24188-74-7

Basic information

• Product Name: 7-CHLORO-1-HYDROXYISOQUINOLINE
• Synonyms: 7-CHLORO-1-HYDROXYISOQUINOLINE;7-CHLORO-1(2H)-ISOQUINOLONE;7-Chloroisoquinolin-1-ol;7-Chloro-1(2H)-isoquinolinone;7-chloro-2H-isoquinolin-1-one
• CAS NO: 24188-74-7
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.6
• Mol File: 24188-74-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 245-247 °C(Solv: methanol (67-56-1))
• Boiling Point: 414.876°C at 760 mmHg
• Flash Point: 204.71°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.99±0.20(Predicted)
• CAS DataBase Reference: 7-CHLORO-1-HYDROXYISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-1-HYDROXYISOQUINOLINE(24188-74-7)
• EPA Substance Registry System: 7-CHLORO-1-HYDROXYISOQUINOLINE(24188-74-7)

Safety Data

• Hazardous Substances Data: 24188-74-7(Hazardous Substances Data)

Usage

Description

7-CHLORO-1-HYDROXYISOQUINOLINE is an organic compound with the molecular formula C9H7ClNO. It is a derivative of isoquinoline, which is a tricyclic aromatic alkaloid. 7-CHLORO-1-HYDROXYISOQUINOLINE is characterized by the presence of a chlorine atom at the 7th position and a hydroxyl group at the 1st position. It is known for its potential applications in the pharmaceutical and chemical industries due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
7-CHLORO-1-HYDROXYISOQUINOLINE is used as a reagent for the preparation of various compounds, including methoxyisoquinoline derivatives. It plays a crucial role in the synthesis of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor, which is utilized for the treatment of hepatitis C virus infection. This application highlights the compound's importance in the development of antiviral medications.
Used in Medicinal Chemistry Research:
7-CHLORO-1-HYDROXYISOQUINOLINE is employed as a key intermediate in the synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists. These antagonists are significant in the field of medicinal chemistry, as they have the potential to be developed into new drugs for the treatment of various disorders related to the serotonin system, such as anxiety, depression, and gastrointestinal disorders.

InChI:InChI=1/C9H6ClNO/c10-7-2-1-6-3-4-11-9(12)8(6)5-7/h1-5H,(H,11,12)

Upstream product

• 1028252-12-1 C₁₁H₁₃ClN₂O 
• 1615-02-7 p-chlorocinnamic acid 
• 1028252-11-0 5-chloro-2-methylbenzamide 
• 7499-06-1 5-chloro-2-methylbenzoic acid 
• 21900-40-3 5-chloro-2-methylbenzoyl chloride 
• 70810-26-3 7-chloroisoquinoline 2-oxide 
• 131002-05-6 5-chloro-2-ethenylbenzamide 
• 130874-98-5 5-chloro-2-<(E)-2-(dimethylamino)vinyl>benzonitrile 
• 83421-78-7 (E)-3-(4-Chloro-phenyl)-acryloyl azide 
• 50712-70-4 5-chloro-2-methylbenzonitrile 
• 131002-02-3 2-bromo-5-chlorobenzamide 
• 21663-61-6 2,5-dichlorobenzonitrile 

Downstream Products

• 444898-44-6 C₃₅H₂₆ClNO₈ 
• 104604-82-2 10-chloro-4-oxo-3-phenyl-4H-benzoquinolizine-1-carboxylic acid 
• 104587-27-1 methyl 10-chloro-4-oxo-3-phenyl-4H-benzoquinolizine-1-carboxylate 
• 104587-01-1 10-chloro-1-<(3-methoxyazetidin-1-yl)carbonyl>3-phenyl-4H-benzoquinolizin-4-one 
• 104604-65-1 10-chloro-1-<<(S)-2-(methoxymethyl)pyrrolidin-1-yl>carbonyl>-3-phenyl-4H-benzoquinolizin-4-one 
• 104604-67-3 10-chloro-1-<<(R)-2-(methoxymethyl)pyrrolidin-1-yl>carbonyl>-3-phenyl-4H-benzoquinolizin-4-one 
• 630423-35-7 7-chloro-4-methoxy-2H-isoquinolin-1-one 
• 630423-36-8 1,7-dichloro-4-methoxyisoquinoline 
• 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 
• 953421-74-4 4-bromo-1,7-dichloroisoquinoline 
• 1028252-15-4 (2S,4R)-1-(tert-butoxycarbonyl)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)pyrrolidine-2-carboxylic acid 
• 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 
• 70810-24-1 1,7-dichloroisoquinoline 

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).

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

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.