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6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol
Cas No: 843663-66-1
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
843663-66-1 6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol
Cas No: 843663-66-1
USD $ 40.0-50.0 / Gram 1 Gram 1000 Metric Ton/Day WUHAN MULEI NEW MATERIAL CO., LTD Contact Supplier
Bedaquiline manufacturer/supplier
Cas No: 843663-66-1
No Data 1 Gram 1000 Metric Ton/Month Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd Contact Supplier
Bedaquiline
Cas No: 843663-66-1
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bedaquinline
Cas No: 843663-66-1
USD $ 10.0-10.0 / Gram 1 Gram 50 Kilogram/Month Enke Pharma-tech Co.,Ltd. (Cangzhou, China ) Contact Supplier
(αS,βR)-Bedaquiline
Cas No: 843663-66-1
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
TIANFU-CHEM - TMC-207
Cas No: 843663-66-1
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Pharmaceutical Grade CAS 843663-66-1 with competitive price
Cas No: 843663-66-1
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High purity Bedaquiline CAS No.:843663-66-1
Cas No: 843663-66-1
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bedaquinline 99%
Cas No: 843663-66-1
USD $ 86.0-100.0 / Kilogram 1 Kilogram 100 Kilogram/Month Baoji Guokang Healthchem co.,ltd Contact Supplier

843663-66-1 Usage

Pharmacological Function

Bedaquinoline has the same bactericidal activity against both sensitive and resistant strains of mycobacterium tuberculosis as well as on dormant bacteria.

Synthetic Methods

Synthetic route of Bedaquiline
Fig: Synthetic route of Bedaquiline

Uses

Labeled Bedaquiline, intended for use as an internal standard for the quantification of Bedaquiline by GC- or LC-mass spectrometry.

Pharmacokinetics

Bedaquinoline is easy for oral assimilation. The bioavailability of Bedaquinoline taken with food is twice higher than when taken with an empty stomach. It reaches its blood concentration in 5 hours after taken and has a plasma protein binding rate of 99.9% as well as a plasma half-life of 173 hours. Bedaquinoline can be widely distributed in human body with a homeostasis distribution volume of 1000L. Its clearance rate is low enough and the elimination half-life is 5.5 months. Bedaquinoline is metabolize into metabolite 1~8 in the demethylation mainly through CYP3A4 and partly though CYP2C8 and CYP2C19. Metabolite 2 (M2), the most important metabolite,  which has only 1/3-1/6 the activity of Bedaquinoline, yet present a more strong cytotoxicity and is more likely to cause the drug-induced phospholipidosis. Bedaquinoline and its metabolites are mostly excreted by feces, only 1% to 4% by urine.

Pharmacology

The proton pump on the cell’s ATP synthetase, which is a crucial enzyme for M. tuberculosis (TB) to synthesize ATP, is the unique and specific locus of Bedaquinoline.
After the combination onto the oligomer and lipoprotein subunit c, Bedaquinoline can inhibit the synthesis of ATP and bring the death to the bacterium cell. Compared with those existing anti-TB medicines, it presents a novel pharmacology and no cross resistance effect was found between Bedaquinoline and other anti-TB medicines. The gene sequence of the subunit c of ATP synthetase is named as atpE, whose amino acid sequence is highly conservative. The resistance of TB to Bedaquinoline comes from its reduced combination onto subunit c of ATP synthetase due to the mutation of the 63rd or 66th on atpE.

Overview

Bedaquiline, formally called (1R, 2S)-1-(6-Bromo-2-methoxy-3-quinolinyl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenyl-2-butanol in chemistry and known as Sirturo in commercial, is a new anti-mycobacterial medicine of diarylquinolines. It impinges on the
ATP synthesis of Mycobacterium tuberculosis by inhibiting the activity of proton pump on the cell’s ATP synthetase, and thereby eliminates M. tuberculosis (TB). It’s used for adult multi-drug resistant tuberculosis (MDR-PTB).

Adverse Effect

Common adverse reactions are nausea, headache, arthralgia, loss of appetite, vomiting and rash, dizziness, elevated transaminase, increased hemodiastase, muscle pain, diarrhea and prolonged TQ interval.

Taboo

1.The allergic to this product;
2.Patients suffer serious dysfunction of heart, liver, kidney (relative contraindication);
3.Pregnant women, lactating women, children, the old and co-infected HIV sufferers (relative contraindication).

Uses

(αS,βR)-Bedaquiline is a diarylquinoline derivative that acts as a mycobacterial inhibitor. Bedaquiline shows promise as potential drug in the treatment of tuberculosis.

