Br[CH2:2][C:3]1[CH:25]=[C:24]([Cl:26])[C:6]([C:7]([N:9]2[C:17]3[CH:16]=[CH:15][N:14]=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[C:12]=3[CH:11]=[CH:10]2)=[O:8])=[C:5]([Cl:27])[CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:34][NH2:35]>C(#N)C>[Cl:26][C:24]1[CH:25]=[C:3]([CH2:2][NH:35][CH3:34])[CH:4]=[C:5]([Cl:27])[C:6]=1[C:7]([N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[C:12]=2[CH:11]=[CH:10]1)=[O:8]A solution of N-{1-[4-(bromomethyl)-2,6-dichlorobenzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide (50 mg, 0.107 mmol) in acetonitrile was treated with cesium carbonate (69.74 mg, 0.2140 mmol) and stirred for about 15 minutes. The mixture was cooled to 0° C. followed by the portion wise addition of methyl amine (10.68 mg, 0.16 mmol). The reaction mixture was then stirred at room temperature for about 20 minutes and concentrated under vacuum, followed by addition of ice cold water to give N-(1-{2,6-dichloro-4-[(methylamino)methyl]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide (27.5 mg) as white solid.
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