HCID 178523540, compound → HCID 178523541, compound

HRID 1178136Notes

Reaction equation

HRID 1178136 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]=[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[CH2:27][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]=[CH:14][C:13]=2[OH:18])[NH:9][N:8]=1)=[O:6]

Participants

4

Reactant 1

HCID 178523540HCID 178523540, compound

Product 1

HCID 178523541HCID 178523541, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/c (20 mg) was added to a stirred solution of 5-(2-Benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide (103 mg, 0.17 mmol))(prepared by the method as described above) in MeOH (50 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 35.8 mg (41.3% yield) of 5-(2-Hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 93.92%. 1H NMR (DMSO): δ 13.1 (s, 1H), 10.3 (s, 1H), 8.2 (s, 1H), 7.74 (m, 2H), 7.62 (m, 2H), 7.52 (m, 1H), 7.16 (m, 1H), 7.04 (s, 1H), 6.96 (m, 1H), 6.86 (m, 1H), 4.1 (m, 2H), 3.55 (m, 4H), 3.4 (m, 2H), 3.2 (m, 2H).

Workup

  1. stirringThe reaction mixture was then stirred for 6 hrs
  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

Sources & evidence

ORD record
ord-a3657be2165b4a7aa369b66d34730093
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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