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 1177992ノート

反応式

HRID 1177992 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f00a92a61de946a6af3e03710d48bbe9
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

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