HCID 66592423, compound → HCID 136170663, compound

Participants

Reaction Steps

10% Pd/C (50 mg) was added to a stirred solution of 5-(2-benzyloxy-phenyl)-isoxazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide (192 mg, 0.33 mmol) (prepared by the method used to generate Intermediate 43) in methanol (50 mL) and stirred under H2 atmosphere with pressure for 3 hrs. The reaction mixture was filtered through celite, the celite was washed with methanol and the filtrate was concentrated under reduced pressure. Washing with ethyl acetate afforded the residue. The residue was purified by preparative HPLC to afford 31 mg (19.1% Yield) of 5-(2-hydroxy-phenyl)-isoxazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 490, 96.83%. 1H NMR (300 MHz, DMSO-d6): δ10.8 (s, 1H), 8.68 (t, 1H), 7.8 (m, 1H), 7.5 (t, 1H), 7.3 (m, 4H), 7.18 (s, 1H), 7.04 (d, 1H), 6.94 (t, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 3.8 (m, 1H), 3.7 (m, 1H), 3.4 (m, 1H), 3.25 (m, 1H), 1.9 (m, 2H), 1.65 (m, 2H).

Provenance & Evidence