Ethanol → 2-(3-chloro-4-methanesulfonyl-phenyl)-N-[1-(2-hydroxy-ethyl)-1H-pyrazol-3-yl]-3-(tetrahydro-pyran-4-yl)-propionamide

Participants

Reaction Conditions

Reaction Steps

In a flask containing N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-yl}-2-(3-chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionamide (150 mg, 0.26 mmol) was added ethanol (5 mL) and concentrated hydrochloric acid (three drops) and was stirred at 25° C. for 30 minutes. It was then diluted with ethyl acetate (50 mL) and washed with water (1×20 mL) and saturated aqueous brine solution (1×20 mL). The organic layer was then dried over sodium sulfate and absorbed onto silica gel (2 g) and purified on Biotage Flash purification system (40S column, silica gel, 5% methanol/ethyl acetate) which afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-N-[1-(2-hydroxy-ethyl)-1H-pyrazol-3-yl]-3-(tetrahydro-pyran-4-yl)-propionamide (107 mg, 89%) as a white foam: ES-HRMS m/e calcd for C20H26N3O5SCl (M+H)+ 456.1355, observed 456.1354; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.27 (m, 2H, CH2), 1.29-1.42 (m, 1H, CH of CH2), 1.49-1.70 (m, 3H, CH of CH2 and CH2), 2.00-2.14 (m, 1H, CH), 3.20 (m, 2H, OCH2), 3.34 (s, 3H, SO2CH3), 3.67 (q, J=5.5 Hz, 2H, OCH2), 3.75-3.86 (m, 2H, OCH2), 3.95-4.08 (m, 3H, CH and NCH2), 4.83 (t, J=5.3 Hz, 1H, OH), 6.41 (d, J=2.3 Hz, 1H, Ar), 7.54 (d, J=2.3 Hz, 1H, Ar), 7.60 (dd, Jo=8.2 Hz, Jm=1.6 Hz, 1H, Ar), 7.71 (d, Jm=1.6 Hz, 1H, Ar), 8.01 (d, Jo=8.2 Hz, 1H, Ar), 10.81 (s, 1H, NH).

Provenance & Evidence