843663-66-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name TMC-207

1.2 Other means of identification

Product number -
Other names methyl 6-azanyl-2-benzamido-hexanoate hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:843663-66-1 SDS

843663-66-1Synthetic route

(3S,4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl-4-methylbenzenesulfonate
1229443-16-6

(3S,4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl-4-methylbenzenesulfonate

dimethyl amine
124-40-3

dimethyl amine

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 40℃; for 10h; Inert atmosphere;62%
rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol

rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol

6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol*(11bR)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide

6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol*(11bR)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
Stage #1: rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol; 6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol*(11bR)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide With (R)-1,1'-binaphthyl-2,2'-phosphoric acid In dimethyl sulfoxide; acetone at 20 - 50℃; for 3.16667 - 5.75h; Heating / reflux; Resolution of racemate;
Stage #2: In acetone at 20 - 30℃; for 2.75 - 4h; Heating / reflux;
Stage #3: With potassium carbonate In water; toluene at 80 - 85℃; for 0.0833333 - 0.25h; Purification / work up;
39%
1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
With (R)-1,1'-binaphthyl-2,2'-phosphoric acid In dimethyl sulfoxide; acetone at 20℃; for 3h; Reflux;39%
Stage #1: 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol With (R)-1,1'-binaphthyl-2,2'-phosphoric acid In dimethyl sulfoxide; acetone at 20℃; for 2h; Resolution of racemate; Reflux;
Stage #2: With potassium carbonate In toluene Resolution of racemate; Reflux;
39%
3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
10320-49-7

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

C

(R,S)-bedaquiline

(R,S)-bedaquiline

Conditions
ConditionsYield
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -20℃; for 0.25h; Nitrogen atmosphere;
Stage #2: 3-benzyl-6-bromo-2-methoxyquinoline In tetrahydrofuran at -70℃; for 0.5h;
Stage #3: 3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone With water more than 3 stages;
(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanone
1298044-25-3

(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanone

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
1.2: 0.5 h
2.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
3.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
5.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(1R)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylpent-4-en-2-ol
1298044-27-5

(1R)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylpent-4-en-2-ol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
2: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
3: triethylamine / dichloromethane / 3 h / 0 - 20 °C
4: tetrahydrofuran / 24 h / 45 °C
View Scheme
C30H24BrNO3
1298044-29-7

C30H24BrNO3

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C
3: tetrahydrofuran / 24 h / 45 °C
View Scheme
(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-(naphthalen-1-yl)-4-phenylbutane-1,3-diol
1298044-31-1

(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-(naphthalen-1-yl)-4-phenylbutane-1,3-diol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
2: tetrahydrofuran / 24 h / 45 °C
View Scheme
(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl methanesulfonate
1298044-33-3

(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl methanesulfonate

dimethyl amine
124-40-3

dimethyl amine

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
In tetrahydrofuran at 45℃; for 24h;
ethyl (E)-3-(6-bromo-2-chloroquinolin-3-yl)acrylate
1298044-13-9

ethyl (E)-3-(6-bromo-2-chloroquinolin-3-yl)acrylate

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 - 20 °C
1.2: 4 h
2.1: methanol / 8 h / 80 °C
3.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.67 h / -20 °C / Molecular sieve
3.2: 4 h / -20 °C
4.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
4.2: 3 h / -40 °C
4.3: 3 h
5.1: / dichloromethane / 1 h / 0 - 20 °C
6.1: diethyl ether / 1 h / 0 °C
7.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
8.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
8.2: 0.5 h
9.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
10.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
11.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
12.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(E)-3-(6-bromo-2-chloroquinolin-3-yl)prop-2-en-1-ol
1298044-15-1

(E)-3-(6-bromo-2-chloroquinolin-3-yl)prop-2-en-1-ol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: methanol / 8 h / 80 °C
2.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.67 h / -20 °C / Molecular sieve
2.2: 4 h / -20 °C
3.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
3.2: 3 h / -40 °C
3.3: 3 h
4.1: / dichloromethane / 1 h / 0 - 20 °C
5.1: diethyl ether / 1 h / 0 °C
6.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
7.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
7.2: 0.5 h
8.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
9.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
10.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
11.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(E)-3-(6-bromo-2-methoxyquinolin-3-yl)prop-2-en-1-ol
1298044-17-3

