923604-56-2

Basic information

• Product Name: (1R,2S)-2-Ethenyl-1-[[[(1R,2R,4R)-2-[(5-hexen-1-ylmethylamino)carbonyl]-4-[[7-methoxy-8-methyl-2-[4-Isopropyl-thiazol-2-yl]-quinolin-4-yl]oxy]cyclopentyl]carbonyl]amino]cyclopropane-carboxylic acid ethyl este
• Synonyms: (1R,2S)-2-Ethenyl-1-[[[(1R,2R,4R)-2-[(5-hexen-1-ylmethylamino)carbonyl]-4-[[7-methoxy-8-methyl-2-[4-Isopropyl-thiazol-2-yl]-quinolin-4-yl]oxy]cyclopentyl]carbonyl]amino]cyclopropane-carboxylic acid ethyl este;(1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate;(1R,2S)-2-Ethenyl-1-[[[(1R,2R,4R)-2-[(5-hexen-1-ylmethylamino)carbonyl]-4-[[7-methoxy-8-methyl-2-[4-Isopropyl-thiazol-2-yl]-quinolin-4-yl]oxy]cyclopentyl]carbonyl]amino]cyclopropane-carboxylic;(1R,2S)-2-Ethenyl-1-[[[(1R,2R,4R)-2-[(5-hexen-1-ylmethylamino)carbonyl]-4-[[7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]cyclopentyl]carbonyl]amino]cyclopropanecarboxylic acid ethyl ester
• CAS NO: 923604-56-2
• Molecular Formula: C₃₉H₅₀N₄O₆S
• Molecular Weight: 702.9
• Mol File: 923604-56-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,2S)-2-Ethenyl-1-[[[(1R,2R,4R)-2-[(5-hexen-1-ylmethylamino)carbonyl]-4-[[7-methoxy-8-methyl-2-[4-Isopropyl-thiazol-2-yl]-quinolin-4-yl]oxy]cyclopentyl]carbonyl]amino]cyclopropane-carboxylic acid ethyl este(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-Ethenyl-1-[[[(1R,2R,4R)-2-[(5-hexen-1-ylmethylamino)carbonyl]-4-[[7-methoxy-8-methyl-2-[4-Isopropyl-thiazol-2-yl]-quinolin-4-yl]oxy]cyclopentyl]carbonyl]amino]cyclopropane-carboxylic acid ethyl este(923604-56-2)
• EPA Substance Registry System: (1R,2S)-2-Ethenyl-1-[[[(1R,2R,4R)-2-[(5-hexen-1-ylmethylamino)carbonyl]-4-[[7-methoxy-8-methyl-2-[4-Isopropyl-thiazol-2-yl]-quinolin-4-yl]oxy]cyclopentyl]carbonyl]amino]cyclopropane-carboxylic acid ethyl este(923604-56-2)

Safety Data

• Hazardous Substances Data: 923604-56-2(Hazardous Substances Data)

Usage

General Description

"(1R,2S)-2-Ethenyl-1-[[[(1R,2R,4R)-2-[(5-hexen-1-ylmethylamino)carbonyl]-4-[[7-methoxy-8-methyl-2-[4-Isopropyl-thiazol-2-yl]-quinolin-4-yl]oxy]cyclopentyl]carbonyl]amino]cyclopropane-carboxylic acid ethyl ester" is a complex chemical compound that includes a variety of functional groups and substituents. It contains a cyclopropane carboxylic acid core and a cyclopentyl carbonyl amino group, as well as an ethyl ester side chain. The molecule also contains a number of heterocyclic compounds like thiazole and quinoline, and functional groups such as an ethenyl and a methoxy group. The chemical structure indicates potential pharmaceutical and biological activity due to its intricate and unique composition.

Upstream product

• 922727-93-3 (1R,2S)-1-{[(1R,2R,4S)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester 
• 923289-21-8 8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol 
• 746657-36-3 (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate 
• 862259-02-7 trans-(3R,4R)-3,4-bis(methoxycarbonyl)cyclopentanol 
• 55863-02-0 N-methylhex-5-en-1-amine 
• 1333964-94-5 (1R,2R,4R)-2-[[(1R,2S)-1-(ethoxycarbonyl)-2-vinyl-cyclopropyl]carbamoyl]-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]cyclopentanecarboxylic acid 
• 1703-61-3 racemic trans-cyclopentanone-3,4-dicarboxylic acid 
• 35079-19-7 trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane 
• 1333964-81-0 benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate 
• 1333964-84-3 benzyl methyl (1R,2R,4S)-4-([2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy)-1,2-cyclopentanedicarboxylate 
• 1333964-85-4 (1R,2R,4R)-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]-2-(methoxycarbonyl)cyclopentanecarboxylic acid 
• 1333964-92-3 methyl (1R,2R,4R)-2-[[(1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl]carbamoyl]-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]cyclopentanecarboxylate 
• 862174-98-9 (1R,4R,5R)-N-(hex-5-en-1-yl)-N-methyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide 
• 1042695-84-0 methyl (1R,2R,4R)-2-[5-hexen-1-yl-(methyl)carbamoyl]-4-hydroxycyclopentanecarboxylate 

Downstream Products

• 923604-57-3 2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydro-2-[[7-methoxy-8-methyl-2-[4-10(1-methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-methyl-4,14-dioxo-(2R,3aR,10Z,11aS,2aR,14aR)-cyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid ethyl ester 
• 923604-58-4 (2R,3aR,10Z,11aS,12aR,14aR)-2-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)-5-methyl-4,14-dioxo-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid 
• 923604-59-5 simeprevir 

Relevant articles and documents

Ring-Closing Metathesis on Commercial Scale: Synthesis of HCV Protease Inhibitor Simeprevir

The key macrocyclization step in the synthesis of simeprevir, a hepatitis C virus (HCV) antiviral drug, was studied. N-Boc substitution on the diene precursor changes the site of insertion of the metathesis catalyst and, consequently, the kinetic model of the ring closing metathesis (RCM), enabling a further increase in the macrocyclization efficiency under simulated high dilution (SHD) conditions. NMR of the inserted species of both first and second generation RCM catalysts are reported and discussed.

PROCESSES AND INTERMEDIATES FOR PREPARING A MACROCYCLIC PROTEASE INHIBITOR OF HCV

The present invention relates to synthesis procedures and intermediates of a compound offormula: (XVII) and the salts thereof.

Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350

SAR analysis performed with a limited set of cyclopentane-containing macrocycles led to the identification of N-[17-[2-(4-isopropylthiazole-2-yl)-7-methoxy-8-methylquinolin-4-yloxy]- 13-methyl-2,14-dioxo-3,13-diazatricyclo [13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamid e (TMC435350, 32c) as a potent inhibitor of HCV NS3/4A protease (Ki = 0.36 nM) and viral replication (replicon EC50 = 7.8 nM). TMC435350 also displayed low in vitro clearance and high permeability, which were confirmed by in vivo pharmacokinetic studies. TMC435350 is currently being evaluated in the clinics.