654655-80-8

Basic information

• Product Name: Bedaquiline (Mixture of DiastereoMers)
• Synonyms: Bedaquiline (Mixture of DiastereoMers)
• CAS NO: 654655-80-8
• Molecular Formula: C₃₂H₃₁BrN₂O₂
• Molecular Weight: 555.50474
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 654655-80-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 702.7±60.0 °C(Predicted)
• Appearance: /
• Density: 1.322±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Acetonitrile (Slightly, Heated) Chloroform (Slightly, Heated), DMSO (Slightly)
• PKA: 13.05±0.29(Predicted)
• CAS DataBase Reference: Bedaquiline (Mixture of DiastereoMers)(CAS DataBase Reference)
• NIST Chemistry Reference: Bedaquiline (Mixture of DiastereoMers)(654655-80-8)
• EPA Substance Registry System: Bedaquiline (Mixture of DiastereoMers)(654655-80-8)

Safety Data

• Hazardous Substances Data: 654655-80-8(Hazardous Substances Data)

Usage

Description

Bedaquiline (Mixture of DiastereoMers) is a diarylquinoline derivative with potent mycobacterial inhibitory properties, making it a significant pharmaceutical compound in the fight against tuberculosis.

Uses

Used in Pharmaceutical Industry:
Bedaquiline (Mixture of DiastereoMers) is used as an antituberculosis agent for its ability to inhibit mycobacterial growth, offering a new treatment option for drug-resistant tuberculosis cases and improving patient outcomes.

Upstream product

• 10320-49-7 3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone 
• 654655-69-3 3-benzyl-6-bromo-2-methoxyquinoline 
• 941-98-0 1'-naphthacetophenone 
• 654653-93-7 rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol 
• 106-40-1 4-bromo-aniline 
• 316146-27-7 N-(4-bromophenyl)-3-phenylpropanamide 
• 654655-68-2 3-benzyl-6-bromo-2-chloro-quinoline 
• 66-77-3 1-naphthaldehyde 
• 1189178-87-7 6-bromo-3-[chloro(phenyl)methyl]-2-methoxyquinoline 
• 924632-90-6 (±)-3-bromo-3-(bromo(phenyl)methyl)-2-methoxyquinoline 
• 2631-61-0 3-dimethylamino-1-(naphthalen-2-yl)propan-1-one hydrochloride 

Downstream Products

• 1032468-55-5 C₃₂H₂₉BrN₂O 
• 916800-77-6 C₃₃H₃₂N₂O₃ 
• 654655-69-3 3-benzyl-6-bromo-2-methoxyquinoline 
• 10320-49-7 3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone 
• 843663-66-1 bedaquiline 
• 2752-87-6 3-(dimethylamino)-1-(naphthalen-2-yl)propan-1-one 
• 845533-86-0 [4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate 

Relevant articles and documents

PROCESS FOR PREPARING (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol AND PHARMACEUTICALLY ACCEPTABLE SALT

The present invention relates to a process for the preparation of bedaquiline ((1R, 2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol) or a pharmaceutically acceptable salt thereof, the process comprising: isolating (1R, 2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol. The method can achieve large-scale preparation, so that the preparation method is an economical preparation method and has high yield.

Preparation method of bedaquiline and intermediate thereof

The invention discloses a preparation method of a bedaquiline racemate and a key intermediate compound used in the preparation method. According to the method for preparing the bedaquiline racemate, the ultra-low temperature reaction in the prior art is changed, and the ultra-low temperature reaction which is difficult to realize in the prior art is carried out at the conventional temperature, sothat large-scale industrialization becomes possible. Besides, the method provided by the invention greatly improves the conversion rate of the reaction substrate, improves the reaction yield, makes the product more easily crystallized and purified, and reduces the production cost at the same time.

For preparing beda quinoline intermediate and its preparation method and application

The invention discloses an intermediate for preparing bedaquiline and a preparation method therefor. The intermediate disclosed by the invention has the advantages that the intermediate avoids hydrogenation and enolization of an alpha-site in the intermediate, reduces occurrence of side reactions, and increases the conversion rate of raw materials and the total yield of reaction, and is suitable for large-scale industrial production. The intermediate for preparing bedaquiline is characterized by being a compound with a structural formula (9) or an optical isomer thereof: FORMULA is shown in the description.