HCID 178474107, compound → HCID 178474106, compound

Participants

Reaction Steps

A solution of 3-[4-acetamido-2-benzyloxyphenyl]-4-[4-(benzyloxycarbonyl)piperazin-1-yl]-1H-pyrazole (70 mg, 133.2 μmol) in MeOH (7 mL) was degassed (3× vacuum/nitrogen) and palladium (10% on carbon; 10 mg, cat.) added. The reaction mixture was again degassed (3× vacuum/nitrogen) and the atmosphere replaced with one of hydrogen (3× vacuum/hydrogen). The mixture was shaken at room temperature for 18 hours. The catalyst was removed by filtration through a small pad of celite and washed with further MeOH (15 mL). The solvent was removed in vacuo to give crude product, which was purified by preparative HPLC to give 3-[4-acetamido-2-hydroxyphenyl]-4-(piperazin-1-yl)-1H-pyrazole (16.3 mg, 41%) as a white solid; δH (MeOH-d4) 8.47 (1H, s), 7.80 (1H, br s), 7.68 (1H, s), 7.26 (1H, s), 7.11 (1H, dd, J=8.5, 2.1 Hz), 3.34-3.29 (4H, m), 3.11-3.07 (4H, m), 2.12 (3H, s); LCMS retention time 1.26 min, M+H+ 302.3.

Provenance & Evidence