m-Chloroperbenzoic acid → 6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

HRID 1969653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969653
C(C1CC(SCC(F)(F)F)CC1[C:14]1[N:18]2[C:19]3[CH:25]=[CH:24][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:20]=3[N:21]=[CH:22][C:17]2=[N:16][N:15]=1)C.C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl>[CH3:31][Si:30]([CH3:33])([CH3:32])[CH2:29][CH2:28][O:27][CH2:26][N:23]1[C:20]2[N:21]=[CH:22][C:17]3[N:18]([CH:14]=[N:15][N:16]=3)[C:19]=2[CH:25]=[CH:24]1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 585574931-(2-ethyl-4-(2,2,2-trifluoroethylthio)cyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

Produkt 1

HCID 673772476-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazineAusbeute 164,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 1-(2-ethyl-4-(2,2,2-trifluoroethylthio)cyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.100 g, 0.200 mmol, Preparation #MMM.1) in DCM (0.667 mL) was added m-CPBA (0.090 g, 0.400 mmol). The reaction stirred at ambient temperature for about 0.5 h. The reaction mixture was quenched by the addition of saturated aqueous NaHCO3 (5 mL). The aqueous portion was extracted with DCM (2×10 mL). The combined organic layers were separated, dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-60% EtOAc in DCM to afford 1-2-ethyl-4-(2,2,2-trifluoroethylsulfonyl)cyclopentyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.095 g, 89%, 93% purity) as a clear oil: LC/MS (Table 1, Method a) Rt=2.63 min; MS m/z: 532 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was quenched by the addition of saturated aqueous NaHCO3 (5 mL)
  2. extractionThe aqueous portion was extracted with DCM (2×10 mL)
  3. customThe combined organic layers were separated
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with a gradient of 0-60% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-0bad1078d6d3409694996f9f6a61fb92
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

Notizen zur Reaktion

Wird geladen…