Réaction #77834

ord-548d4312cc224e57adc1d3f3ab1ca060

Équation de réaction

CCOC(C)=O
EtOAc
CN1CCOCC1
4-methylmorpholine
O=C=Nc1ccccc1C(F)(F)F
2-trifluoromethylphenyl isocyanate
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
→
NS(=O)(=O)c1ccc(C(=O)N[C@@H]2CCCC[C@@H]2NC(=O)CNC(=O)Nc2ccccc2C(F)(F)F)cc1
benzamide
NS(=O)(=O)c1ccc(C(=O)N[C@@H]2CCCC[C@@H]2NC(=O)CNC(=O)Nc2ccccc2C(F)(F)F)cc1
4-(Aminosulfonyl)-N-((cis)-2-{[({[2-(trifluoromethyl)anilino]carbonyl}amino)acetyl]amino}cyclohexyl)benzamide

Réactifs

CCOC(C)=O
EtOAc
CN1CCOCC1
4-methylmorpholine
O=C=Nc1ccccc1C(F)(F)F
2-trifluoromethylphenyl isocyanate
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

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), (100 mg) was dissolved in DMF (3 mL) prior to the addition of 4-methylmorpholine (0.13 mL) and 2-trifluoromethylphenyl isocyanate (0.05 mL). 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 (50 mg). MS found: (M+Na)+=564.3.

Source

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