HCID 178523553, compound → HCID 178523554, compound

HRID 1178134Notes

Reaction equation

HRID 1178134 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:41]([F:44])([F:43])[F:42])=[C:6]([CH:40]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:39])[CH2:16][NH:17][C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31]CC3C=CC=CC=3)[NH:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1)=[O:8]>CO.C1COCC1.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:41]([F:44])([F:42])[F:43])=[C:6]([CH:40]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:39])[CH2:16][NH:17][C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[OH:31])[NH:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1)=[O:8]

Participants

5

Reactant 1

HCID 178523553HCID 178523553, compound

Product 1

HCID 178523554HCID 178523554, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Pd/c (25 mg) was added to a stirred solution of 5-(2-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide (94 mg, 0.15 mmol) in a mixture of MeOH (60 mL) and THF (10 mL) and stirred under hydrogen atmosphere. The reaction mixture was then stirred for 1 hrs at room temperature. The mixture was filtered over a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure. The crude was washed with ethyl acetate, filtered and dried to afford 36 mg (45% yield) of 5-(2-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 94.89%. 1H NMR (DMSO-d6): δ 13.2 (s, 1H), 10.4 (s, 1H), 7.9 (m, 2H), 7.5 (m, 2H), 6.9 (m, 3H), 4.1 (d, 2H), 3.4 (m, 6H), 3.1 (m, 2H).

Workup

  1. stirringThe reaction mixture was then stirred for 1 hrs at room temperature
  2. filtrationThe mixture was filtered over a bed of celite
  3. washThe celite was washed with MeOH
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washThe crude was washed with ethyl acetate
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-48715484efe3437193488a80c917367b
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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