[N-:1]=[C:2]=[S:3].[NH4+].[Cl:5][C:6]1[CH:11]=[C:10]([C:12](Cl)=[O:13])[CH:9]=[C:8]([Cl:15])[N:7]=1.Cl.[F:17][C:18]1[C:23]([F:24])=[C:22]([F:25])[CH:21]=[CH:20][C:19]=1[NH2:26]>CC(C)=O>[Cl:5][C:6]1[CH:11]=[C:10]([C:12]([NH:1][C:2]([NH:26][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[C:23]([F:24])[C:18]=2[F:17])=[S:3])=[O:13])[CH:9]=[C:8]([Cl:15])[N:7]=1Ammonium isothiocyanate (7.726 g, 0.1015 mol) was added to a solution of 2,6-dichloro-4-pyridinecarbonyl chloride (17.8 g, 0.0846 mol) in acetone (300 ml). The mixture was stirred for 30 minutes and subsequently 2,3,4-trifluorobenzenamine hydrochloric acid (.HCl) was added slowly. The reaction mixture was stirred at room temperature for 2 hours and was then quenched with H2O (100 ml). The mixture was extracted with CH2Cl2 (3×80 ml) and the combined organic layers were dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (eluent: heptane/EtOAc from 80/20 to 50/50). The desired fractions were collected and the solvent was evaporated in vacuo. Yield: 22.2 g of intermediate D9 (69%).
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