1. We integrate research and development, production, and sales. A 1800 square meter research and development center,The company has conducted over 50 research and development and technical service projects annually, applied for more than 10 patents,
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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/917.html Product Name (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium (2R)-hydroxy(phenyl)eth
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inquiryDayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe
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inquiryItems Standard Result Appearance White or off-white solid Conforms Identification HNMR
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inquiry(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate CAS 376608-71-8 Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical & its i
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inquiryhigh quality Appearance:White or off white powder Storage:Sealed, dry, microtherm , avoid light and smell Package:According to the demand of customer Application:Pharmaceutical intermediates Transportation:by air or by sea Port:shanghai
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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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inquiryAs a leading and professional manufacturer of APIs and API intermediates in China,Anhui Dexinjia Biopharm Co., Ltd founded in 2006, Except for the R&D center, our company has built a close cooperation relation with Chinese Academy of Sciences,
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inquiry1. made in GMP plant, commerially 2. Normal Stock: 500kgs 3. Audit accepted. Related documents are available to offer and audited by many clients, such as Lupin, MSN, Dr reddy etc 4. Chromatographic Purity (HPLC): not less than 99.0% Appearan
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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 new ap
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inquiry
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inquiry(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate Basic information Product Name: (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate Synonyms: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanamine(S
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inquiryLIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc.
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inquiry(1R,2R)-2-(3,4-difluorophenyl)cyclopropanamine(S)-(carboxylato(phenyl)methyl)holmium Basic information Product Name: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanamine(S)-(carboxylato(phenyl)methyl)holmium
Our Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con
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inquiryWITH 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
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inquiryName (1R,2R)-2-(3,4-difluorophenyl) cyclopropanamine(S)-(carboxylato(phenyl) methyl)holmium CAS No. 376608-71-8 MF C17H17F2NO3 Purity 99%
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inquiry1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Solid Storage:Store in sealed contai
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inquiry1.No Less 8 years exporting experience. Clients 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 Specialized
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inquiry(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine (2R)-Hydroxy(phenyl)ethanoate CAS:376608-71-8 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical
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Min.Order:1 Gram
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inquiryHebei Mojin Biotechnology Co., Ltd, Our company is a professional chemical raw materials and chemical reagents research and development production enterprises. We have several production line,So we can control the lowest price. We also have several
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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 or off-white Solid 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:Common products:Se
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inquiryWe are concentrating on APIs and pharmaceutical intermediates. With in depth knowledge and understanding in this industry, we are indulged in supplying a wide assortments of pharmaceutical intermediates from Wuhan, Hubei, China. It is made ob
