N'-{1-[(1-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarbonyl)-amino]-cyclopropanecarbonyl}-hydrazinecarboxylic acid tert-butyl ester → (R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo-[1,2-a]imidazole-3-carboxylic acid [1-(1-hydrazinocarbonyl-cyclopropylcarbamoyl)-cyclopropyl]-amide hydrochloride

HRID 1040559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040559
C(OC([NH:8][NH:9][C:10]([C:12]1([NH:15][C:16]([C:18]2([NH:21][C:22]([C:24]3[N:28]4[C@@:29]([CH2:42][C:43]5[CH:48]=[CH:47][C:46]([C:49]#[N:50])=[CH:45][CH:44]=5)([CH3:41])[C:30](=[O:40])[N:31]([C:32]5[CH:37]=[C:36]([Cl:38])[CH:35]=[C:34]([Cl:39])[CH:33]=5)[C:27]4=[N:26][CH:25]=3)=[O:23])[CH2:20][CH2:19]2)=[O:17])[CH2:14][CH2:13]1)=[O:11])=O)(C)(C)C>Cl.O1CCOCC1.CCOCC>[ClH:38].[NH:9]([C:10]([C:12]1([NH:15][C:16]([C:18]2([NH:21][C:22]([C:24]3[N:28]4[C@@:29]([CH2:42][C:43]5[CH:44]=[CH:45][C:46]([C:49]#[N:50])=[CH:47][CH:48]=5)([CH3:41])[C:30](=[O:40])[N:31]([C:32]5[CH:37]=[C:36]([Cl:38])[CH:35]=[C:34]([Cl:39])[CH:33]=5)[C:27]4=[N:26][CH:25]=3)=[O:23])[CH2:20][CH2:19]2)=[O:17])[CH2:14][CH2:13]1)=[O:11])[NH2:8]

Komponenten

5

Edukt 1

HCID 58430863N'-{1-[(1-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarbonyl)-amino]-cyclopropanecarbonyl}-hydrazinecarboxylic acid tert-butyl ester

Produkt 1

HCID 67389773(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo-[1,2-a]imidazole-3-carboxylic acid [1-(1-hydrazinocarbonyl-cyclopropylcarbamoyl)-cyclopropyl]-amide hydrochlorideAusbeute 108,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N′-{1-[(1-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarbonyl)-amino]-cyclopropanecarbonyl}-hydrazinecarboxylic acid tert-butyl ester (0.30 g, 0.42 mmol) was dissolved in 4 N HCl in dioxane (3 mL) and allowed to stir at room temperature for 40 min. The resulting white suspension was diluted with Et2O and the precipitate was collected by filtration. The solid was washed twice with Et2O to give (R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo-[1,2-a]imidazole-3-carboxylic acid [1-(1-hydrazinocarbonyl-cyclopropylcarbamoyl)-cyclopropyl]-amide hydrochloride (0.15 g, 52%) as a white powder, m/z 621.7 [M+1]+.

Aufarbeitung

  1. filtrationthe precipitate was collected by filtration
  2. washThe solid was washed twice with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-1d35678b3e6d4380b7ea5ffc248097ec
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552205B2

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