[Cl-].[NH4+].C([N:6](C(C)C)CC)(C)C.[NH:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH:22]3[CH2:27][CH2:26][CH:25]([C:28]([OH:30])=O)[CH2:24][CH2:23]3)=[CH:18][CH:19]=2)[CH:14]=[N:13]1.N.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[NH:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH:22]3[CH2:27][CH2:26][CH:25]([C:28]([NH2:6])=[O:30])[CH2:24][CH2:23]3)=[CH:18][CH:19]=2)[CH:14]=[N:13]1Ammonium chloride (173 ml, 3.23 mmol) and diisopropylethylamine (0.75 ml, 4.30 mmol) were added to a solution of the 4-(1H-indazol-5-yloxy)cyclohexanecarboxylic acid (280 mg, 1.08 mmol) obtained in Example 368 in N,N-dimethylformamide (10 ml). After aqueous ammonia (1 ml) was added thereto to effect dissolution, 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (309 mg, 1.61 mmol) and hydroxybenzotriazole (160 mg, 1.18 mmol) were added thereto. After 16 hours, it was confirmed that the starting material remained. Therefore, 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (309 mg, 1.61 mmol) and hydroxybenzotriazole (160 mg, 1.18 mmol) were further added thereto. After 7 hours, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the resulting mixture was poured into water (100 ml) and extracted with ethyl acetate (50 ml×3) and chloroform (20 ml×2). The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was washed with diethyl ether by repulping to obtain 4-(1H-indazol-5-yloxy)cyclohexanecarboxamide (265 mg, 95%).
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