HCID 66592423, compound → HCID 136170663, compound

HRID 1093758Notes

Reaction equation

HRID 1093758 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)[O: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])[O:9][N:8]=1)=[O:6]

Participants

4

Reactant 1

HCID 66592423HCID 66592423, compound

Product 1

HCID 136170663HCID 136170663, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  1. customprepared by the 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
  6. customafforded the residue
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7d1c3263f3424b7486286118c2bcb720
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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