(E)-3-(6-bromo-2-methoxyquinolin-3-yl)prop-2-en-1-ol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.67 h / -20 °C / Molecular sieve
1.2: 4 h / -20 °C
2.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
2.2: 3 h / -40 °C
2.3: 3 h
3.1: / dichloromethane / 1 h / 0 - 20 °C
4.1: diethyl ether / 1 h / 0 °C
5.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
6.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
6.2: 0.5 h
7.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
8.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
9.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
10.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
[(2S,3S)-3-(6-bromo-2-methoxyquinolin-3-yl)oxiran-2-yl]methanol
1298044-10-6

[(2S,3S)-3-(6-bromo-2-methoxyquinolin-3-yl)oxiran-2-yl]methanol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
1.2: 3 h / -40 °C
1.3: 3 h
2.1: / dichloromethane / 1 h / 0 - 20 °C
3.1: diethyl ether / 1 h / 0 °C
4.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
5.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
5.2: 0.5 h
6.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
7.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
8.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
9.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(2R,3R)-3-(6-bromo-2-methoxyquinolin-3-yl)-3-phenylpropane-1,2-diol
1298044-19-5

(2R,3R)-3-(6-bromo-2-methoxyquinolin-3-yl)-3-phenylpropane-1,2-diol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: / dichloromethane / 1 h / 0 - 20 °C
2.1: diethyl ether / 1 h / 0 °C
3.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
4.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
4.2: 0.5 h
5.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
6.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
7.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
8.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
C18H14BrNO2
1298044-21-9

C18H14BrNO2

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: diethyl ether / 1 h / 0 °C
2.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
3.2: 0.5 h
4.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
5.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
6.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
7.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanol
1298044-24-2

(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
2.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
2.2: 0.5 h
3.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
4.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
5.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
6.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
6-bromo-2-chloro-3-formylquinoline
73568-35-1

6-bromo-2-chloro-3-formylquinoline

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C
1.2: 2 h
2.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 - 20 °C
2.2: 4 h
3.1: methanol / 8 h / 80 °C
4.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.67 h / -20 °C / Molecular sieve
4.2: 4 h / -20 °C
5.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
5.2: 3 h / -40 °C
5.3: 3 h
6.1: / dichloromethane / 1 h / 0 - 20 °C
7.1: diethyl ether / 1 h / 0 °C
8.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
9.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
9.2: 0.5 h
10.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
11.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
12.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
13.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
3-benzyl-6-bromo-2-methoxyquinoline
654655-69-3

3-benzyl-6-bromo-2-methoxyquinoline

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
10320-49-7

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
1.2: 12 h / -78 - -40 °C
2.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
2.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
1'-naphthacetophenone
941-98-0

1'-naphthacetophenone

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / ethanol / 12 h / Reflux; Inert atmosphere
2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 12 h / -78 - -40 °C
3.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
3.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol

rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Stage #1: rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol With (R)-1,1'-binaphthyl-2,2'-phosphoric acid In dimethyl sulfoxide; acetone at 20℃; for 2h; Reflux; Inert atmosphere;
Stage #2: With potassium carbonate In water; toluene at 80℃; for 0.5h; Inert atmosphere;
A 0.35 g
B n/a
4-bromo-aniline
106-40-1

4-bromo-aniline

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine / 0 - 20 °C / Inert atmosphere
2.1: trichlorophosphate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
3.1: methanol / Reflux; Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: 12 h / -78 - -40 °C
5.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
5.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
N-(4-bromophenyl)-3-phenylpropanamide
316146-27-7

N-(4-bromophenyl)-3-phenylpropanamide

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: trichlorophosphate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
2.1: methanol / Reflux; Inert atmosphere
3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
3.2: 12 h / -78 - -40 °C
4.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
4.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
3-benzyl-6-bromo-2-chloro-quinoline
654655-68-2

3-benzyl-6-bromo-2-chloro-quinoline

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanol / Reflux; Inert atmosphere
2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 12 h / -78 - -40 °C
3.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
3.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
3-benzyl-6-bromo-2-methoxyquinoline
654655-69-3

3-benzyl-6-bromo-2-methoxyquinoline

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
10320-49-7

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone

A

bedaquiline
843663-66-1

bedaquiline

B

(R,S)-bedaquiline

(R,S)-bedaquiline

C

C32H31BrN2O2

C32H31BrN2O2

Conditions
ConditionsYield
With n-butyllithium; (S)-N-benzylprolinol; lithium diisopropyl amide In tetrahydrofuran; hexane; n-heptane; ethylbenzene at -78 - -72℃; for 3h; Reagent/catalyst; Inert atmosphere;A n/a
B n/a
C n/a
3-dimethylamino-1-(naphthalene-1-yl)-prop-2-en-1-one

