[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4](Cl)=[N:5][C:6]1[C:11]([F:12])=[CH:10][N:9]=[CH:8][C:7]=1F.NC(N)=[S:23].N1C=CC=CC=1.CCN(CC)CC>C(O)(C)C>[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4]1[S:23][C:7]2[CH:8]=[N:9][CH:10]=[C:11]([F:12])[C:6]=2[N:5]=1
A suspension of 2,6-dichloro-N-(3,5-difluoropyridin-4-yl)-4-iodobenzimidoyl chloride (8.8 g, 19.7 mmol), thiourea (6.0 g, 78.8 mol) and pyridine (5.4 mL, 66.9 mmol) in isopropanol (80 mL), under a nitrogen atmosphere, was heated under reflux for 6 hours. After this time, the reaction mixture was cooled to 70° C. and Et3N (16.4 mL, 118.1 mmol) was added over 5 minutes and then the resultant mixture was heated under reflux for a further 18 hours. Upon cooling to room temperature, the precipitate obtained was collected by filtration and the filtrate was then partitioned between water and EtOAc. The aqueous phase was further extracted with EtOAc (×2) and the combined organic layers were dried (MgSO4), filtered and concentrated to dryness to afford the title compound as an off-white solid (5.5 g, 66% yield). LCMS (Method D): RT=4.22 min, m/z: 426 [M+H+].
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