HCID 25164321, compound → HCID 25164723, compound

HRID 1177963Notes

Reaction equation

HRID 1177963 reaction equation
[N+:1]([C:4]1[CH:33]=[CH:32][C:7]([C:8]([NH:10][CH2:11][C:12](=[O:31])[N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:30])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[CH2:15][CH2:14]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][C:12](=[O:31])[N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:30])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[CH2:15][CH2:14]2)=[O:9])=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 25164321HCID 25164321, compound

Product 1

HCID 25164723HCID 25164723, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Nitro-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide (57 mg, 0.12 mmol) was dissolved in Methanol (1 mL). 10% Pd/C (10 mg) was added and the resulting mixture stirred for 4 hrs. The mixture was filtered over celite bed, and the filtrate was concentrated to afford 26 mg (49.1% yield) of 4-amino-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 97.4%, 1H NMR (CDCl3): δ 7.8-7.5 (m, 5H), 7.4-7.3 (d, 1H), 7.1-7.0 (s, 1H), 6.7-6.6 (d, 2H), 4.3-4.1 (m, 2H), 4.0 (bs, 3H), 3.8-3.5 (m, 5H), 3.4 (t, 1H), 3.2 (m, 2H).

Workup

  1. filtrationThe mixture was filtered over celite bed
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2c522057c0f74e77bbd47934a6bb3036
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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