3-dimethylamino-1-(naphthalene-1-yl)-prop-2-en-1-one

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 1 h / -20 °C
1.2: 12 h
2.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 12 h / 20 °C
3.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 3 h / 20 °C / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 1 h / -20 °C
1.2: 12 h
2.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 12 h / 20 °C
3.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Resolution of racemate; Reflux
3.2: Resolution of racemate; Reflux
View Scheme
1'-naphthacetophenone
941-98-0

1'-naphthacetophenone

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 24 h / 120 °C
2.1: lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 1 h / -20 °C
2.2: 12 h
3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 12 h / 20 °C
4.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 3 h / 20 °C / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 24 h / 100 °C
2.1: lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 1 h / -20 °C
2.2: 12 h
3.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 12 h / 20 °C
4.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Resolution of racemate; Reflux
4.2: Resolution of racemate; Reflux
View Scheme
3-benzyl-6-bromo-2-methoxyquinoline
654655-69-3

3-benzyl-6-bromo-2-methoxyquinoline

3-(dimethylamino)-1-(naphthalen-2-yl)propan-1-one
2752-87-6

3-(dimethylamino)-1-(naphthalen-2-yl)propan-1-one

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
With acetic acid; lithium diisopropyl amide In tetrahydrofuran at -80 - -70℃; Inert atmosphere;9.45 g
3-benzyl-6-bromo-2-methoxyquinoline
654655-69-3

3-benzyl-6-bromo-2-methoxyquinoline

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
10320-49-7

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone

A

bedaquiline
843663-66-1

bedaquiline

B

(R,S)-bedaquiline

(R,S)-bedaquiline

Conditions
ConditionsYield
Stage #1: 3-benzyl-6-bromo-2-methoxyquinoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: 3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #3: With acetic acid In tetrahydrofuran at 0℃; Overall yield = 84.4 percent;
hydrocinnamic acid chloride
645-45-4

hydrocinnamic acid chloride

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 5 - 10 °C
2.1: trichlorophosphate / acetonitrile / 3 h / 75 - 80 °C
3.1: 12 h / 60 - 65 °C
4.1: lithium diisopropyl amide / tetrahydrofuran / -75 - -70 °C
4.2: 2.5 h / -75 - -70 °C
View Scheme
bedaquiline
843663-66-1

bedaquiline

citric acid
77-92-9

citric acid

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol citrate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol citrate

Conditions
ConditionsYield
In isopropyl alcohol at 50 - 80℃; for 1h;96.6%
bedaquiline
843663-66-1

bedaquiline

(1R,2S)-4-(dimethylamino)-1-(2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

(1R,2S)-4-(dimethylamino)-1-(2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; triethylamine In tetrahydrofuran at 30℃; under 760.051 Torr; for 4h; Solvent; Temperature;90%
bedaquiline
843663-66-1

bedaquiline

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate
845533-86-0

[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate

Conditions
ConditionsYield
In isopropyl alcohol at 20 - 70℃; for 18h; Heating / reflux;82%
In isopropyl alcohol at 70 - 80℃; for 1h;
In isopropyl alcohol at 75 - 80℃;15 g
In propan-1-ol; acetone
bedaquiline
843663-66-1

bedaquiline

m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

C39H37BrN2O3
1032266-07-1

C39H37BrN2O3

Conditions
ConditionsYield
Stage #1: bedaquiline With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1h;
Stage #2: m-bromobenzoic aldehyde In tetrahydrofuran; hexane at -70℃; for 1h;
Stage #3: With water In tetrahydrofuran; hexanes at -40℃;
37%
bedaquiline
843663-66-1

bedaquiline

citric acid
77-92-9

citric acid

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol citrate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol citrate

Conditions
ConditionsYield
In isopropyl alcohol37%
bedaquiline
843663-66-1

bedaquiline

tartaric acid
87-69-4

tartaric acid

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol tartrate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol tartrate

Conditions
ConditionsYield
In acetonitrile34%
bedaquiline
843663-66-1

bedaquiline

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol sulphate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol sulphate

Conditions
ConditionsYield
With sulfuric acid In isopropyl alcohol33%
bedaquiline
843663-66-1

bedaquiline

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol phosphate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol phosphate

Conditions
ConditionsYield
With phosphoric acid In tetrahydrofuran33%

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