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inquirySpecification:USP/EP Month production ablity:50kg/Month Low price& High quality Manufacturer Appearance:white powder Storage:Room Temperature Application:376608-71-8
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inquiryWhy is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 2) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days. 4) We have warehouse in USA with quickly shipment . 5) We c
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inquiryHangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det
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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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Min.Order:1 Gram
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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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Min.Order:4 Kilogram
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inquiryJ&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
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inquirytrans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid
(R)-Mandelic Acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Stage #1: trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid With pyridine; thionyl chloride In toluene at 70℃; for 4h; Stage #2: With sodium azide; tetrabutylammomium bromide; sodium carbonate In water; toluene at 0℃; for 2h; Stage #3: (R)-Mandelic Acid In ethyl acetate at 17 - 25℃; for 3h; | 82% |
(R)-Mandelic Acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
In Isopropyl acetate at 0 - 20℃; for 4h; | 70.1% |
In methanol at 20 - 25℃; for 14h; | 46.4% |
In methanol at 20 - 25℃; for 12h; |
trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane
(R)-Mandelic Acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane With hydrogenchloride; zinc In methanol; water at -5 - 0℃; Stage #2: With ammonia In dichloromethane; water at 30℃; for 0.25h; Stage #3: (R)-Mandelic Acid In methanol at 20 - 25℃; | 36.61% |
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane With hydrogenchloride; zinc In deuteromethanol at -5 - 0℃; Stage #2: (R)-Mandelic Acid In methanol at 0 - 25℃; for 14h; | 36.61% |
ortho-difluorobenzene
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / dichloromethane / 4 h / 20 - 25 °C / Industry scale 2.1: sodium iodide; 3,5-dihydroxyphenol; sodium nitrite / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 3.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / toluene / 25 - 40 °C / Inert atmosphere 4.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 5.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 5.2: 0.25 h / 30 °C 5.3: 20 - 25 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: aluminum (III) chloride / dichloromethane / 30 h / 20 - 25 °C / Industry scale 2.1: sodium iodide; sodium azide; 3,5-dihydroxyphenol / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 3.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene / 1.5 h / 15 - 20 °C / Inert atmosphere 4.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 5.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 5.2: 0.25 h / 10 - 30 °C 6.1: methanol / 12 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / dichloromethane / 20 - 25 °C / Large scale 2.1: sodium nitrite; 3,5-dihydroxyphenol; sodium iodide / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 3.1: borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 25 - 30 °C / Inert atmosphere 4.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / 0 - 10 °C 5.1: hydrogenchloride; zinc / deuteromethanol / -5 - 0 °C 5.2: 14 h / 0 - 25 °C View Scheme |
3-chloro-1-(3',4'-difluorophenyl)-propan-1-one
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium iodide; 3,5-dihydroxyphenol; sodium nitrite / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / toluene / 25 - 40 °C / Inert atmosphere 3.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 4.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 4.2: 0.25 h / 30 °C 4.3: 20 - 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium iodide; sodium azide; 3,5-dihydroxyphenol / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene / 1.5 h / 15 - 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 4.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 4.2: 0.25 h / 10 - 30 °C 5.1: methanol / 12 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium nitrite; 3,5-dihydroxyphenol; sodium iodide / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 2.1: borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 25 - 30 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / 0 - 10 °C 4.1: hydrogenchloride; zinc / deuteromethanol / -5 - 0 °C 4.2: 14 h / 0 - 25 °C View Scheme |
