Reaktion #1702116

ord-003dbe4c8da8459f95df39b55fd09568

Reaktionsgleichung

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
Ausbeute 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
Ausbeute 95.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe solvent was removed under vacuum
  2. 2
    workup.ADDITIONThe residue was treated with EtOAc and water
  3. 3
    TrocknenThe organic layer was dried over Na2SO4
  4. 4
    Filtrationfiltered
  5. 5
    Einengenconcentrated under vacuum

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08765727B2uspto-grants-2014_07