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Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem's R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. DayangChem can provide different quantities

6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol

Cas:843663-66-1

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

We can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need CMO

Bedaquiline manufacturer/supplier

Cas:843663-66-1

Min.Order:1 Gram

Negotiable

Type:Manufacturers

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Wuhan Fortuna Chemical Co.,Ltd

Unique advantages Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White to off-white powder Storage:cool dry place Package:1kg/foil bag;25kg/drum Application:medicine raw material

Manufacturer high quality Bedaquiline Cas 843663-66-1 with good price

Cas:843663-66-1

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

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Hangzhou Think Chemical Co. Ltd

Bedaquiline CAS No.:843663-66-1 Name: Bedaquiline Synonyms: 6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol

High purity Bedaquiline CAS No.:843663-66-1

Cas:843663-66-1

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Factory Price API 99% TMC-207 843663-66-1 GMP Manufacturer

Cas:843663-66-1

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

Cangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing

bedaquinline

Cas:843663-66-1

Min.Order:1 Gram

FOB Price: $10.0

Type:Manufacturers

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ANQING CHICO PHARMACEUTICAL CO.,LTD.

High quality. Factory supply. In stock. Best price.1.Quick response within 24 hours;2.Best quality in your requirement;?3.We pay more attention on delivery time, and usually ship on time;4.Under the premise of safety and effectiveness, we can produce

Bedaquiline

Cas:843663-66-1

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

(αS,βR)-Bedaquiline

Cas:843663-66-1

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

Henan Tianfu Chemical Co., Ltd. is located in Zhengzhou High-tech Development Zone with import and export license. We passed ISO 9001:2008 in 2009, and won "High-tech Enterprise" by provincial government in 2013.The objective of the com

TIANFU-CHEM - TMC-207

Cas:843663-66-1

Min.Order:1 Gram

FOB Price: $1000.0

Type:Lab/Research institutions

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Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

New production CAS 843663-66-1 with best quality

Cas:843663-66-1

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages ♦ High purity, all above 98.5%, no impurities after the dissolution ♦ We will test each batch to ensure quality ♦ OEM and private brand services designed for free ♦ Various cap colors available &diam

TMC-207 CAS843663-66-1

Cas:843663-66-1

Min.Order:1 Metric Ton

FOB Price: $7.0 / 10.0

Type:Trading Company

inquiry

Shanghai Upbio Tech Co.,Ltd

1.In No Less 10 years exporting experience. you can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specializ

6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol

Cas:843663-66-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

bedaquinline 99%

Cas:843663-66-1

Min.Order:1 Kilogram

FOB Price: $86.0 / 100.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

TMC-207 CAS:843663-66-1 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates, s

TMC-207 CAS:843663-66-1

Cas:843663-66-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol

Cas:843663-66-1

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Leader Biochemical Group

PRODUCT DETAILS

China Largest Manufacturer factory sales Bedaquiline/TMC-207 CAS 843663-66-1

Cas:843663-66-1

Min.Order:500 Kilogram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol

Cas:843663-66-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Wuhan BJM Pharm Inc.

Appearance:White powder Storage:should be stored in a well-closed container at low temperature, keep away from moisture, heat and light. Package:NW 1kg/foil bag; 20-25kg/drum or carton Application:Chemical raw materials, pharmaceutical intermediate.

TMC-207

Cas:843663-66-1

Min.Order:1 Kilogram

FOB Price: $20.0

Type:Other

inquiry

Triumph International Development Limilted

Appearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:As

Bedaquiline

Cas:843663-66-1

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

R-207910 Bedaquiline 843663-66-1

Cas:843663-66-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Bedaquiline / 99% / 843663-66-1 in sock

Cas:843663-66-1

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

BEDAQUILINE

Cas:843663-66-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Miheng Trading Co., Ltd.

TMC-207 CAS 843663-66-1 Our advantage 1.Top quality: Using high quality material and establishing a strict quality control system,assigning specific persons in charge of each part of production,from raw material purchase to assembly. 2 Prof

TMC-207 CAS 843663-66-1

Cas:843663-66-1

Min.Order:1 Kilogram

FOB Price: $50.0 / 100.0

Type:Trading Company

inquiry

SHANGHAI T&W PHARMACEUTICAL CO., LTD.

A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc

Bedaquiline

Cas:843663-66-1

Min.Order:4 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

TMC-207

Cas:843663-66-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hefei Zhaobo Technology Co., Ltd.

TMC-207 CAS 843663-66-1 Purity: 99% Min Application: Intermediates Appearance: Powder Package: Bag Delivery: 3-5days Our Advantage & Service 1.Top quality: Using high quality material and establishing a strict quality control system,

TMC-207 CAS 843663-66-1

Cas:843663-66-1

Min.Order:1 Kilogram

FOB Price: $10.0 / 50.0

Type:Trading Company

inquiry

Shanghai Massive Chemical Technology Co., Ltd.

Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and

bedaquiline/High quality/Best price

Cas:843663-66-1

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol

Cas:843663-66-1

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Hangzhou Lingrui Chemical Co.,Ltd.

TMC-207Appearance:White or Almost White crystalline powder Storage:Store in refrigerator Package:according to customers' requirements Application:Steroids injection For Body building Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by sea(

TMC-207

Cas:843663-66-1

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

TaiChem Taizhou Limited

Established in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site

TMC-207

Cas:843663-66-1

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic 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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