HCID 66953970, compound → HCID 59559570, compound

HRID 1178126Notes

Reaction equation

HRID 1178126 reaction equation
[O:1]=[C:2]([N:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:43])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]([F:42])([F:41])[F:40])[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]=[C:14]([O:18]CC3C=CC=CC=3)[CH:13]=2)[O:9][N:8]=1)=[O:6]>CO.[Pd]>[O:1]=[C:2]([N:26]1[CH2:27][CH2:28][N:29]([C:32](=[O:43])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]([F:40])([F:42])[F:41])[CH2:30][CH2:31]1)[CH2:3][NH:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[O:9][N:8]=1)=[O:6]

Participants

4

Reactant 1

HCID 66953970HCID 66953970, compound

Product 1

HCID 59559570HCID 59559570, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/c (40 mg) was added to a stirred solution of 5-(3-benzyloxy-phenyl)-isoxazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide (74 mg, 0.12 mmol) (prepared by the method as described above) in MeOH (30 mL) and stirred under hydrogen atmosphere. The reaction mixture was then stirred for 6 hrs. The mixture was filtered over a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to afford 26 mg (41.9% yield) of 5-(3-hydroxy-phenyl)-isoxazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 99.07%. 1H NMR (CD3OD): δ 7.64 (m, 4H), 7.5 (d, 1H), 7.32 (m, 1H), 7.24 (s, 1H), 6.98 (m, 2H), 4.26 (m, 2H), 3.7 (m, 4H), 3.5 (m, 2H), 3.38 (m, 1H), 3.24 (m, 1H).

Workup

  1. customprepared by the method
  2. stirringThe reaction mixture was then stirred for 6 hrs
  3. filtrationThe mixture was filtered over a bed of celite
  4. washThe celite was washed with MeOH
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c7dffda5098420b895b1e20cc950b05
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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