Réaction #77835

ord-dcc707d7869046489fcea5627c8f95db

Équation de réaction

Br.NCC(=O)N[C@H]1CCCC[C@H]1NC(=O)c1ccc(S(N)(=O)=O)cc1
N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide
O=S(=O)(Cl)c1cccc(Cl)c1
3-chlorobenzenesulfonyl chloride
CCOC(C)=O
EtOAc
→
NS(=O)(=O)c1ccc(C(=O)N[C@@H]2CCCC[C@@H]2NC(=O)CNS(=O)(=O)c2cccc(Cl)c2)cc1
benzamide
Rendement 29.4%
NS(=O)(=O)c1ccc(C(=O)N[C@@H]2CCCC[C@@H]2NC(=O)CNS(=O)(=O)c2cccc(Cl)c2)cc1
4-(Aminosulfonyl)-N-{(cis)-2-[({[(3-chlorophenyl)sulfonyl]amino}acetyl)amino]cyclohexyl}benzamide
Rendement 29.4%

Réactifs

Br.NCC(=O)N[C@H]1CCCC[C@H]1NC(=O)c1ccc(S(N)(=O)=O)cc1
N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide
O=S(=O)(Cl)c1cccc(Cl)c1
3-chlorobenzenesulfonyl chloride
CCOC(C)=O
EtOAc

Réactifs

Aucun

Solvants

CN(C)C=O
DMF

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Lavagethe solution was washed with 1N HCl
  2. 2
    SéchageThe EtOAc was dried
  3. 3
    Filtrationfiltered
  4. 4
    Concentrationconcentrated
  5. 5
    AutreReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

Mode opératoire

N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide, (61b), (70 mg) was dissolved in DMF (2.5 mL) prior to the addition of 3-chlorobenzenesulfonyl chloride (51 mg). After stirring overnight, EtOAc was added and the solution was washed with 1N HCl. The EtOAc was dried, filtered, and concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the title benzamide (25 mg). MS found: (M+H)+=530.1.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06706712B2uspto-grants-2004_03