Reaktion #77835

ord-dcc707d7869046489fcea5627c8f95db

Reaktionsgleichung

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
Ausbeute 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
Ausbeute 29.4%

Edukte

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

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenthe solution was washed with 1N HCl
  2. 2
    TrocknenThe EtOAc was dried
  3. 3
    Filtrationfiltered
  4. 4
    Einengenconcentrated
  5. 5
    SonstigeReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06706712B2uspto-grants-2004_03