HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 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 58430863 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (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 | HCID 67389773 | 108.6% |
Reaction Steps
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]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08552205B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-1d35678b3e6d4380b7ea5ffc248097ec |
| Source note | uspto-grants-2013_10 |