Reacción #80427

ord-358770dc8b62426c8b8107acc0b2f1eb

Ecuación de reacción

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

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroAfter the completion of the reaction
  2. 2
    workup.DISTILLATIONthe dimethylformamide was distilled away
  3. 3
    Extracciónthe residue was extracted with ethyl acetate
  4. 4
    SecadoThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. 5
    workup.DISTILLATIONthe solvent was distilled away
  6. 6
    Otroto give an oily product
  7. 7
    OtroThe oily product was purified by column chromatography

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05616581uspto-grants-1997_04