Benzoic Acid → 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,5-dioxo-imidazolidin-4-ylidenemethyl)-pyrazin-2-yl]-propionamide

HRID 719881ノート

反応式

HRID 719881 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH:22]=O)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[NH:30]1[CH2:36][C:34](=[O:35])[NH:33][C:31]1=[O:32].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH:22]=[C:36]3[C:34](=[O:35])[NH:33][C:31](=[O:32])[NH:30]3)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

参加物

6

反応物 4

HCID 243Benzoic AcidHCID 8082PiperidineHCID 10006HydantoinHCID 218973302-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-formyl-pyrazin-2-yl)-propionamide

生成物 1

HCID 674824182-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,5-dioxo-imidazolidin-4-ylidenemethyl)-pyrazin-2-yl]-propionamide収率 33%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
25 °C

実験手順

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-formyl-pyrazin-2-yl)-propionamide (prepared as in Example 18, 217 mg, 0.5 mmol), hydantoin (75 mg, 0.75 mmol), piperidine (10 μL, 0.10 mmol), and benzoic acid (6.1 mg, 0.05 mmol) in anhydrous ethanol (30 mL) was heated under reflux for 2 d. The reaction mixture was allowed to cool to 25° C. and then was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 10%–65% ethyl acetate/hexanes) afforded the 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,5-dioxo-imidazolidin-4-ylidenemethyl)-pyrazin-2-yl]-propionamide (84 mg, 33%) as a white solid: LC-MS m/e 518 (MH+).

後処理

  1. temperatureunder reflux for 2 d
  2. concentrationwas concentrated in vacuo

出典と根拠

ORDレコード
ord-031dcd7d4b9f4c91bc25113b77c57376
出典データセット
uspto-grants-2006_11
特許番号
US07132425B2

反応ノート

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