F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[F:17][C:18]1([F:26])[CH2:23][CH2:22][CH:21]([CH2:24][NH2:25])[CH2:20][CH2:19]1.CS(C)=O.C(CN)O>O>[F:17][C:18]1([F:26])[CH2:23][CH2:22][CH:21]([CH2:24][NH:25][C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=2[N+:14]([O-:16])=[O:15])[CH2:20][CH2:19]1
N-(4-Fluoro-3-nitrophenyl)ethanesulfonamide (26 g, 0.107 mol), [(4,4-difluorocyclohexyl)methyl]amine (approx. 15 g), DIPFA (20 mL) and DMSO (100 mL) were mixed together and heated to 65° C. overnight. Ethanolamine (5 g) was added and the reaction mixture was stirred until complete disappearance of N-(4-fluoro-3-nitrophenyl)ethanesulfonamide (approx. 4-5 hrs.). The room temperature cooled down reaction mixture was poured in cold water (900 mL). The product was extracted with DCM (5×200 mL). The combined organic phases were washed with HCl 2N (3×200 mL) and dried over anhydrous Na2SO4. The solvent was removed and the crude product was purified on silica gel by flash chromatography (this material can be re-crystallized using a mixture of EtOAc and hexane) to provide the title product (24.2 g) as orange solid.
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