[C:1]([OH:4])(=O)[CH3:2].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH:34]1[C:42]2[C:37](=[CH:38][C:39]([O:43][C@H:44]3[CH2:49][CH2:48][C@H:47]([NH2:50])[CH2:46][CH2:45]3)=[CH:40][CH:41]=2)[CH:36]=[N:35]1.[OH-].[Li+]>CN(C)C=O.O>[NH:34]1[C:42]2[C:37](=[CH:38][C:39]([O:43][C@H:44]3[CH2:49][CH2:48][C@H:47]([NH:50][C:1](=[O:4])[CH3:2])[CH2:46][CH2:45]3)=[CH:40][CH:41]=2)[CH:36]=[N:35]1
Acetic acid (0.033 g, 0.58 mmol), triethylamine (0.12 ml, 0.86 mmol), 1-hydroxybenztriazole (0.088 g, 0.65 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (0.124 g, 0.65 mmol) were added to a solution of the trans-4-(1H-indazol-5-yloxy)cyclohexanamine (0.100 g, 0.44 mmol) obtained in Example 384 in N,N-dimethylformamide (5 ml) and stirred overnight. A 2N-aqueous lithium hydroxide solution (2 ml) was added thereto and stirred for some time, and the resulting mixture was added to water and extracted three times with toluene/ethyl acetate=1/1. The organic layer was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the solid precipitated was suspended in a hexane/ethyl acetate mixed solvent and stirred to be washed. The solid was collected by filtration and dried under reduced pressure to obtain trans-N-[4-(1H-indazol-5-yloxy)cyclohexyl]acetamide (0.097 g, 82%).
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