[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[C:8]=1F)=O.NC(N)=[S:24].N1C=CC=CC=1.CCN(CC)CC>C(O)(C)C>[Cl:13][C:9]1[C:8]2[S:24][C:4]([C:3]3[C:15]([N+:19]([O-:21])=[O:20])=[CH:16][CH:17]=[CH:18][C:2]=3[Cl:1])=[N:6][C:7]=2[CH:12]=[CH:11][N:10]=1A stirred suspension of 2-chloro-N-(2-chloro-3-fluoropyridin-4-yl)-6-nitrobenzamide (3.90 g, 11.2 mmol), thiourea (3.40 g, 44.8 mmol) and pyridine (3.1 mL, 38.1 mmol) in isopropanol (35 mL) under a nitrogen atmosphere, was heated under reflux for 4 hours. After this time, Et3N (9.4 mL, 67.2 mmol) was added and the reaction mixture was heated under reflux for 16 hours. After cooling to room temperature, the volatiles were removed under reduced pressure. The crude residue was triturated with ethyl acetate and the solid was removed by filtration. The resultant filtrate was washed with 10% citric acid, brine, dried over MgSO4 and evaporated under reduced pressure to afford the title compound as a pale orange solid (3.55 g, 97%). 1H NMR (400 MHz, CDCl3): δ 8.51 (d, J=5.5 Hz, 1H), 8.13 (dd, J=1.2, 8.4 Hz, 1H), 7.91 (d, J=5.7 Hz, 1H), 7.87 (dd, J=1.2, 8.3 Hz, 1H), 7.72 (t, J=8.1 Hz, 1H).
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