HCID 178523543, compound → HCID 178523542, compound

HRID 1178133Notes

Reaction equation

HRID 1178133 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)[NH:9][N:8]=1)=[O:6]>CO.C(Cl)Cl.[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)[NH:9][N:8]=1)=[O:6]

Participants

5

Reactant 1

HCID 178523543HCID 178523543, compound

Product 1

HCID 178523542HCID 178523542, compoundYield 23.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

10% Pd/c (30 mg) was added to a stirred solution of 5-(3-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide (120.3 mg, 0.2 mmol) in a mixture of MeOH (15 mL) and DCM (10 mL) and stirred under hydrogen atmosphere. The reaction mixture was then stirred overnight 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 recrystallized from a mixture of ethyl acetate and methanol to afford 23.9 mg (23.7% yield) of 5-(3-Hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 98.15%. 1H NMR (DMSO-d6): δ 13.6 (s, 1H), 9.6 (s, 1H), 8.6 (d, 1H), 8.1 (s, 1H), 7.6 (m, 3H), 7.5 (m, 1H), 7.1 (m, 3H), 7.0 (s, 1H), 6.7 (d, 1H), 4.1 (d, 2H), 3.6 (m, 2H), 3.5 (m, 2H), 3.4 (m, 2H), 3.1 (m, 2H).

Workup

  1. stirringThe reaction mixture was then stirred overnight 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. customThe crude was recrystallized from a mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-3a77469170304cb69d17ca5b6a28ea19
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…