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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 1969608
ノート
印刷プレビュー

反応式

HRID 1969608 の反応式
[H-].[Na+].[S:3]([N:13]1[C:17]2=[N:18][CH:19]=[C:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[N:21]=[C:16]2[CH:15]=[CH:14]1)([C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].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:22]([C:20]2[N:21]=[C:16]3[CH:15]=[CH:14][N:13]([S:3]([C:6]4[CH:7]=[CH:8][C:9]([CH3:10])=[CH:11][CH:12]=4)(=[O:5])=[O:4])[C:17]3=[N:18][CH:19]=2)[C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH:35]([CH3:54])[CH2:36]1)[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1
参加物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

実験手順

To a suspension of NaH (60% dispersion in mineral oil, 0.058 g, 1.45 mmol) in DMF (5 mL) was added 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) dropwise at about 0° C. The resulting mixture was stirred at this temperature for about 30 min and then added dropwise to a solution of 2-bromo-1-(4-(dibenzylamino)-2-methylcyclopentyl)ethanone (0.73 g, 1.823 mmol, Preparation #R.1) in DMF (10 mL). 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 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. dry with materialThe organic phase was dried over anhydrous MgSO4 and concd under reduced pressure

出典と根拠

ORDレコード
ord-899495df905e410491fe0ec5dbec5594
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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