[CH2:1]([NH:5][C:6]1[C:7](=[O:14])[N:8]([CH3:13])[N:9]=[CH:10][C:11]=1Cl)[CH2:2][CH2:3][CH3:4].[F:15][C:16]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:17]=1[C:18]([N:20]=[C:21]=[S:22])=[O:19]>O1CCOCC1>[CH2:1]([N:5]1[C:6]2[C:7](=[O:14])[N:8]([CH3:13])[N:9]=[CH:10][C:11]=2[S:22]/[C:21]/1=[N:20]\[C:18](=[O:19])[C:17]1[CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=[CH:26][C:16]=1[F:15])[CH2:2][CH2:3][CH3:4]A mixture of 4-(butylamino)-5-chloro-2-methylpyridazin-3(2H)-one from Example 4A (130 mg, 0.60 mmol) and 2-fluoro-5-(trifluoromethyl)benzoyl isothiocyanate (248 mg, 1 mmol) in dioxane (20 mL) was heated at reflux for 72 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc, washed with saturated aqueous NaHCO3 and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography (hexanes-EtOAc 3:1) to afford 100 mg of the title compound. MS (ESI) m/z 215 (M+H)+.
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