Reaktion #77834

ord-548d4312cc224e57adc1d3f3ab1ca060

Reaktionsgleichung

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

Edukte

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

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), (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.

Quelle

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