1-(3',4'-difluorophenyl)-3-nitro-propan-1-one
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / toluene / 25 - 40 °C / Inert atmosphere 2.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 3.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 3.2: 0.25 h / 30 °C 3.3: 20 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene / 1.5 h / 15 - 20 °C / Inert atmosphere 2.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 3.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 3.2: 0.25 h / 10 - 30 °C 4.1: methanol / 12 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 25 - 30 °C / Inert atmosphere 2.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / 0 - 10 °C 3.1: hydrogenchloride; zinc / deuteromethanol / -5 - 0 °C 3.2: 14 h / 0 - 25 °C View Scheme |
(1S)-1-(3,4-difluorophenyl)-3-nitropropan-1-ol
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 2.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 2.2: 0.25 h / 10 - 30 °C 3.1: methanol / 12 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / 0 - 10 °C 2.1: hydrogenchloride; zinc / deuteromethanol / -5 - 0 °C 2.2: 14 h / 0 - 25 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 1.2: 0.25 h / 10 - 30 °C 2.1: methanol / 12 h / 20 - 25 °C View Scheme |
(E)-methyl 3-(3,4-difluorophenyl)acrylate
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / dimethyl sulfoxide / 0.5 h / 25 °C 1.2: 16 h / 0 - 25 °C 2.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 3.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 4.1: toluene / 1 h / 110 °C 4.2: 2 h / 100 °C 4.3: 25 °C / pH 10 5.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
(E)-3-(3,4-difluorophenyl)acrylic acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sulfuric acid / 72 h / 60 °C 2.1: sodium hydride / dimethyl sulfoxide / 0.5 h / 25 °C 2.2: 16 h / 0 - 25 °C 3.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 4.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 5.1: toluene / 1 h / 110 °C 5.2: 2 h / 100 °C 5.3: 25 °C / pH 10 6.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: oxalyl dichloride / dichloromethane / 0 h / 25 - 30 °C 1.2: 0 h / 25 - 30 °C 2.1: pyridine / acetone / 0 h / 0 - 30 °C 2.2: 0 - 5 °C 3.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 3.2: 3 h / 25 - 30 °C 4.1: hydrazine hydrate / methanol / 12 h / 60 - 65 °C 5.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 6.1: toluene / 1 h / 110 °C 6.2: 2 h / 100 °C 6.3: 25 °C / pH 10 7.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: oxalyl dichloride / dichloromethane / 0 h / 25 - 30 °C 1.2: 0 h / 25 - 30 °C 2.1: pyridine / acetone / 0 h / 0 - 30 °C 2.2: 0 - 5 °C 3.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 3.2: 3 h / 25 - 30 °C 4.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 6.1: hydrazine hydrate / 1,4-dioxane / 3 h / 65 °C 7.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 8.1: toluene / 1 h / 110 °C 8.2: 2 h / 100 °C 8.3: 25 °C / pH 10 9.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: oxalyl dichloride / dichloromethane / 0 h / 25 - 30 °C 1.2: 0 h / 25 - 30 °C 2.1: pyridine / acetone / 0 h / 0 - 30 °C 2.2: 0 - 5 °C 3.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 3.2: 3 h / 25 - 30 °C 4.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 5.1: sulfuric acid / 2 h / 60 °C 6.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 7.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 8.1: toluene / 1 h / 110 °C 8.2: 2 h / 100 °C 8.3: 25 °C / pH 10 9.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 2.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 3.1: toluene / 1 h / 110 °C 3.2: 2 h / 100 °C 3.3: 25 °C / pH 10 4.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 2.1: toluene / 1 h / 110 °C 2.2: 2 h / 100 °C 2.3: 25 °C / pH 10 3.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
(2E)-3-(3,4-difluorophenyl)acryloylchloride
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: pyridine / acetone / 0 h / 0 - 30 °C 1.2: 0 - 5 °C 2.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 2.2: 3 h / 25 - 30 °C 3.1: hydrazine hydrate / methanol / 12 h / 60 - 65 °C 4.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 5.1: toluene / 1 h / 110 °C 5.2: 2 h / 100 °C 5.3: 25 °C / pH 10 6.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: pyridine / acetone / 0 h / 0 - 30 °C 1.2: 0 - 5 °C 2.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 2.2: 3 h / 25 - 30 °C 3.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 5.1: hydrazine hydrate / 1,4-dioxane / 3 h / 65 °C 6.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 7.1: toluene / 1 h / 110 °C 7.2: 2 h / 100 °C 7.3: 25 °C / pH 10 8.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: pyridine / acetone / 0 h / 0 - 30 °C 1.2: 0 - 5 °C 2.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 2.2: 3 h / 25 - 30 °C 3.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 4.1: sulfuric acid / 2 h / 60 °C 5.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 6.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 7.1: toluene / 1 h / 110 °C 7.2: 2 h / 100 °C 7.3: 25 °C / pH 10 8.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
