Reacción #1702116

ord-003dbe4c8da8459f95df39b55fd09568

Ecuación de reacción

Nc1cccc(CNc2nc(Cl)ncc2Cl)c1
N-(3-aminobenzyl)-2,5-dichloropyrimidin-4-amine
Cl
hydrogen chloride
CCN(CC)CC
triethylamine
O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1
m-nitrobenzenesulfonyl chloride
O=[N+]([O-])c1cccc(S(=O)(=O)Nc2cccc(CNc3nc(Cl)ncc3Cl)c2)c1
desired product
Rendimiento 95.0%
O=[N+]([O-])c1cccc(S(=O)(=O)Nc2cccc(CNc3nc(Cl)ncc3Cl)c2)c1
N-(3-{[(2,5-Dichloropyrimidin-4-yl)amino]methyl}phenyl)-3-nitrobenzenesulfonamide
Rendimiento 95.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe solvent was removed under vacuum
  2. 2
    workup.ADDITIONThe residue was treated with EtOAc and water
  3. 3
    SecadoThe organic layer was dried over Na2SO4
  4. 4
    Filtraciónfiltered
  5. 5
    Concentraciónconcentrated under vacuum

Procedimiento

To a mixture of N-(3-aminobenzyl)-2,5-dichloropyrimidin-4-amine.hydrogen chloride (0.20 g, 0.58 mmol) and triethylamine (0.32 mL, 2.3 mmol) in THF (3 mL) was added slowly m-nitrobenzenesulfonyl chloride (0.13 g, 0.58 mmol). The resulting mixture was stirred at rt for 2 hours and the solvent was removed under vacuum. The residue was treated with EtOAc and water. The organic layer was dried over Na2SO4, filtered, and concentrated under vacuum to provide the desired product (0.30 g, 95%). LCMS for C17H14Cl2N5O4S (M+H)+: m/z=453.9, 455.9.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08765727B2uspto-grants-2014_07