Sodium Azide → 1-(-4-azido-2-ethylcyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

HRID 1969676ノート

反応式

HRID 1969676 の反応式
CS(O[CH:6]1[CH2:10][CH:9]([C:11]2[N:15]3[C:16]4[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17]=4[N:18]=[CH:19][C:14]3=[N:13][N:12]=2)[CH:8]([CH2:31][CH3:32])[CH2:7]1)(=O)=O.[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C=O)C>[N:33]([CH:6]1[CH2:10][CH:9]([C:11]2[N:15]3[C:16]4[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17]=4[N:18]=[CH:19][C:14]3=[N:13][N:12]=2)[CH:8]([CH2:31][CH3:32])[CH2:7]1)=[N+:34]=[N-:35]

参加物

4

反応物 2

HCID 33557Sodium Azide2 回HCID 585576103-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl methanesulfonate

生成物 1

HCID 585579061-(-4-azido-2-ethylcyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine収率 89.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A round bottom flask was charged with 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl methanesulfonate (0.83 g, 1.7 mmol, Preparation #IIII.1) and DMF (7.0 mL). To the reaction flask was added sodium azide (0.56 g, 8.6 mmol). The mixture was stirred at ambient temperature for about 20 h. Another portion of sodium azide (0.056 g, 0.86 mmol) was added and the reaction was stirred for about 2 h. The reaction was partitioned between EtOAc (20 mL) and water (20 mL). The layers were separated and the organic solution was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 1-(-4-azido-2-ethylcyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.65 g, 88%) as a brown oil: LC/MS (Table 1, Method b) Rt=2.85 min; MS m/z: 427 (M+H)+.

後処理

  1. stirringthe reaction was stirred for about 2 h
  2. customThe reaction was partitioned between EtOAc (20 mL) and water (20 mL)
  3. customThe layers were separated
  4. dry with materialthe organic solution was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-048e3ce42b5945b1881767ec8da1c8df
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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