[CH3:1][N:2]1[C:6]([C:7](Cl)=[O:8])=[CH:5][N:4]=[CH:3]1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([NH:19]O)=[NH:18])=[N:15][CH:16]=1.O>N1C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:19]=[C:7]([C:6]3[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=3)[O:8][N:18]=2)=[N:15][CH:16]=1A mixture of 3-methyl-3H-imidazole-4-carbonyl chloride (91 mg, 0.5 mmol), 5-chloro-N-hydroxy-pyridine-2-carboxamidine (85.8 mg, 0.5 mmol) in pyridine (5 ml) was refluxed for 4 h and then cooled to room temperature. To the solution was added water (20 ml) and the product precipitated from the solution. The solid was collected by filtration and washed with water, dried to give 6 mg (5%) of the title compound. 1H NMR (CDCl3): 8.78 (d, J=2.4 Hz, 1H), 8.15 (d, J=8.4 Hz, 1H), 8.05 (s, 1H), 7.87 (dd, J=2.7 Hz, J=8.7 Hz, 1H), 7.70 (s, 1H), 4.14 (s, 3H).
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