p-Toluenesulfonic acid → HCID 66729606, compound

Participants

Reaction Steps

To a solution of crude 2,5-difluoro-N-{2-fluoro-3-[2-(tetrahydro-pyran-2-yl)-2H-pyrazol-3-yl]-phenyl}-N-methoxymethyl-benzene-sulfonamide (1.39 g) in MeOH (20 mL), p-toluenesulfonic acid (100 mg) was added and the solution was stirred at r.t. for 1 h. The reaction mixture was then concentrated under reduced pressure, taken up with AcOEt (100 mL) and washed with sat, aq. NaHCO3 (2×50 mL) and brine (50 mL). the organic phase was dried over Na2SO4 and evaporated to dryness. The crude product was purified by chromatography on silica gel (gradient cyclohexane/AcOEt 6:4 to 1:1) to give 630 mg of 2,5-difluoro-N-[2-fluoro-3-(2H-pyrazol-3-yl)-phenyl]-N-methoxymethyl-benzene-sulfonamide as a white powder (80% yield over two steps). HPLC (254 nm): Rt: 5.86 min; 1H NMR (DMSO-d6) Shift: 13.13 (br. s., 1H), 7.93-8.02 (m, 1H), 7.83 (br. s., 1H), 7.55-7.73 (m, 2H), 7.46-7.53 (m, 1H), 7.18-7.33 (m, 2H), 6.49 (br. s., 1H), 5.10 (s, 2H), 3.36-3.42 (m, 3H); HRMS (ESI) calcd for C17H15F3N3O3S [M+H]+ 3980781. found 398.0779.

Provenance & Evidence