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1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine → 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

HRID 1969883
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1969883
[CH2:1]([CH:3]1[CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH:4]1[C:12]1[N:16]2[C:17]3[CH:23]=[CH:22][N:21](S(C4C=CC(C)=CC=4)(=O)=O)[C:18]=3[N:19]=[CH:20][C:15]2=[N:14][N:13]=1)[CH3:2]>O1CCOCC1.[OH-].[Na+]>[CH2:1]([CH:3]1[CH2:11][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:5][CH:4]1[C:12]1[N:16]2[C:17]3[CH:23]=[CH:22][NH:21][C:18]=3[N:19]=[CH:20][C:15]2=[N:14][N:13]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 585572181-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

Produkt 1

HCID 1360092531-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazineAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14798Sodium HydroxideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To the solution of 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (3.76 g, 8.04 mmol) in 1,4-dioxane (55 mL), aqueous sodium hydroxide solution (2N, 12 mL) was added and the reaction mixture was heated at about 60° C. for about 90 min. The solvent was removed and the residue partitioned between saturated solution of ammonium chloride in water and EtOAc (75 mL each). The aqueous phase was further washed with EtOAc (60 mL); the combined organic extracts were washed with brine (65 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to yield a brown solid. The solid was triturated in ether (20 mL) and the precipitate was collected by filtration and dried to yield 1-(8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (2.22 g, 88%) as a beige solid. LC/MS (Table 1, Method a) Rt=1.71 min; MS m/z: 314 (M+H)+.

Aufarbeitung

  1. customThe solvent was removed
  2. customthe residue partitioned between saturated solution of ammonium chloride in water and EtOAc (75 mL each)
  3. washThe aqueous phase was further washed with EtOAc (60 mL)
  4. washthe combined organic extracts were washed with brine (65 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown solid
  9. customThe solid was triturated in ether (20 mL)
  10. filtrationthe precipitate was collected by filtration
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e236737de73943899a7656d037f8d8ea
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08426411B2

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