Trifluoroacetic acid → HCID 86721867, compound

Participants

Reaction Steps

To a solution of 4-{4-[(4-fluoro-benzyl)-isobutyl-sulfamoyl]-phenylamino}-piperidine-1-carboxylic acid tert-butyl ester (208 mg) in DCM (9 mL) was added TFA (1 mL) and the reaction was stirred at room temperature for 30 minutes. The reaction was concentrated and purified by SCX column eluting with 2 M NH3 in MeOH to give N-(4-fluoro-benzyl)-N-isobutyl-4-(piperidin-4-ylamino)-benzenesulfonamide. A solution of the crude product (149 mg) in DCM (5 mL) was added DIPEA (124 μL, 711 μmol) followed by methane sulfonylchloride (28 μL, 356 μmol) and the reaction stirred at room temperature for 30 minutes. Water was then added, passed through a phase separator, extracted once more through a phase separator, concentrated and purified by silica gel column chromatography (0-75% EtOAc in cyclohexane) to give the title compound (139 mg). 1H NMR (400 MHz, DMSO): δ 7.51 (d, J=8.7 Hz, 2H), 7.4 (dd, J=8.5, 5.6 Hz, 2H), 7.15 (t, J=8.8 Hz, 2H), 6.71 (d, J=8.7 Hz, 2H), 6.55 (d, J=7.8 Hz, 1H), 4.15 (s, 2H), 3.48-3.53 (m, 3H), 2.93 (d, J=11.6 Hz, 2H), 2.89 (s, 3H), 2.76 (d, J=7.4 Hz, 2H), 1.99 (m, 2H), 1.44-1.49 (m, 3H), 0.65 (d, J=6.6 Hz, 6H). LCMS (m/z, Method B) ES+ 498.0 [M+1]+.

Provenance & Evidence