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 1969676노트

반응식

HRID 1969676 반응식
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]

참가 물질

4

반응물 2

HCID 33557Sodium Azide2회HCID 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-048e3ce42b5945b1881767ec8da1c8df
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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