.5 ml). The solid precipitated was subjected to decantation with ethyl acetate (three times) and then dried up to obtain trans-4-(1H-indazol-5-yloxy)-N,N-dimethylcyclohexanamine monohydrochloride (0.0400 g, 86%).
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