(E)-3-(3,4-difluorophenyl)-N-methoxy-N-methyl-prop-2-enamide
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 1.2: 3 h / 25 - 30 °C 2.1: hydrazine hydrate / methanol / 12 h / 60 - 65 °C 3.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 4.1: toluene / 1 h / 110 °C 4.2: 2 h / 100 °C 4.3: 25 °C / pH 10 5.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 1.2: 3 h / 25 - 30 °C 2.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 4.1: hydrazine hydrate / 1,4-dioxane / 3 h / 65 °C 5.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 6.1: toluene / 1 h / 110 °C 6.2: 2 h / 100 °C 6.3: 25 °C / pH 10 7.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 1.2: 3 h / 25 - 30 °C 2.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 3.1: sulfuric acid / 2 h / 60 °C 4.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 5.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 6.1: toluene / 1 h / 110 °C 6.2: 2 h / 100 °C 6.3: 25 °C / pH 10 7.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrazine hydrate / methanol / 12 h / 60 - 65 °C 2.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 3.1: toluene / 1 h / 110 °C 3.2: 2 h / 100 °C 3.3: 25 °C / pH 10 4.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 3.1: hydrazine hydrate / 1,4-dioxane / 3 h / 65 °C 4.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 5.1: toluene / 1 h / 110 °C 5.2: 2 h / 100 °C 5.3: 25 °C / pH 10 6.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 2.1: sulfuric acid / 2 h / 60 °C 3.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 4.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 5.1: toluene / 1 h / 110 °C 5.2: 2 h / 100 °C 5.3: 25 °C / pH 10 6.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
(R)-Mandelic Acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
In methanol at 18 - 45℃; for 2.5h; | 7.56 g |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: toluene / 1 h / 110 °C 1.2: 2 h / 100 °C 1.3: 25 °C / pH 10 2.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrazine hydrate / 1,4-dioxane / 3 h / 65 °C 2.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 3.1: toluene / 1 h / 110 °C 3.2: 2 h / 100 °C 3.3: 25 °C / pH 10 4.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sulfuric acid / 2 h / 60 °C 2.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 3.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 4.1: toluene / 1 h / 110 °C 4.2: 2 h / 100 °C 4.3: 25 °C / pH 10 5.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 2.1: hydrazine hydrate / 1,4-dioxane / 3 h / 65 °C 3.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 4.1: toluene / 1 h / 110 °C 4.2: 2 h / 100 °C 4.3: 25 °C / pH 10 5.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
2-chloro-1-(3,4-difluorophenyl)ethan-1-one
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: N,N-diethylaniline hydrochloride; sodium tetrahydroborate; (S)-diphenylprolinol / chloroform; 1,2-dimethoxyethane / 2 h / 0 - 30 °C 2.1: potassium tert-butylate / toluene / 30 h / 30 - 50 °C 3.1: thionyl chloride / toluene / 2 h / Reflux 3.2: 15 - 30 °C 4.1: sodium hydroxide; sodium hypochlorite / 16 h / 25 - 40 °C 5.1: Isopropyl acetate / 4 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane-THF / toluene / 3 h / 10 °C / Inert atmosphere 2.1: sodium t-butanolate / toluene / 2 h / 20 °C 2.2: 25 h / 40 - 60 °C 3.1: ammonia; Methyl formate; sodium methylate / methanol / 10 h / 70 °C / 1500.15 Torr 4.1: sodium hydroxide; sodium hypochlorite / water / 2 h / 0 - 55 °C 5.1: methanol / 14 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: (S)-5,5-diphenyl-2-methoxy-3,4-propano-1,3,2-oxazaborolidine; dimethylsulfide borane complex / 1 h / 15 °C 2.1: sodium t-butanolate / toluene / 2 h / 20 °C 2.2: 25 h / 40 - 60 °C 3.1: ammonia; Methyl formate; sodium methylate / methanol / 10 h / 70 °C / 1500.15 Torr 4.1: sodium hydroxide; sodium hypochlorite / water / 2 h / 0 - 55 °C 5.1: methanol / 14 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; Trimethyl borate; (S)-diphenylprolinol / toluene / 0.97 h / 38 °C / Inert atmosphere 2.1: sodium t-butanolate / toluene / 13 h / 38 - 58 °C 3.1: sodium hydroxide / water / 1.5 h / 48 °C 4.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1.5 h / 30 °C 4.2: 1.5 h 5.1: sodium hydroxide; sodium hypochlorite / water / 4.5 h / 20 - 38 °C 5.2: 1.5 h View Scheme |
