[CH3:1][C:2]1([CH3:18])[NH:6][S:5](=[O:8])(=[O:7])[N:4]([C:9]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH2:3]1.[H-].[Na+].I[CH3:22]>CN(C=O)C.O>[F:17][C:15]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([N:4]2[CH2:3][C:2]([CH3:18])([CH3:1])[N:6]([CH3:22])[S:5]2(=[O:8])=[O:7])[CH:16]=1To a solution of 2-(4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-fluorobenzonitrile (3.18 g, 11.81 mmol) in DMF (40 mL) was added NaH (0.312 g, 12.99 mmol) and the mixture stirred for 5 min. Iodomethane (1.477 mL, 23.62 mmol) was added and the mixture stirred at 90° C. for 2 h then at room temperature for 16 h. The mixture was diluted with H2O and extracted with ethyl acetate. The organic phase was washed two times with H2O followed by brine, dried (Na2SO4), filtered and concentrated to give the title compound as a white solid (3.35 g, 100% yield). LCMS (M+H) calcd for C12H15FN3O2S: 284.08; found: 284.14. 1H NMR (300 MHz, CDCl3) δ: 7.70-7.61 (2H, m), 7.11-7.05 (1H, m), 3.80 (2H, s), 2.73 (3H, s), 1.42 (6H, s).
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