832096-89-6

Basic information

• Product Name: 3-Quinolinecarboxamide, 2-chloro-N-[(1S)-1-(2-iodophenyl)ethyl]-N-(1-methylethyl)-
• CAS NO: 832096-89-6
• Molecular Formula: C21H20ClIN2O
• Molecular Weight: 478.76
• Mol File: 832096-89-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Quinolinecarboxamide, 2-chloro-N-[(1S)-1-(2-iodophenyl)ethyl]-N-(1-methylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolinecarboxamide, 2-chloro-N-[(1S)-1-(2-iodophenyl)ethyl]-N-(1-methylethyl)-(832096-89-6)
• EPA Substance Registry System: 3-Quinolinecarboxamide, 2-chloro-N-[(1S)-1-(2-iodophenyl)ethyl]-N-(1-methylethyl)-(832096-89-6)

Safety Data

• Hazardous Substances Data: 832096-89-6(Hazardous Substances Data)

Upstream product

• 75815-80-4 (1S)-N-(1-methylethylidene)-1-phenylethylamine 
• 19302-32-0 (S)-N-isopropyl-1-phenylethylamine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 73776-25-7 2-chloro-3-quinolinecarboxylic acid 
• 612-62-4 2-Chloroquinoline 
• 136812-19-6 2-chloroquinoline-3-carbonyl chloride 
• 832096-87-4 (S)-N-[1-(2-iodophenyl)-ethyl]isopropylamine 

Relevant articles and documents

Preparation of axially chiral quinolinium salts related to NAD+ models: New investigations of these biomimetic models as 'chiral amide-transferring agents'

The general purpose of this work is to investigate the potential of biomimetic NAD+ models as 'nucleophile-transferring agents' with the ultimate motivation to develop new synthetic tools. This first report focuses on the preparation of an axially chiral quinolinium salt 8. A preliminary investigation of these NAD+ analogues as 'chiral amide-transferring agents' is reported herein. The synthesis of the desired quinolinium salt 8 was first attempted via a Friedlaender approach. Given the poor reproducibility of this first synthetic route, a second strategy making use of an intramolecular nickel-catalyzed coupling was developed with success, furnishing the quinolinium salt 8 in 12% overall yield. The potential of the quinolinium salt 8 as a 'chiral amide-transferring agent' was then investigated. Regioselective 1,4-addition of benzylamine and piperidine produced, respectively, adducts 18a and 18b with high diastereoselectivity (de >95%). The resulting 'chiral masked-amide' 18b was reacted with various activated aryl esters affording the corresponding atropisomeric amide 20 with modest atropenantioselectivity (ee = 2-20%).