5-(2-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide → HCID 178523495, compound
Reaction equation
[Cl:1][C:2]1[CH:39]=[CH:38][CH:37]=[CH:36][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:35])[CH2:12][NH:13][C:14]([C:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27]CC3C=CC=CC=3)[NH:18][N:17]=2)=[O:15])[CH2:7][CH2:6]1>CO.[Pd]>[Cl:1][C:2]1[CH:39]=[CH:38][CH:37]=[CH:36][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:35])[CH2:12][NH:13][C:14]([C:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[OH:27])[NH:18][N:17]=2)=[O:15])[CH2:7][CH2:6]1Participants
4
Procedure
To a solution of 5-(2-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide (0.075 g, 0.00014 mole), in methanol (50 mL) was added 10% Pd/C (0.015 g) and the resulting mixture was stirred under an atmosphere of hydrogen for 1.5 hours. The mixture was then filtered through celite, the celite was washed with methanol and the organic layers were concentrated under reduced pressure. The resulting residue was recrystallized from a mixture of ethyl acetate and methanol to afford 0.052 g (83%) of 5-(2-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 455.16 (M+1)+, 90.34%, 1H NMR (DMSO-d6): δ 13.2 (s, 1H), 10.2 (s, 1H), 8.0 (s, 1H), 7.64 (m, 1H), 7.42 (m, 1H), 7.24 (m, 2H), 7.18 (m, 1H), 7.06 (s, 1H), 6.96 (m, 2H), 6.84 (t, 1H), 4.7 (m, 1H), 4.2 (d, 2H), 3.61 (m, 2H), 3.4 (m, 2H), 1.9 (m, 2H), 1.6 (m, 2H).