Chloride → Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate

HRID 2110187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110187
[Cl-].Cl.[CH2:3]([N:10]([CH2:14][C:15]1[N:16]=[CH:17][NH:18][C:19]=1[C:20]([O:22][CH3:23])=[O:21])[CH2:11][CH2:12]Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(#N)C>[CH2:3]([N:10]1[CH2:11][CH2:12][N:16]2[CH:17]=[N:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:15]2[CH2:14]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 312ChlorideHCID 178499150HCID 178499150, Verbindung

Produkt 1

HCID 57635262Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylateAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The chloride, Intermediate 1E (0.97 g, 3.15 mmol) was dissolved in acetonitrile (30 mL) and TEA (1.77 mL, 12.62 mmol) was added drop wise. The resulting mixture was stirred at 80° C. under nitrogen overnight. The mixture was allowed to cool, was filtered and the filtrate was concentrated. The residue was partitioned between DCM and saturated NaHCO3 solution and the phases were separated. The aqueous phase was further extracted with DCM and combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated. The crude residue was purified using normal phase chromatography, eluting with a 0-40% methanol/DCM gradient to provide product Intermediate 1F (0.58 g, 66%) as a brown solid.

Aufarbeitung

  1. temperatureto cool
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was partitioned between DCM and saturated NaHCO3 solution
  5. customthe phases were separated
  6. extractionThe aqueous phase was further extracted with DCM
  7. dry with materialwere dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was purified
  11. washeluting with a 0-40% methanol/DCM gradient

Quellen und Nachweise

ORD-Eintrag
ord-b2d7c6eeb16a44198a3e1d94415c0a02
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517874B2

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