HCID 178499149, Verbindung → Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate

HRID 1808349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808349
[CH2:1]([N:8]([CH2:12][C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH2:9][CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C>[CH2:1]([N:8]1[CH2:9][CH2:10][N:14]2[CH:15]=[N:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:13]2[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 178499149HCID 178499149, Verbindung

Produkt 1

HCID 57635262Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

TEA (28.66 mmol, 4 equiv.) was added at 0° C. to a solution of methyl 4-((benzyl(2-chloroethyl)amino)methyl)-1H-imidazole-5-carboxylate (7.16 mmol, 1 equiv.) in acetonitrile (50 ml). The resulting mixture was heated for 16 h at 80° C. It was then cooled and filtered, and the filtrate was concentrated in vacuo. The crude product was taken up in DCM and sat. sodium hydrogen carbonate solution, and the organic phase was dried and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, 5% MeOH in DCM), and the desired product was thus obtained in the form of a brown solid. Yield: 64%

Aufarbeitung

  1. temperatureIt was then cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dry with materialsat. sodium hydrogen carbonate solution, and the organic phase was dried
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified by column chromatography (silica gel, 5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-4a6b0c6c89a340e8846055e876062f55
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357717B2

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