HCID 178523508, compound → HCID 178523509, compound

HRID 1093751Notes

Reaction equation

HRID 1093751 reaction equation
[O:1]=[C:2]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)[CH2:28][CH2:27]1)[CH2:3][NH:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18]CC2C=CC=CC=2)[NH:9][N:8]=1)=[O:6]>CO.[Pd]>[O:1]=[C:2]([N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:40])([F:41])[F:42])[CH:34]=2)[CH2:28][CH2:27]1)[CH2:3][NH:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])[NH:9][N:8]=1)=[O:6]

Participants

4

Reactant 1

HCID 178523508HCID 178523508, compound

Product 1

HCID 178523509HCID 178523509, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (50 mg) was added to a stirred solution of 5-(2-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide (195 mg, 0.34 mmol) (prepared by method used for the synthesis of Intermediate 45) in methanol (30 mL) under inert atmosphere 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 58 mg (35% Yield) of 5-(2-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 489, 91.45%. 1H NMR (300 MHz, DMSO-d6): δ8.2 (m, 1H), 7.64 (d, 1H), 7.5 (t, 1H), 7.26 (t, 2H), 7.1 (m, 2H), 6.94 (m, 1H), 6.84 (t, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 3.9 (m, 1H), 3.7 (m, 1H), 3.4 (m, 2H), 1.9 (m, 2H), 1.6 (m, 2H).

Workup

  1. customprepared by method
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe celite was washed with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washWashing with ethyl acetate

Sources & evidence

ORD record
ord-1abbc9f2b0c9481da16935630fc3101a
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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