(1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium tert-butylate / toluene / 30 h / 30 - 50 °C 2.1: thionyl chloride / toluene / 2 h / Reflux 2.2: 15 - 30 °C 3.1: sodium hydroxide; sodium hypochlorite / 16 h / 25 - 40 °C 4.1: Isopropyl acetate / 4 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium t-butanolate / toluene / 2 h / 20 °C 1.2: 25 h / 40 - 60 °C 2.1: ammonia; Methyl formate; sodium methylate / methanol / 10 h / 70 °C / 1500.15 Torr 3.1: sodium hydroxide; sodium hypochlorite / water / 2 h / 0 - 55 °C 4.1: methanol / 14 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium t-butanolate / toluene / 13 h / 38 - 58 °C 2.1: sodium hydroxide / water / 1.5 h / 48 °C 3.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1.5 h / 30 °C 3.2: 1.5 h 4.1: sodium hydroxide; sodium hypochlorite / water / 4.5 h / 20 - 38 °C 4.2: 1.5 h View Scheme |
trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / toluene / 2 h / Reflux 1.2: 15 - 30 °C 2.1: sodium hydroxide; sodium hypochlorite / 16 h / 25 - 40 °C 3.1: Isopropyl acetate / 4 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1.5 h / 30 °C 1.2: 1.5 h 2.1: sodium hydroxide; sodium hypochlorite / water / 4.5 h / 20 - 38 °C 2.2: 1.5 h View Scheme |
(1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid ethyl ester
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: ammonia; Methyl formate; sodium methylate / methanol / 10 h / 70 °C / 1500.15 Torr 2: sodium hydroxide; sodium hypochlorite / water / 2 h / 0 - 55 °C 3: methanol / 14 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 1.5 h / 48 °C 2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1.5 h / 30 °C 2.2: 1.5 h 3.1: sodium hydroxide; sodium hypochlorite / water / 4.5 h / 20 - 38 °C 3.2: 1.5 h View Scheme |
(1R,2R)-trans-2(3,4-difluorophenyl)cyclopropyl carboxamide
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; sodium hypochlorite / water / 2 h / 0 - 55 °C 2: methanol / 14 h / 20 - 25 °C View Scheme |
(1R,2R)-trans-2(3,4-difluorophenyl)cyclopropyl carboxamide
(R)-Mandelic Acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Stage #1: (1R,2R)-trans-2(3,4-difluorophenyl)cyclopropyl carboxamide With sodium hypochlorite; sodium hydroxide In water at 20 - 38℃; for 4.5h; Stage #2: (R)-Mandelic Acid In ethanol for 1.5h; Temperature; |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
di-tert-butyl dicarbonate
(tert-butyl (1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate
Conditions | Yield |
---|---|
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt With N-ethyl-N,N-diisopropylamine In dichloromethane at 10 - 20℃; for 1h; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 10 - 20℃; for 4h; Solvent; | 99% |
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt With N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 25℃; for 0.5h; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20 - 25℃; for 3h; | 94.51% |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
9-[(1’R,2’S,3’S,4’S)-2’,3’-dihydroxyl-4'-hydroxyethoxycyclopenta-1'-yl]-9H-2-thiopropyl-6-chloro-8-azepine
ticagrelor
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In 2-methyltetrahydrofuran at 20 - 30℃; for 3h; Reagent/catalyst; Solvent; | 87% |
With potassium carbonate In acetonitrile at 25 - 30℃; | 62.19% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 25 - 30℃; for 4h; | 2.29 g |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
[3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; | 84% |
With potassium carbonate In toluene at 30℃; for 24h; | 81.31% |
With potassium carbonate In water at 30℃; Product distribution / selectivity; |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt; C15H16F3N3OS With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 2h; Molecular sieve; Stage #2: With hydrogenchloride In diethyl ether; dichloromethane at 20℃; for 0.5h; | 79% |
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt; C15H16F3N3OS With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 2h; Molecular sieve; Stage #2: With hydrogenchloride In diethyl ether; dichloromethane at 20℃; for 0.5h; | 79% |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
N-tert-butyloxycarbonylpiperidin-4-one
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 5h; | 78% |
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 5h; | 78% |
4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
With triethylamine In 1,2-dimethoxyethane at 100℃; for 7h; | 68% |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt; C14H14F3N3OS With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 3h; Molecular sieve; Stage #2: With hydrogenchloride In diethyl ether; dichloromethane at 20℃; for 0.5h; | 54% |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt; C14H14F3N3OS With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 3h; Stage #2: With hydrogenchloride In diethyl ether; dichloromethane at 20℃; for 0.5h; | A 54% B 34% |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
tert butyl 4-formylpiperidine-1-carboxylate
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In methanol at 0℃; for 2h; | 45% |
With sodium cyanoborohydride; acetic acid In methanol for 2h; Cooling with ice; | 45% |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt; C14H14F3N3OS With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 3h; Molecular sieve; Stage #2: With hydrogenchloride In diethyl ether; dichloromethane at 20℃; for 0.5h; | 34% |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
[3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 6.1: iodine / acetone / 2 h / 25 - 60 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
ticagrelor
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 6.1: hydrogenchloride; water / toluene; methanol / 2 h / 25 - 30 °C 6.2: pH > 8 View Scheme | |
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 6.1: potassium carbonate / acetone / 24 h / 25 - 60 °C 7.1: hydrogenchloride; water / methanol / 5.5 h / 20 - 55 °C 7.2: 25 - 30 °C / pH 10 View Scheme | |
Multi-step reaction with 9 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 6.1: iodine / acetone / 2 h / 25 - 60 °C 7.1: potassium carbonate / acetone / 20 h / 55 - 60 °C 8.1: hydrogenchloride; water / methanol / 5 h / 20 - 25 °C 8.2: 25 - 30 °C / pH 10 9.1: formic acid / palladium 10% on activated carbon / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 20 °C 1.2: 4 h / 10 - 20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -80 - -75 °C / Inert atmosphere 3.1: potassium carbonate / tetrahydrofuran / 3 h / 10 - 20 °C / pH 9 4.1: zinc; acetic acid / dichloromethane / 2 h / 5 - 10 °C 4.2: 2 h / 0 - 3 °C 4.3: 4 h View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
tert-butyl (6-chloro-5-nitro-2-(propylthio)pyrimidin-4-yl)((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h View Scheme | |
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 20 °C 1.2: 4 h / 10 - 20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -80 - -75 °C / Inert atmosphere View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
2-[[(3aR,4S,6R,6aS)-6-[[4-[N-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-yl]-N-tert-butoxycarbonyl]amino]-2-(propylthio)-5-nitropyrimidin-6-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy] ethanol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 10 - 20 °C 1.2: 4 h / 10 - 20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -80 - -75 °C / Inert atmosphere 3.1: potassium carbonate / tetrahydrofuran / 3 h / 10 - 20 °C / pH 9 View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
2-[[(3aR,4S,6R,6aS)-6-[[4-[N-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-yl]-N-tert-butoxycarbonyl]amino]-2-(propylthio)-5-aminopyrimidin-6-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]ethanol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
tert-butyl N-[3-[(3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-5-(propylsulfanyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-N-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 6.1: iodine / acetone / 2 h / 25 - 60 °C 7.1: potassium carbonate / acetone / 20 h / 55 - 60 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
C30H34F2N6O4S
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 6.1: iodine / acetone / 2 h / 25 - 60 °C 7.1: potassium carbonate / acetone / 20 h / 55 - 60 °C 8.1: hydrogenchloride; water / methanol / 5 h / 20 - 25 °C 8.2: 25 - 30 °C / pH 10 View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
2-({(3aR,45,6R,6aS)-6-[7-{[[N-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-tert-butoxycarbonyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)-O-tertbutoxycarbonylethanol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 - 25 °C 1.2: 3 h / 20 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -25 - -15 °C 2.2: 1.5 h / -25 - -15 °C 2.3: 0.08 h 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C 4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C 5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C 6.1: potassium carbonate / acetone / 24 h / 25 - 60 °C View Scheme |
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