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
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inquiryWe 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
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inquiryBedaquiline CAS No.:843663-66-1 Name: Bedaquiline Synonyms: 6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol
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inquiry1. 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
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inquiryCangzhou 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
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
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
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inquiryHenan 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
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inquiry1. 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
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inquiryTMC-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
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inquiryPRODUCT DETAILS
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inquiryHenan 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
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inquiryAppearance: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.
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inquiryCompany 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
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inquiryA 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
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inquiryMassive 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
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inquiryZibo 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
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inquiryTMC-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(
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
(3S,4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl-4-methylbenzenesulfonate
dimethyl amine
bedaquiline
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide at 40℃; for 10h; Inert atmosphere; | 62% |
bedaquiline
Conditions | Yield |
---|---|
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
bedaquiline
Conditions | Yield |
---|---|
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
A
bedaquiline
B
1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
dimethyl amine
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 45℃; for 24h; |
ethyl (E)-3-(6-bromo-2-chloroquinolin-3-yl)acrylate
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
A
bedaquiline
B
1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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 |
A
bedaquiline
B
1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
A
bedaquiline
B
1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
Conditions | Yield |
---|---|
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
3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
A
bedaquiline
Conditions | Yield |
---|---|
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 |
bedaquiline
Conditions | Yield |
---|---|
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
bedaquiline
Conditions | Yield |
---|---|
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
3-(dimethylamino)-1-(naphthalen-2-yl)propan-1-one
bedaquiline
Conditions | Yield |
---|---|
With acetic acid; lithium diisopropyl amide In tetrahydrofuran at -80 - -70℃; Inert atmosphere; | 9.45 g |
3-benzyl-6-bromo-2-methoxyquinoline
3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
A
bedaquiline
Conditions | Yield |
---|---|
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
bedaquiline
Conditions | Yield |
---|---|
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
citric acid
Conditions | Yield |
---|---|
In isopropyl alcohol at 50 - 80℃; for 1h; | 96.6% |
bedaquiline
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; triethylamine In tetrahydrofuran at 30℃; under 760.051 Torr; for 4h; Solvent; Temperature; | 90% |
bedaquiline
(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
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
citric acid
Conditions | Yield |
---|---|
In isopropyl alcohol | 37% |
bedaquiline
tartaric acid
Conditions | Yield |
---|---|
In acetonitrile | 34% |
bedaquiline
Conditions | Yield |
---|---|
With sulfuric acid In isopropyl alcohol | 33% |
bedaquiline
Conditions | Yield |
---|---|
With phosphoric acid In tetrahydrofuran | 33% |
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