N.O[N:3]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH:24]1[C:32]2[C:27](=[CH:28][C:29]([NH:33][C:34]3[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=3[C:36](O)=[O:37])=[CH:30][CH:31]=2)[CH:26]=[N:25]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:24]1[C:32]2[C:27](=[CH:28][C:29]([NH:33][C:34]3[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=3[C:36]([NH2:3])=[O:37])=[CH:30][CH:31]=2)[CH:26]=[N:25]1A 28%-aqueous ammonia solution (57.6 mg, 0.948 mmol), 1-hydroxybenzotriazole (58 mg, 0.379 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (73 mg, 0.379 mmol) were added in that order to a solution of 2-(1H-indazol-5-ylamino)benzoic acid (80.0 mg, 0.316 mmol) in N,N-dimethylformamide (0.5 ml), and the resulting mixture was stirred at room temperature for 20 hours. A 5% aqueous sodium hydrogencarbonate solution was added to the reaction solution and stirred, followed by extraction with ethyl acetate/toluene/tetrahydrofuran (2/2/1). The organic phase was washed with a 5% aqueous sodium hydrogencarbonate solution and then a 5%-aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic phase dried was concentrated under reduced pressure and the resulting crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol=50/1 to 20/1) to obtain 2-(1H-indazol-5-ylamino)benzamide (66 mg, 83%).
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