654655-69-3

Basic information

• Product Name: 3-benzyl-6-bromo-2-methoxyquinoline
• Synonyms: 3-benzyl-6-bromo-2-methoxyquinoline;6-Bromo-2-methoxy-3-benzylquinoline;6-bromo-2-methoxy-3-(phenylmethyl)-Quinoline;Bedaquiline int-2 3-Benzyl-6-bromo-2-methoxyquinoline;Quinoline, 6-bromo-2-methoxy-3-(phenylmethyl)-;Bedaquiline Impurity A;3-BENZYL 1-6-BROMO-2-METHOXYQUINOLINE
• CAS NO: 654655-69-3
• Molecular Formula: C₁₇H₁₄BrNO
• Molecular Weight: 328
• EINECS: 207-791-3
• Product Categories: bedaquiline intermediates
• Mol File: 654655-69-3.mol

Chemical Properties

• Melting Point: 82-83℃
• Boiling Point: --
• Flash Point: --
• Appearance: Off-White Solid
• Density: --
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.45±0.50(Predicted)
• CAS DataBase Reference: 3-benzyl-6-bromo-2-methoxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzyl-6-bromo-2-methoxyquinoline(654655-69-3)
• EPA Substance Registry System: 3-benzyl-6-bromo-2-methoxyquinoline(654655-69-3)

Safety Data

• Hazardous Substances Data: 654655-69-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Benzyl-6-bromo-2-methoxyquinoline is used as a reactant for the preparation of Bedaquiline (B119550), a potential drug in the treatment of tuberculosis. Its role in the synthesis of Bedaquiline highlights its importance in the development of novel therapeutic agents for combating drug-resistant tuberculosis.
As a chemical intermediate, 3-benzyl-6-bromo-2-methoxyquinoline may also have potential applications in the synthesis of other pharmaceutical compounds, given its unique structural features. However, further research and development are necessary to explore its full potential in various industries.

Upstream product

• 654655-68-2 3-benzyl-6-bromo-2-chloro-quinoline 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 106-40-1 4-bromo-aniline 
• 654655-80-8 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol 
• 316146-27-7 N-(4-bromophenyl)-3-phenylpropanamide 
• 100-39-0 benzyl bromide 
• 99455-05-7 2-methoxy-6-bromoquinoline 
• 501-52-0 3-Phenylpropionic acid 
• 645-45-4 hydrocinnamic acid chloride 
• 105479-98-9 ethyl 2-(acetoxy(phenyl)methyl)acrylate 
• 37442-45-8 ethyl 2-(hydroxy(phenyl)methyl)propenoate 
• 924658-20-8 2-[(4-bromo-phenylamino)-phenyl-methyl]-acrylic acid ethyl ester 
• 924633-09-0 3-benzyl-6-bromo-1H-quinolin-2-one 

Downstream Products

• 654655-75-1 2-(N-methylbenzyl)aminoethyl-1-naphthylketone 
• 1032357-22-4 C₃₆H₃₆BrClN₂O₂ 
• 1032357-22-4 C₃₆H₃₆BrClN₂O₂ 
• 1032444-47-5 C₄₂H₄₆BrN₃O₂ 
• 1032444-47-5 C₄₂H₄₆BrN₃O₂ 
• 1032444-51-1 C₄₄H₅₀BrN₃O₂ 
• 1032444-51-1 C₄₄H₅₀BrN₃O₂ 
• 1032444-61-3 C₄₄H₄₄BrN₃O₂ 
• 1032444-61-3 C₄₄H₄₄BrN₃O₂ 
• 1032444-66-8 C₄₅H₄₆BrN₃O₂ 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF BEDAQUILINE FUMARATE

The present disclosure relates to an improved process for the preparation of bedaquiline fumarate, comprising a step of preparing bedaquiline by reaction of 3-benzyl-6-bromo-2-methoxyquinoline 5 with 3-(dimethylamino)-l-(naphthalen-l-yl)propan-l-one 4 in the presence of lithium pyrrolidide.

New 1-(2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1-phenylbutan-2-ols with antituberculosis activity

New 4-dimethylamino-2-(naphthalen-1-yl)-1-phenyl-1-(quinolin-3-yl)butan-2-ols with antituberculosis activity were synthesized. (1R*,2S*)-1-(6-Bromo-2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1-phenylbutan-2-ol hydrocitrate exhibiting high

A method of high-efficiency production of beda quinoline

The invention relates to a method for high efficiency production of Bedaquiline. The method comprises that through optical resolution of 1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-2-butanol, Bedaquiline and other isomers are obtained, the other isomers undergo a reaction under the action of an alkali to produce key intermediate compounds A and B, and the key intermediate compounds A and B are separated and undergo a reaction to produce Bedaquiline. The method realizes high efficiency production of Bedaquiline, prevents large waste of materials, saves a cost and is suitable for large scale industrial production.

