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Sodium hydride → tert-butyl 2-(4-(dibenzylamino)-2-methylcyclopentyl)-2-oxoethyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate

HRID 1969848
ノート
印刷プレビュー

反応式

HRID 1969848 の反応式
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[H-].[Na+].Br[CH2:31][C:32]([CH:34]1[CH2:38][CH:37]([N:39]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:36][CH:35]1[CH3:54])=[O:33]>CN(C=O)C>[CH2:47]([N:39]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH:37]1[CH2:38][CH:34]([C:32](=[O:33])[CH2:31][N:20]([C:18]2[N:19]=[C:14]3[CH:13]=[CH:12][N:11]([S:1]([C:4]4[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=4)(=[O:3])=[O:2])[C:15]3=[N:16][CH:17]=2)[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[CH:35]([CH3:54])[CH2:36]1)[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 580097831,1-Dimethylethyl N-(5-((4-methylphenyl)sulfonyl)-5H-pyrrolo(2,3-b)pyrazin-2-yl)carbamateHCID 585571452-Bromo-1-(4-(dibenzylamino)-2-methylcyclopentyl)ethanone

生成物 1

HCID 58557498tert-butyl 2-(4-(dibenzylamino)-2-methylcyclopentyl)-2-oxoethyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate収率 97%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
3 回

反応条件

温度
0 °C

実験手順

A solution of tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate (0.59 g, 1.519 mmol, Example #3 Step E) in DMF (5 mL) was added dropwise to a suspension of NaH (60% dispersion in mineral oil, 0.058 g, 1.45 mmol) in DMF (5 mL), at about 0° C. The resulting mixture was stirred at about 0° C. for about 30 min and then added dropwise to a solution of 2-bromo-1-(4-(dibenzylamino)-2-methylcyclopentyl)ethanone (0.73 g, 1.8 mmol) in DMF (10 mL) at about 0° C. The resulting mixture was stirred at about 0° C. for about 1 h and the solvent was removed under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc (100 mL each). The organic phase was separated, dried over anhydrous MgSO4 and concd under reduced pressure to yield tert-butyl 2-(4-(dibenzylamino)-2-methylcyclopentyl)-2-oxoethyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate (1.04 g, 97%) as a yellow amorphous solid: LC/MS (Table 1, Method a) Rt=3.30 min; MS m/z 708 (M+H)+.

後処理

  1. stirringThe resulting mixture was stirred at about 0° C. for about 1 h
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc (100 mL each)
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous MgSO4 and concd under reduced pressure

出典と根拠

ORDレコード
ord-763f67188db84315a92aa4c0bce1d764
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426411B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート