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 → HCID 67389773, compound

HRID 1040559Notes

Reaction equation

HRID 1040559 reaction equation
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]

Participants

5

Reactant 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

Product 1

HCID 67389773HCID 67389773, compoundYield 108.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-1d35678b3e6d4380b7ea5ffc248097ec
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

Loading…