[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13]([OH:15])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Cl.[CH2:21]([N:23]=[C:24]=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.CNC.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13]([N:23]([CH3:24])[CH3:21])=[O:15])=[CH:7][CH:8]=2)[CH:3]=[N:2]1To a solution of 2-(1H-indazol-5-ylamino)benzoic acid (80 mg, 0.316 mmol) in N,N-dimethylformamide (0.5 ml) were added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (73 mg, 0.379 mmol), hydroxybenzotriazole (58 mg, 0.379 mmol) and a 40%-aqueous dimethylamine solution (107 mg, 0.948 mmol), and the resulting mixture was stirred at room temperature for 4 hours. Then, a 5%-aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with a mixed solvent of ethyl acetate and toluene. The organic layer was washed with a 5%-aqueous sodium hydrogencarbonate solution and then a 5%-aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate/methanol=1/1/0.05) to obtain 2-(1H-indazol-5-ylamino)-N,N-dimethylbenzamide (59 mg, 67%).
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