4-Methylmorpholine → 4-(Aminosulfonyl)-N-((cis)-2-{[({[2-(trifluoromethyl)anilino]carbonyl)amino)acetyl]amino}cyclohexyl)benzamide

HRID 1825031

Reaktionsgleichung

Reaktionsgleichung von HRID 1825031
Br.[NH2:2][CH2:3][C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[NH:13][C:14](=[O:25])[C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1)=[O:5].CN1CCOCC1.[F:33][C:34]([F:45])([F:44])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]=[C:42]=[O:43].CCOC(C)=O>CN(C=O)C>[NH2:24][S:21]([C:18]1[CH:17]=[CH:16][C:15]([C:14]([NH:13][C@@H:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@@H:7]2[NH:6][C:4](=[O:5])[CH2:3][NH:2][C:42]([NH:41][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[C:34]([F:33])([F:44])[F:45])=[O:43])=[O:25])=[CH:20][CH:19]=1)(=[O:23])=[O:22]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 68830145N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide

Produkt 1

HCID 688266634-(Aminosulfonyl)-N-((cis)-2-{[({[2-(trifluoromethyl)anilino]carbonyl)amino)acetyl]amino}cyclohexyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. washthe solution was washed with 1N HCl
  2. dry with materialThe EtOAc was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

Quellen und Nachweise

ORD-Eintrag
ord-54120d5ba3b04eec8071e98d1cbc026e
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045521B2

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