Cl.Cl.[CH3:3][C:4]1[N:5]=[C:6]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[S:7][C:8]=1[C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10].[CH2:23](N(CC)CC)C.Cl[S:31]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=1)(=[O:33])=[O:32].[N+](=C)=[N-]>ClCCl.CCOCC>[CH3:23][O:40][C:38]([C:37]1[CH:41]=[CH:42][C:34]([S:31]([N:14]2[CH2:15][CH2:16][N:11]([C:9]([C:8]3[S:7][C:6]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)=[N:5][C:4]=3[CH3:3])=[O:10])[CH2:12][CH2:13]2)(=[O:33])=[O:32])=[CH:35][CH:36]=1)=[O:39]To a solution of 1-[4-methyl-2-(4-pyridyl)-5-thiazolecarbonyl]piperazine dihydrochloride (180 mg) and triethylamine (253 mg) in dichloromethane (20 ml) was added 4-chlorosulfonylbenzoic acid (108 mg), and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added a solution of diazomethane in ether until the solution remained yellow. The mixture was concentrated and the residue was purified with silica gel column chromatography (ethyl acetate) to give colorless crystals of the title compound (158 mg).
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