[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C@H:11]3[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=O)[CH3:19])[CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[ClH:29].C(OCC)C>O1CCCC1.O>[ClH:29].[CH2:18]([NH:17][C@H:14]1[CH2:13][CH2:12][C@H:11]([O:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:16][CH2:15]1)[CH3:19]The trans-N-[4-(1H-indazol-5-yloxy)cyclohexyl]acetamide (0.066 g, 0.24 mmol) obtained in Example 391 was added to a suspension of lithium aluminum hydride (0.040 g, 1.05 mmol) in tetrahydrofuran (5 ml) and stirred for 12 hours with heating under reflux. The resulting solution was cooled on an ice bath, followed by adding dropwise thereto water (0.05 ml), a 2N-aqueous sodium hydroxide solution (0.10 ml) and water (0.15 ml) in that order. Thereafter, the insoluble material was removed by filtration using Celite. The filtrate was purified by a silica gel chromatography (eluent: chloroform/methanol/30%-aqueous ammonia=10/1/0 to 100/10/1). A solution of the purified material in ethyl acetate was prepared and a 1N-hydrochloric acid/diethyl ether solution (0.5 ml) was added thereto. The solid precipitated was subjected to decantation with ethyl acetate and dried up to obtain trans-N-ethyl-4-(1H-indazol-5-yloxy)cyclohexanamine monohydrochloride (0.057 g, 80%).
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