Reaction #77835

ord-dcc707d7869046489fcea5627c8f95db

Reaction equation

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
Yield 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
Yield 29.4%

Reactants

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

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

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.v1Patent: US06706712B2uspto-grants-2004_03