210288-67-8

Basic information

• Product Name: (2S)-7-IODO-4-METHYL-3-OXO-2,3,4,5-TETRAHYDRO-1H-1,4-BENZODIAZEPIN-2-YL]ACETIC ACID
• Synonyms: (2S)-7-IODO-4-METHYL-3-OXO-2,3,4,5-TETRAHYDRO-1H-1,4-BENZODIAZEPIN-2-YL]ACETIC ACID
• CAS NO: 210288-67-8
• Molecular Formula: C12H13IN2O3
• Molecular Weight: 360.14769
• Mol File: 210288-67-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S)-7-IODO-4-METHYL-3-OXO-2,3,4,5-TETRAHYDRO-1H-1,4-BENZODIAZEPIN-2-YL]ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-7-IODO-4-METHYL-3-OXO-2,3,4,5-TETRAHYDRO-1H-1,4-BENZODIAZEPIN-2-YL]ACETIC ACID(210288-67-8)
• EPA Substance Registry System: (2S)-7-IODO-4-METHYL-3-OXO-2,3,4,5-TETRAHYDRO-1H-1,4-BENZODIAZEPIN-2-YL]ACETIC ACID(210288-67-8)

Safety Data

• Hazardous Substances Data: 210288-67-8(Hazardous Substances Data)

Usage

General Description

(2S)-7-Iodo-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-yl]acetic acid, also known as S-IMAA, is a chemical compound that belongs to the class of benzodiazepine derivatives. It is a potent and selective GABA-A receptor agonist, which means it can bind to and activate the GABA-A receptors in the brain, leading to anxiolytic, sedative, and muscle-relaxant effects. (2S)-7-IODO-4-METHYL-3-OXO-2,3,4,5-TETRAHYDRO-1H-1,4-BENZODIAZEPIN-2-YL]ACETIC ACID has been studied for its potential as a therapeutic agent for the treatment of anxiety, insomnia, and other neurological disorders. Research on this compound is ongoing, and it continues to be of interest in the field of pharmacology and neuroscience.

Upstream product

• 363138-96-9 (E)-2-[Methyl-(2-nitro-benzyl)-amino]-but-2-enedioic acid dimethyl ester 
• 193077-87-1 (4-methyl-3-oxo-2,3,4-tetrahydro-1H-benzo[e][1,4]diazepin-2-yl)-acetic acid methyl ester 
• 163915-96-6 (2-nitrophenyl)methyl methanesulfonate 
• 154915-16-9 methyl 2-(2-methoxy-2-oxoethyl)-3-methyl-1,2,3,4-tetrahydroquinazoline-2-carboxylate 
• 56222-08-3 (2-nitrobenzyl)methylamine 
• 612-25-9 2-Nitrobenzyl alcohol 
• 210288-68-9 (2S)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid 

Downstream Products

• 171049-14-2 lotrafiban 

Relevant articles and documents

The development of a manufacturing route for the GPIIb/IIIa receptor antagonist SB-214857-A. Part 2: Conversion of the key intermediate SB-235349 to SB-214857-A

The process development to the manufacturing route to (2S)-7-([4,4′ -bipiperidin]-1-ylcarbonyl)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1, 4-benzodiazepine-2-acetic acid hydrochloride (SB-214857-A, lotrafiban) is described. The starting point is the previously reported intermediate (2RS)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid methyl ester. The first stage is a lipase-catalysed resolution of the racemic ester to (2S)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid and subsequent iodination using a pyridine iodine monochloride complex to give (2S)-2,3,4,5-tetrahydro-7-iodo-4-methyl-3-oxo-1H-1,4-benzodiazepine-2- acetic acid. The unreacted (R)-enantiomer of the starting ester is recovered and recycled to the racemate by treatment with sodium methoxide. The next stage describes the palladium-catalysed aminocarbonylation of the aryl iodide with 4,4′-pyridylpiperidine to give (2S)-2,3,4,5-tetrahydro-4-methyl-3-oxo-7-[[4-(4-pyridinyl)-1-piperidinyl] carbonyl]-1H-1,4-benzodiazepine-2-acetic acid dihydrate. The third stage is the hydrogenation of the pyridine subunit over palladium on charcoal to obtain the zwitterionic (2S)-7-([4,4′ -bipiperidin]-1-ylcarbonyl)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1, 4-benzodiazepine-2-acetic acid hexahydrate. The final stage is the formation of the hydrochloride salt to afford the drug substance.