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

HRID 719882ノート

反応式

HRID 719882 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH:22]=[C:23]3[C:27](=[O:28])[NH:26][C:25](=[O:29])[NH:24]3)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]>C(O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:30][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH2:22][CH:23]3[C:27](=[O:28])[NH:26][C:25](=[O:29])[NH:24]3)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

参加物

4

反応物 1

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

生成物 1

HCID 100296442-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,5-dioxo-imidazolidin-4-ylmethyl)-pyrazin-2-yl]-propionamide収率 15.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒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-(2,5-dioxo-imidazolidin-4-ylidenemethyl)-pyrazin-2-yl]-propionamide (130 mg, 0.25 mmol) in ethanol (5 mL) was treated with 10% palladium on activated carbon (260 mg). The reaction mixture was stirred under hydrogen (65 psi) at 25° C. for 2 d. The catalyst was then filtered off through a pad of celite, and the celite pad was washed well with ethanol. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 80%–100% ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,5-dioxo-imidazolidin-4-ylmethyl)-pyrazin-2-yl]-propionamide (20 mg, 15%) as a white solid: LC-MS m/e 520 (MH+).

後処理

  1. filtrationThe catalyst was then filtered off through a pad of celite
  2. washthe celite pad was washed well with ethanol
  3. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-1270ea38081349aaa1361bbc8440ee26
出典データセット
uspto-grants-2006_11
特許番号
US07132425B2

反応ノート

読み込み中…