Trifluoroacetic acid water → HCID 56653051, compound

Participants

Reaction Steps

N-{3-[4-(2-tert-Butylamino-pyridin-4-yl)-1-ethyl-1H-pyrazol-3-yl]-2-fluoro-phenyl}-2,5-difluoro-N-methoxymethyl-benzenesulfonamide (250 mg, 0.436 mmol) was treated with TFA/H2O 9:1 (3 mL) at 70° C. for 4.5 h. The reaction mixture was then evaporated to dryness, taken up with AcOEt and washed with sat, aq. NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (DCM/MeOH/NH3 7M in MeOH 90:8:2) and then treated with ethyl ether, filtered and dried to give 78 mg of N-{3-[4-(2-Amino-pyridin-4-yl)-1-ethyl-1H-pyrazol-3-yl]-2-fluoro-phenyl}-2,5-difluoro-benzene-sulfonamide as a white solid. HPLC (254 nm): Rt: 5.13 min; 1H NMR (DMSO-d6) Shift: 10.75 (br. s., 1H), 8.13 (s, 1H), 7.67 (dd, J=0.5, 5.4 Hz, 1H), 7.50-7.59 (m, 1H), 7.41-7.50 (m, 2H), 7.30 (td, J=24, 7.4 Hz, 1H), 7.12-7.26 (m, 2H), 6.27 (d, J=0.7 Hz, 1H), 6.08 (dd, J=14, 5.4 Hz, 1H), 5.82 (br. s., 2H), 4.18 (q, J=7.2 Hz, 2H), 1.42 (t, J=7.3 Hz, 3H); HRMS (ESI) calcd for C22H19F3N5O2S [M+H]+ 474.1206. found 474.1184.

Provenance & Evidence