1009119-65-6

Basic information

• Product Name: N,N'-[[1,1'-Biphenyl]-4,4'-diylbis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]biscarbamic acid dimethyl ester hydrochloride
• Synonyms: BMS 790052;N,N'-[[1,1'-Biphenyl]-4,4'-diylbis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]biscarbamic acid dimethyl ester hydrochloride;BMS-790052 (dihydrochloride);BMS790052 HCl;Daclatasvir dihydrochloride;BMS-790052 2HCl;DACLATASVIR(2HCl);Daclatasvir HCL
• CAS NO: 1009119-65-6
• Molecular Formula: C40H50N8O6.2(HCl)
• Molecular Weight: 767.27242
• EINECS: 1592732-453-0
• Product Categories: Inhibitors
• Mol File: 1009119-65-6.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: N,N'-[[1,1'-Biphenyl]-4,4'-diylbis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]biscarbamic acid dimethyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-[[1,1'-Biphenyl]-4,4'-diylbis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]biscarbamic acid dimethyl ester hydrochloride(1009119-65-6)
• EPA Substance Registry System: N,N'-[[1,1'-Biphenyl]-4,4'-diylbis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]biscarbamic acid dimethyl ester hydrochloride(1009119-65-6)

Safety Data

• Hazardous Substances Data: 1009119-65-6(Hazardous Substances Data)

Usage

Description

N,N'-[[1,1'-Biphenyl]-4,4'-diylbis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]biscarbamic acid dimethyl ester hydrochloride is a complex organic compound with a unique structure that features a biphenyl core connected to imidazole and pyrrolidine rings through carbamate linkages. N,N'-[[1,1'-Biphenyl]-4,4'-diylbis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]biscarbamic acid dimethyl ester hydrochloride is characterized by its hydrochloride salt form, which may contribute to its solubility and stability in certain conditions.

Uses

There is no specific information provided in the materials about the uses of N,N'-[[1,1'-Biphenyl]-4,4'-diylbis[1H-imidazole-5,2-diyl-(2S)-2,1-pyrrolidinediyl[(1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl]]]biscarbamic acid dimethyl ester hydrochloride. However, given its structural features, it may have potential applications in various fields such as pharmaceuticals, materials science, or as a chemical intermediate. Further research and development would be required to explore and confirm its specific uses and benefits in different industries.

Synthesis

Bromination of commercial 4,40-diacetylbiphenyl (58) gave 4,40-bis(bromoacetyl)biphenyl 59 in 82% yield. Alkylation of NBoc- L-proline (60) with 59 gave diester 61 which was treated with ammonium acetate to effect cyclization of the bis-ketoester to provide bis-imidazole 62 in 63% yield for the two steps. Acidic removal of the Boc protecting groups followed by recrystallization provided bis-pyrrolidine 63 in high yield. Acylation of 63 with N-(methoxycarbonyl)- L-valine (64) using N-(3-dimethylaminopropyl)-N0-ethylcarbodiimide (EDC) and 1-hydroxybenxotriazole hydrate (HOBT) provided declatasvir. The dihydrochloride salt was prepared and treated with Cuno Zet Carbon ? followed by crystallization from acetone to give daclatasvir dihydrochloride (IX) in 74% yield.

Mode of action

Daclatasvir is an inhibitor of nonstructural protein 5A (NS5A), a multifunctional protein that is an essential component of the HCV replication complex. Daclatasvir binds to the N-terminus of NS5A and inhibits both viral RNA replication and virion assembly.