Reaktion #80427

ord-358770dc8b62426c8b8107acc0b2f1eb

Reaktionsgleichung

Cc1c(SCCNCc2ccccc2)ccnc1CSc1nc2ccccc2[nH]1
2-((3-Methyl-4-(2-benzylaminoethylthio)pyridin-2-yl)methylthio)-1H-benzimidazole
COC(=O)CCl
methyl chloroacetate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COC(=O)CN(CCSc1ccnc(CSc2nc3ccccc3[nH]2)c1C)Cc1ccccc1
2-((3-methyl-4-(2-(N-benzyl-N-methoxycarbonylmethylamino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter the completion of the reaction
  2. 2
    workup.DISTILLATIONthe dimethylformamide was distilled away
  3. 3
    Extraktionthe residue was extracted with ethyl acetate
  4. 4
    TrocknenThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. 5
    workup.DISTILLATIONthe solvent was distilled away
  6. 6
    Sonstigeto give an oily product
  7. 7
    SonstigeThe oily product was purified by column chromatography

Vorschrift

2-((3-Methyl-4-(2-benzylaminoethylthio)pyridin-2-yl)methylthio)-1H-benzimidazole (2 g) was dissolved in dimethylformamide and reacted with methyl chloroacetate (0.45 ml) in the presence of potassium carbonate (0.71 g) at 50°-60° C. After the completion of the reaction, the dimethylformamide was distilled away and the residue was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to give an oily product. The oily product was purified by column chromatography to give 2-((3-methyl-4-(2-(N-benzyl-N-methoxycarbonylmethylamino)ethylthio)-2-pyridyl)methylthio)-1H-benzimidazole.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05616581uspto-grants-1997_04