تفاعل #1702116

ord-003dbe4c8da8459f95df39b55fd09568

معادلة التفاعل

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
المردود 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
المردود 95.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىthe solvent was removed under vacuum
  2. 2
    workup.ADDITIONThe residue was treated with EtOAc and water
  3. 3
    تجفيفThe organic layer was dried over Na2SO4
  4. 4
    ترشيحfiltered
  5. 5
    تركيزconcentrated under vacuum

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08765727B2uspto-grants-2014_07