1206524-81-3

Basic information

• Product Name: L-Proline, 3-Methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-L-valyl-4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-,Methyl ester,(4R)-
• Synonyms: L-Proline, 3-Methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-L-valyl-4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-,Methyl ester,(4R)-;(2S,4R)-methyl 4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)-1-((S)-3,3-dimethyl-2-((((1R,2R)-2-(pent-4-en-1-yl)cyclopropoxy)carbonyl)amino)butanoyl)pyrrolidine-2-carboxylate
• CAS NO: 1206524-81-3
• Molecular Formula: C₃₀H₃₉ClN₄O₇
• Molecular Weight: 603.10626
• Mol File: 1206524-81-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Proline, 3-Methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-L-valyl-4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-,Methyl ester,(4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 3-Methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-L-valyl-4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-,Methyl ester,(4R)-(1206524-81-3)
• EPA Substance Registry System: L-Proline, 3-Methyl-N-[[[(1R,2R)-2-(4-penten-1-yl)cyclopropyl]oxy]carbonyl]-L-valyl-4-[(3-chloro-7-Methoxy-2-quinoxalinyl)oxy]-,Methyl ester,(4R)-(1206524-81-3)

Safety Data

• Hazardous Substances Data: 1206524-81-3(Hazardous Substances Data)

Upstream product

• 31910-18-6 2,3-dihydroxy-6-methoxyquinoxaline 
• 1425038-19-2 (S)-3,3-dimethyl-2-(((1R,2R)-2-(pent-4-ynyl)cyclopropoxy)carbonylamino)butanoic acid 
• 1425038-20-5 (2S,4R)-4-[(3-chloro-7-methoxyquinoxalin-2-yl)oxy]-2-(methoxycarbonyl)pyrrolidin-1-ium methanesulfonate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 39267-04-4 2,3-dichloro-6-methoxyquinoxaline 
• 1026200-27-0 3-methyl-N-({[(1R,2R)-2-pent-4-en-1-ylcyclopropyl]oxy}carbonyl)-L-valine 
• 124471-62-1 (E)-(hepta-1,6-dien-1-yloxy)trimethylsilane 
• 144164-32-9 methyl 3-methyl-N-(oxomethylene)-L-valinate 
• 63038-27-7 L-tert-leucine methyl ester hydrochloride 
• 59548-39-9 4-methoxyphenylene-1,2-diamine dihydrochloride 
• 1026200-25-8 methyl 3-methyl-N-({[(1R,2R)-2-pent-4-en-1-ylcyclopropyl]oxy}carbonyl)-L-valinate 
• 1384277-05-7 trans 2-(pent-4-en-1-yl)cyclopropanol 
• 1206524-79-9 1-(tert-butyl) 2-methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate 
• 1361028-94-5 methyl (4R)-4-[(3-chloro-7-methoxyquinoxalin-2-yl)oxy]-L-prolinate hydrochloride 

Downstream Products

• 1350514-68-9 grazoprevir 
• 1206524-84-6 methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxa-diazacyclononadecino[11,12-b]quinoxaline-8-carboxylate 
• 1206524-85-7 (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradeca-hydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylic acid hydrate 
• 1206524-83-5 methyl (1aR,5S,8S,10R,18E,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,20,21,22,22a-dodecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylate 

Relevant articles and documents

Synthesis of Grazoprevir, a Potent NS3/4a Protease Inhibitor for the Treatment of Hepatitis C Virus

An efficient synthesis of grazoprevir is reported. Starting from four readily available building blocks, grazoprevir is prepared in 51% overall yield and >99.9% purity for pharmaceutical use.

METHODS AND INTERMEDIATES FOR THE PREPARATION OF MACROLACTAMS

The present invention relates to synthetic processes useful in the preparation of macrolactams that inhibit hepatitis C virus (HCV), specifically macrolactam compounds that inhibit the HCV NS3 protease activity and have application in the treatment of conditions caused by HCV. The present invention also encompasses intermediates useful in the disclosed synthetic processes and the methods of their preparation.

Discovery of MK-5172, a macrocyclic hepatitis C virus NS3/4a protease inhibitor

A new class of HCV NS3/4a protease inhibitors containing a P2 to P4 macrocyclic constraint was designed using a molecular modeling-derived strategy. Building on the profile of previous clinical compounds and exploring the P2 and linker regions of the series allowed for optimization of broad genotype and mutant enzyme potency, cellular activity, and rat liver exposure following oral dosing. These studies led to the identification of clinical candidate 15 (MK-5172), which is active against genotype 1-3 NS3/4a and clinically relevant mutant enzymes and has good plasma exposure and excellent liver exposure in multiple species.

Macrocyclic Quinoxaline Compounds as HCV NS3 Protease Inhibitors

The present invention relates to macrocyclic a compound of formula (I) and its use as inhibitors of the hepatitis C virus (HCV) NS3 protease, and in treating or preventing HCV infections.