Biphenyl-4-carboxylic acid {2-[4-(2-bromo-5-nitro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide → Biphenyl-4-carboxylic acid {2-[4-(5-amino-2-bromo-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide

HRID 1177992Notes

Reaction equation

HRID 1177992 reaction equation
[Br:1][C:2]1[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:29])[CH2:13][NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[O:16])[CH2:8][CH2:7]1)=[O:5]>CO.[Pd]>[NH2:34][C:31]1[CH:32]=[CH:33][C:2]([Br:1])=[C:3]([CH:30]=1)[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:29])[CH2:13][NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)=[O:16])[CH2:8][CH2:7]1)=[O:5]

Participants

4

Reactant 1

HCID 59559617Biphenyl-4-carboxylic acid {2-[4-(2-bromo-5-nitro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide

Product 1

HCID 59559665Biphenyl-4-carboxylic acid {2-[4-(5-amino-2-bromo-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amideYield 40.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (60 mg) was added to a stirred solution of biphenyl-4-carboxylic acid {2-[4-(2-bromo-5-nitro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide (120 mg, 2.4 mmol) in methanol (10 mL) and the mixture was stirred under an atmosphere of hydrogen with pressure overnight. The mixture was then filtered over celite and the filtrate concentrated to afford 46 mg (40.7%) of biphenyl-4-carboxylic acid {2-[4-(5-amino-2-bromo-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS: 95.6%, 1H NMR (CDCl3): δ 7.9 (m, 2H), 7.6 (m, 4H), 7.4 (m, 4H), 6.8 (m, 2H), 4.2 (m, 2H), 4.0 (m, 11H), 3.6 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-f00a92a61de946a6af3e03710d48bbe9
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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