654653-93-7

Basic information

• Product Name: (αR,βS)-rel-Bedaquiline
• Synonyms: (αR,βS)-rel-Bedaquiline;(1R,2S)-rac-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(methylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
• CAS NO: 654653-93-7
• Molecular Formula: C32H31BrN2O2
• Molecular Weight: 555.50474
• Product Categories: Aromatics, Heterocycles, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 654653-93-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 702.7°Cat760mmHg
• Flash Point: 378.8°C
• Appearance: /
• Density: 1.322g/cm³
• Vapor Pressure: 1.01E-20mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 13.05±0.29(Predicted)
• CAS DataBase Reference: (αR,βS)-rel-Bedaquiline(CAS DataBase Reference)
• NIST Chemistry Reference: (αR,βS)-rel-Bedaquiline(654653-93-7)
• EPA Substance Registry System: (αR,βS)-rel-Bedaquiline(654653-93-7)

Safety Data

• Hazardous Substances Data: 654653-93-7(Hazardous Substances Data)

Usage

Description

(αR,βS)-rel-Bedaquiline, a diarylquinoline derivative, is a novel compound currently in clinical development for the treatment of tuberculosis. It is characterized by its off-white solid appearance and has demonstrated high activity against both drug-susceptible and multidrug-resistant strains of Mycobacterium tuberculosis. (αR,βS)-rel-Bedaquiline works by inhibiting mycobacterial ATP synthase, which is essential for the survival and replication of the bacteria.

Uses

Used in Pharmaceutical Industry:
(αR,βS)-rel-Bedaquiline is used as an antitubercular agent for the treatment of tuberculosis. It is particularly effective against both drug-susceptible and multidrug-resistant strains of Mycobacterium tuberculosis due to its ability to inhibit mycobacterial ATP synthase, a crucial enzyme for bacterial survival and replication.
Used in Clinical Development:
(αR,βS)-rel-Bedaquiline is used as a promising candidate in clinical development for the treatment of tuberculosis. Its unique mechanism of action and high activity against various strains of Mycobacterium tuberculosis make it a valuable addition to the current arsenal of antitubercular drugs, potentially offering new treatment options for patients suffering from drug-resistant forms of the disease.

InChI:InChI=1/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3/h4-17,20-21,30,36H,18-19H2,1-3H3/t30-,32-/m1/s1

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 
• 1298044-25-3 (2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanone 
• 1298044-27-5 (1R)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylpent-4-en-2-ol 
• 1298044-29-7 C₃₀H₂₄BrNO₃ 
• 1298044-31-1 (4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-(naphthalen-1-yl)-4-phenylbutane-1,3-diol 
• 1298044-33-3 (4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl methanesulfonate 
• 124-40-3 dimethyl amine 
• 1298044-13-9 ethyl (E)-3-(6-bromo-2-chloroquinolin-3-yl)acrylate 

Downstream Products

• 1032265-50-1 C₃₉H₃₅BrN₂O₃ 

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 racemate and intermediates thereof

The invention belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of a bedaquiline racemate and intermediates thereof. According to the method disclosed by the invention, convenient, efficient and economical synthesis and industrial production of the bedaquiline and the intermediates thereof are realized. Specifically, the method provided by the invention has the following advantages that: the ultralow-temperature reaction required for preparing bedaquiline from a compound I and a compound II is thoroughly changed, and the original ultralow-temperature reaction which is difficult to realize industrially is changed into the reaction at a conventional temperature, so that large-scale industrial production becomes possible; according to the method disclosed by the invention, the conversion rate of the reaction substrate is greatly improved, the reaction yield is improved, the product is easier to crystallize and purify (recrystallizationof the intermediates can be realized by using a conventional solvent ethyl acetate or methanol), and meanwhile, the production cost is reduced.

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.