1353891-93-6

Basic information

• Product Name: N-((1R,2S)-1,2-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxybenzamido)ethyl)-3-oxopiperazine-1-carboxamide
• Synonyms: N-((1R,2S)-1,2-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxybenzamido)ethyl)-3-oxopiperazine-1-carboxamide
• CAS NO: 1353891-93-6
• Molecular Weight: 599.514
• Mol File: 1353891-93-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-((1R,2S)-1,2-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxybenzamido)ethyl)-3-oxopiperazine-1-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-((1R,2S)-1,2-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxybenzamido)ethyl)-3-oxopiperazine-1-carboxamide(1353891-93-6)
• EPA Substance Registry System: N-((1R,2S)-1,2-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxybenzamido)ethyl)-3-oxopiperazine-1-carboxamide(1353891-93-6)

Safety Data

• Hazardous Substances Data: 1353891-93-6(Hazardous Substances Data)

Upstream product

• 86212-34-2 (1R,2S)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine 
• 3848-36-0 4-chlorobenzaldoxime 
• 5625-67-2 2-Ketopiperazine 
• 1353891-90-3 tert-butyl (1R,2S)-1,2-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxybenzamido)ethylcarbamate 
• 530-62-1 1,1'-carbonyldiimidazole 
• 774225-25-1 N-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-4-chlorobenzylamine 
• 104-88-1 4-chlorobenzaldehyde 
• 1353891-92-5 N-((1S,2R)-2-amino-1,2-bis(4-chlorophenyl)ethyl)-2-isopropoxy-4-methoxybenzamide 
• 106-43-4 para-chlorotoluene 
• 1353891-52-7 tert-butyl ((1R,2S)-1,2-bis(4-chlorophenyl)-2-nitroethyl)carbamate 
• 1353891-88-9 tert-butyl ((1R,2S)-2-amino-1,2-bis(4-chlorophenyl)ethyl)carbamate 
• 1353891-99-2 isopropyl 2-isopropoxy-4-methoxybenzoate 
• 779342-75-5 tert-butyl 4-chlorobenzylidenecarbamate 
• 29559-24-8 4-chlorophenylnitromethane 

Downstream Products

• 548472-68-0 nutlin-3a 

Relevant articles and documents

Chiral synthesis method for producing cis-imidazoline compounds for pharmaceutical use

This invention provides a method for enantioselective synthesis of cis-imidazolines and related structures through chiral resolution. A chiral acid is used to separate enantiomeric precursors of the cis-imidazolines from a racemic mixture by selective cry

Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis -stilbene diamines: A platform for the preparation of single-enantiomer cis -imidazolines for protein-protein inhibition

The finding by scientists at Hoffmann-La Roche that cis-imidazolines could disrupt the protein-protein interaction between p53 and MDM2, thereby inducing apoptosis in cancer cells, raised considerable interest in this scaffold over the past decade. Initial routes to these small molecules (i.e., Nutlin-3) provided only the racemic form, with enantiomers being enriched by chromatographic separation using high-pressure liquid chromatography (HPLC) and a chiral stationary phase. Reported here is the first application of an enantioselective aza-Henry approach to nonsymmetric cis-stilbene diamines and cis-imidazolines. Two novel mono(amidine) organocatalysts (MAM) were discovered to provide high levels of enantioselection (>95% ee) across a broad range of substrate combinations. Furthermore, the versatility of the aza-Henry strategy for preparing nonsymmetric cis-imidazolines is illustrated by a comparison of the roles of aryl nitromethane and aryl aldimine in the key step, which revealed unique substrate electronic effects providing direction for aza-Henry substrate-catalyst matching. This method was used to prepare highly substituted cis-4,5-diaryl imidazolines that project unique aromatic rings, and these were evaluated for MDM2-p53 inhibition in a fluorescence polarization assay. The diversification of access to cis-stilbene diamine-derived imidazolines provided by this platform should streamline their further development as chemical tools for disrupting protein-protein interactions.

STEREOSELECTIVE METHODS, CATALYSTS AND INTERMEDIATES FOR THE SYNTHESIS OF (-)-NUTLIN-3 AND RELATED COMPOUNDS

The present invention provides methods and intermediates are provided for the preparation of (?)-Nutlin-3. Methods and intermediates are also provided for the enantioselective addition of aryl nitromethanes to aldimines. Bis(amidine) catalysts for the use