Ethyl Acetate → 4-(Aminosulfonyl)-N-{(cis)-2-[({[(3-chlorophenyl)sulfonyl]amino)acetyl)amino]cyclohexyl}benzamide

HRID 49557

Reaktionsgleichung

Reaktionsgleichung von HRID 49557
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].[Cl:26][C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1.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][S:33]([C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([Cl:26])[CH:28]=2)(=[O:35])=[O:34])=[O:25])=[CH:20][CH:19]=1)(=[O:23])=[O:22]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 179093-Chlorobenzenesulphonyl chlorideHCID 68830145N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide

Produkt 1

HCID 688280684-(Aminosulfonyl)-N-{(cis)-2-[({[(3-chlorophenyl)sulfonyl]amino)acetyl)amino]cyclohexyl}benzamideAusbeute 29,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

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-dcc707d7869046489fcea5627c8f95db
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706712B2

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