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 1177992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177992
[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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 59559665Biphenyl-4-carboxylic acid {2-[4-(5-amino-2-bromo-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amideAusbeute 40,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f00a92a61de946a6af3e03710d48bbe9
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842696B2

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