Reacción #487543

ord-58ee575fb1c44abf9b534308bd2b810c

Ecuación de reacción

FC(F)(F)COc1nc(Cl)nc(Cl)n1
2,4-dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine
COC(=O)c1ccc(N)cc1OCCCCl
methyl 4-amino-2-(3-chloropropoxy)benzoate
COC(=O)c1ccc(Nc2nc(Cl)nc(OCC(F)(F)F)n2)cc1OCCCCl
methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe organic layer was collected
  2. 2
    Secadodried over sodium sulfate
  3. 3
    Concentraciónconcentrated under vacuum
  4. 4
    OtroThe crude product was purified by silica gel chromatography
  5. 5
    OtroThe product fractions were collected
  6. 6
    Concentraciónconcentrated under vacuum

Procedimiento

To a solution of 2,4-dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine (770 mg, 2.79 mmol) in THF (10 mL) was added methyl 4-amino-2-(3-chloropropoxy)benzoate (681 mg, 2.79 mmol) and Hunig'sBase (1.464 mL, 8.38 mmol). The resulting mixture was stirred for 16 h. The reaction was diluted with DCM and water. The organic layer was collected and dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by silica gel chromatography using 20-40% EtOAc/Hexanes. The product fractions were collected and concentrated under vacuum to give methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate as a solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08741884B2uspto-grants-2014_06