Benzoic acid, 2-amino-5-iodo- → benzamide 2-amino-N-{2-[((cis)-2-{[4-(aminosulfonyl)benzoyl]amino}cyclohexyl)amino]-2-oxoethyl}-5-iodobenzamide

HRID 1825030

Reaktionsgleichung

Reaktionsgleichung von HRID 1825030
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].C(N(C(C)C)CC)(C)C.[NH2:35][C:36]1[CH:44]=[CH:43][C:42]([I:45])=[CH:41][C:37]=1[C:38](O)=[O:39].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[NH2:35][C:36]1[CH:44]=[CH:43][C:42]([I:45])=[CH:41][C:37]=1[C:38]([NH: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:16]=[CH:17][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:19][CH:20]=1)=[O:5])=[O:39].[C:14]([NH2:13])(=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

8

Edukt 5

HCID 72911Benzoic acid, 2-amino-5-iodo-HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 68830145N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide

Produkt 1

HCID 68830524benzamide 2-amino-N-{2-[((cis)-2-{[4-(aminosulfonyl)benzoyl]amino}cyclohexyl)amino]-2-oxoethyl}-5-iodobenzamideAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The above material, (61b), N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide (59 mg) was dissolved in DMF (1 mL). After cooling to 0° C., diisopropylethylamine (0.1 mL) and 2-amino-5-iodobenzoic acid (43 mg) were added. BOP Reagent (72 mg) was added, and the mixture was stirred overnight. EtOAc was added along with NaHCO3 solution. The EtOAc was dried (MgSO4), filtered, and concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the title benzamide 2-amino-N-{2-[((cis)-2-{[4-(aminosulfonyl)benzoyl]amino}cyclohexyl)amino]-2-oxoethyl}-5-iodobenzamide (6 mg). MS found: (M+Na)+=622.2.

Aufarbeitung

  1. dry with materialThe EtOAc was dried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

Quellen und Nachweise

ORD-Eintrag
ord-e1fb2ba136be409780e62429b2ad483f
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045521B2

Verknüpfte Notizen

Wird geladen…