Acetyl chloride → HCID 66729602, compound

Participants

Reaction Steps

To a solution of N-{3-[4-(2-tert-Butylamino-pyridin-4-yl)-1-piperidin-4-yl-1H-pyrazol-3-yl]-2-fluoro-phenyl}-2,5-difluoro-N-methoxymethyl-benzenesulfonamide (100 mg, 0.159 mmol) (prepared as described in example 8) in DCM (1.5 mL) triethylamine (0.024 mL, 0.175 mmol, 1.1 eq) was added, followed by acetylchloride (0.011 mL, 0.159 mmol, 1 eq) and the solution was stirred at r.t. for 1 h. The reaction mixture was then diluted with DCM and washed with water. The aqueous phase was back extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography (DCM/MeOH/NH3 7N in MeOH 94.5:1) affording 93 mg (87%) of N-{3-[1-(1-Acetyl-piperidin-4-yl)-4-(2-tert-butylamino-pyridin-4-yl)-1H-pyrazol-3-yl]-2-fluoro-phenyl}-2,5-difluoro-N-methoxymethyl-benzenesulfonamide, HPLC (254 nm): Rt: 6.59 min; 1H NMR (DMSO-d6) Shift: 8.18 (s, 1H), 7.77 (d, J=5.2 Hz, 1H), 7.58-7.66 (m, 1H), 7.45-7.58 (m, 3H), 7.23-7.35 (m, 2H), 6.26 (s, 1H), 6.15 (dd, J=1.1, 5.4 Hz, 1H), 5.76 (br. s., 1H), 5.01 (s, 2H), 4.43-4.56 (m, 2H), 3.89-3.97 (m, 1H), 3.30 (s, 3H), 3.17-3.25 (m, 1H), 2.69-2.78 (m, 1H), 2.02-2.16 (m, 2H), 2.05 (s, 3H), 1.94 (qd, J=4.6, 12.1 Hz, 1H), 1.79 (qd, J=4.5, 12.1 Hz, 1H), 1.31 (s, 9H); HRMS (ESI) calcd for C33H38F3N6O4S [M+H]+ 671.2622. found 671.2623.

Provenance & Evidence