CN(C)C=O.[CH3:6][NH:7][C:8]1[CH:9]=[C:10]([N:16]2[C:25]3[C:20](=[CH:21][C:22]([F:28])=[C:23](F)[C:24]=3[Cl:26])[C:19](=[O:29])[C:18]([C:30]([OH:32])=[O:31])=[CH:17]2)[C:11]([F:15])=[CH:12][C:13]=1[F:14].Cl.Cl.[NH2:35][CH:36]1[CH2:39][NH:38][CH2:37]1.CN1CCCC1>C(O)C>[CH:36]([O:29][CH:19]([CH3:18])[CH3:20])([CH3:39])[CH3:37].[NH2:35][CH:36]1[CH2:39][N:38]([C:23]2[C:24]([Cl:26])=[C:25]3[C:20]([C:19](=[O:29])[C:18]([C:30]([OH:32])=[O:31])=[CH:17][N:16]3[C:10]3[C:11]([F:15])=[CH:12][C:13]([F:14])=[C:8]([NH:7][CH3:6])[CH:9]=3)=[CH:21][C:22]=2[F:28])[CH2:37]1To 650 mg of N,N-dimethylformamide were added 150 mg of 1-(3-methylamino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 110 mg of 3-aminoazetidine dihydrochloride, and 250 mg of N-methylpyrrolidine. The solution was stirred at 90° C. for 1 hour. After 0.5 ml of ethanol was added, the reaction solution was allowed to cool down. The precipitate was collected by filtration and washed with ethanol and then diisopropyl ether to give 130 mg of the title compound.
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