Hydrochloric Acid → 1-(4-Fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)phenyl)methanamine

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Reaction Steps

To a solution of 4-fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrile (3.34 g, 11.8 mmol) in CH2Cl2 (30 mL), ethyl acetate (30.0 mL) and ethanol (30.0 mL) was added 1N HCl (12 mL) followed by 10% palladium on carbon (0.377 g, 3.54 mmol). The mixture was shaken under H2 at 50 psi for 22 h then filtered over CELITE® and concentrated. The solids were triturated with H2O and removed by filtration. The aqueous solution was washed with ethyl acetate and lyophilized to give the title compound, as the HCl salt, as a white powder (3.44 g, 90% yield). LCMS (M+H) calcd for C12H19FN3O2S: 288.11; found: 288.19. 1H NMR (300 MHz, DMSO) δ: 8.35 (2H, brs), 7.71 (1H, dd, J=8.6, 6.4 Hz), 7.54 (1H, dd, J=9.9, 2.6 Hz), 7.43 (1H, td, J=8.4, 2.6 Hz), 4.19 (2H, s), 3.75 (2H, s), 2.63 (3H, s), 1.35 (6H, s).

Provenance & Evidence