6-Cyano Analogues of Bedaquiline as Less Lipophilic and Potentially Safer Diarylquinolines for Tuberculosis

Bedaquiline (1) is a new drug for tuberculosis and the first of the diarylquinoline class. It demonstrates excellent efficacy against TB but induces phospholipidosis at high doses, has a long terminal elimination half-life (due to its high lipophilicity), and exhibits potent hERG channel inhibition, resulting in clinical QTc interval prolongation. A number of structural ring A analogues of bedaquiline have been prepared and evaluated for their anti-M.tb activity (MIC90), with a view to their possible application as less lipophilic second generation compounds. It was previously observed that a range of 6-substituted analogues of 1 demonstrated a positive correlation between potency (MIC90) toward M.tb and drug lipophilicity. Contrary to this trend, we discovered, by virtue of a clogP/M.tb score, that a 6-cyano (CN) substituent provides a substantial reduction in lipophilicity with only modest effects on MIC values, suggesting this substituent as a useful tool in the search for effective and safer analogues of 1.

Structural Simplification of Bedaquiline: the Discovery of 3-(4-(N,N-Dimethylaminomethyl)phenyl)quinoline-Derived Antitubercular Lead Compounds

Bedaquiline (BDQ) is a novel and highly potent last-line antituberculosis drug that was approved by the US FDA in 2013. Owing to its stereo-structural complexity, chemical synthesis and compound optimization are rather difficult and expensive. This study

A highly efficient way to recycle inactive stereoisomers of Bedaquiline into two previous intermediates via base-catalyzed Csp3Csp3 bond cleavage

Abstract Bedaquiline is a new medicine for pulmonary multi-drug resistant tuberculosis (MDR-TB), which is a pure enantiomer with two chiral centers. The current industrial preparation process requires the separation of active Bedaquiline from a mixture of four isomers. Obviously, direct dispose of the other three undesired stereoisomers will cause significant waste and increase the unnecessary cost of production. Here, we developed an efficient, facile and scalable process for recycling the inactive stereoisomers of Bedaquiline. All these inactive stereoisomers could be recycled by their conversion to two important intermediates in the Bedaquiline synthesis via a base-catalyzed Csp3Csp3 bond cleavage of a benzyl alcohol intermediate. And the precise conditions and mechanism of the base-catalyzed cleavage reaction were discussed.

QUINOLINE, NAPHTHALENE AND CONFORMATIONALLY CONSTRAINED QUINOLINE OR NAPHTHALENE DERIVATES AS ANTI-MYCOBACTERIAL AGENTS

The invention relates to a compound of general formula I, II, III, IV V VI, VII, VIII, IX, X or a tautomer and the stereochemically isomeric forms thereof or pharmaceutically acceptable salts thereof, a N-oxide form thereof or a pro-drug thereof. The compound is usable as a medicament for the treatment of mycobacterial disease

ANTIBACTERIAL QUINOLINE DERIVATIVES

The present invention relates to novel subst ituted quinoline derivatives according to the general Formula (Ia) or Formula (Ib): including any stereochemically isomeric form thereof, wherein 10 Q represents a radical of formula a N-oxide thereof, a pharmaceutically acceptable salt thereof or a solvate thereof. The claimed compounds are useful for the treatment of a bacterial infection. Also claimed is a composition comprising a pharmaceutically acceptable carrier and, as active ingredient, a therapeutically effective amount of the claimed compounds, the use of the claimed compounds or composit ions for the manufacture of a medicament for the treatment of a bacterial infection and a process for preparing the claimed compounds.

Trifluoroacetic acid: a more effective and efficient reagent for the synthesis of 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones and 3-arylmethyl-2-amino-quinolines from Baylis-Hillman derivatives via Claisen rearrangement

Trifluoroacetic acid has been discovered to be a highly effective and efficient reagent for the tandem Claisen rearrangement and cyclization reaction to yield 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones from compounds obtained from the SN2 r

QUINOLINE DERIVATIVES AS ANTIBACTERIAL AGENTS

Use of a compound for the manufacture of a medicament for the treatment of a bacterial infection provided that the bacterial infection is other than a Mycobacterial infection, said compound being a compound of formula (Ia) or (Ib) a pharmaceutically acceptable acid or base addition salt thereof, a stereochemically isomeric form thereof, a tautomeric form thereof or a N-oxide form thereof. Several of these compounds are also claimed as such. Further the combination of the above compounds with other antibacterial agents is described