630423-36-8

Basic information

• Product Name: Isoquinoline, 1,7-dichloro-4-Methoxy-
• Synonyms: Isoquinoline, 1,7-dichloro-4-Methoxy-;1,7-dichloro-4-Methoxyisoquinoline;Asunaprevir Intermediate 2;Asunaprevir N-1
• CAS NO: 630423-36-8
• Molecular Formula: C₁₀H₇Cl₂NO
• Molecular Weight: 228.07468
• Mol File: 630423-36-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 137.0 to 142.0 °C
• Boiling Point: 355.7±37.0 °C(Predicted)
• Appearance: /
• Density: 1.384±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.98±0.34(Predicted)
• CAS DataBase Reference: Isoquinoline, 1,7-dichloro-4-Methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 1,7-dichloro-4-Methoxy-(630423-36-8)
• EPA Substance Registry System: Isoquinoline, 1,7-dichloro-4-Methoxy-(630423-36-8)

Safety Data

• Hazardous Substances Data: 630423-36-8(Hazardous Substances Data)

Usage

Uses

1,7-Dichloro-4-methoxyisoquinoline acts as a reagent in the synthesis and biological evaluations of P4-benzoxaborole-substituted macrocyclic inhibitors of HCV NS3 protease. Preparation, SAR of methoxyisoquinoline derivatives and discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection.

Upstream product

• 21900-40-3 5-chloro-2-methylbenzoyl chloride 
• 7499-06-1 5-chloro-2-methylbenzoic acid 
• 1028252-11-0 5-chloro-2-methylbenzamide 
• 1028252-14-3 1,7-dichloroisoquinolin-4-ol 
• 74-88-4 methyl iodide 
• 1028252-13-2 4-bromo-7-chloroisoquinolin-1-ol 
• 24188-74-7 7-chloroisoquinolin-1-ol 
• 1615-02-7 p-chlorocinnamic acid 
• 1028252-13-2 4-bromo-7-chloro-2H-isoquinolin-1-one 
• 67-56-1 methanol 
• 953421-74-4 4-bromo-1,7-dichloroisoquinoline 
• 24188-74-7 7-chloroisoquinoline-1(2Η)-one 
• 26386-88-9 diphenyl phosphoryl azide 
• 630423-35-7 7-chloro-4-methoxy-2H-isoquinolin-1-one 

Downstream Products

• 630420-16-5 tert-butyl ((S)-1-((2S,4R)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)-2-(((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate 
• 1169846-35-8 (2S,4R)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)-N-((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)pyrrolidine-2-carboxamide hydrochloride 
• 1028252-15-4 (2S,4R)-1-(tert-butoxycarbonyl)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)pyrrolidine-2-carboxylic acid 

Relevant articles and documents

The discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection

The discovery of asunaprevir (BMS-650032, 24) is described. This tripeptidic acylsulfonamide inhibitor of the NS3/4A enzyme is currently in phase III clinical trials for the treatment of hepatitis C virus infection. The discovery of 24 was enabled by employing an isolated rabbit heart model to screen for the cardiovascular (CV) liabilities (changes to HR and SNRT) that were responsible for the discontinuation of an earlier lead from this chemical series, BMS-605339 (1), from clinical trials. The structure-activity relationships (SARs) developed with respect to CV effects established that small structural changes to the P2* subsite of the molecule had a significant impact on the CV profile of a given compound. The antiviral activity, preclincial PK profile, and toxicology studies in rat and dog supported clinical development of BMS-650032 (24).

Process for Synthesizing Substituted Isoquinolines

The present disclosure generally relates to a process for synthesizing optionally substituted 1-chloro-4-methoxyisoquinolines. The present disclosure also relates to intermediates useful in this process.

Hepatitis C Virus Inhibitors

Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.