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 1969676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969676
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]

Komponenten

4

Edukt 2

HCID 33557Sodium Azide2×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

Produkt 1

HCID 585579061-(-4-azido-2-ethylcyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazineAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-048e3ce42b5945b1881767ec8da1c8df
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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