Methanol → HCID 178507482, compound

HRID 1178135Notes

Reaction equation

HRID 1178135 reaction equation
[O:1]=[C:2]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:36])[F:35])[CH2:23][CH2:22]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[N+:18]([O-])=O)[NH:9][N:8]=1)=[O:6].CO>[Pd].C1COCC1>[O:1]=[C:2]([N:21]1[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:35])([F:37])[F:36])[CH2:25][CH2:26]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[NH2:18])[NH:9][N:8]=1)=[O:6]

Participants

5

Reactant 2

HCID 887MethanolHCID 178523539HCID 178523539, compound

Product 1

HCID 178507482HCID 178507482, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10% Pd/c (30 mg) was added to a stirred solution of 5-(2-Nitro-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide (160 mg, 0.3 mmol) in mixture of MeOH (60 mL) and THF (10 mL) and stirred under hydrogen atmosphere. The reaction mixture was then stirred for 1.5 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 40.3 mg (27% yield) of 5-(2-Amino-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 97.73%. 1H NMR (DMSO-d6): δ 13.6 (s, 1H), 8.6 (m, 1H), 7.6 (m, 4H), 7.5 (m, 1H), 7.4 (d, 1H), 7.3 (s, 1H), 7.0 (s, 1H), 6.5 (m, 4H), 6.2 (m, 2H), 5.1 (m, 1H), 4.2 (m, 3H), 3.6 (m, 4H), 3.4 (m, 2H), 3.2 (m, 2H).

Workup

  1. stirringThe reaction mixture was then stirred for 1.5 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-4bfc14f8eaf1456abbd876ef457afb9e
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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