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
Cas:477600-74-1
Min.Order:1 Gram
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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
Cas:477600-74-1
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Type:Manufacturers
inquiryHigh 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
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inquiryDayangchem'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
Cas:477600-74-1
Min.Order:1 Kilogram
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Type:Lab/Research institutions
inquiryOur 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
Cas:477600-74-1
Min.Order:5 Kiloliter
FOB Price: $1.2 / 5.0
Type:Manufacturers
inquiryOur advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva
Cas:477600-74-1
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Type:Trading Company
inquiryOur company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O
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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
Cas:477600-74-1
Min.Order:1 Kilogram
FOB Price: $139.0 / 210.0
Type:Trading Company
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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inquiryOur 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
Cas:477600-74-1
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FOB Price: $89.0 / 100.0
Type:Trading Company
inquiryN-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine CAS:477600-74-1 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemic
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Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryHello, 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
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inquiryAdvantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&
Cas:477600-74-1
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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 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
Cas:477600-74-1
Min.Order:100 Gram
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Type:Lab/Research institutions
inquiry1,we produce and sell good chemicals around the world. 2,our success rate is about 95%. this means, if customer order is accepted, the probability that the customer will obtain the ordered substances, is 95%. 3,our staff consists of highly qualifie
Cas:477600-74-1
Min.Order:1 Kilogram
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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
Cas:477600-74-1
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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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Type:Lab/Research institutions
inquiryPacking: According to customer requirements Delivery time: In stock or depands Port of shipment: Ningbo/Shanghai/Qingdao OEM/ODM:Welcome Sample:We can offer our existing samples at once Transportation:Express/Sea/Air Port:Ningbo/Shanghai/Qingd
Cas:477600-74-1
Min.Order:0
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Type:Trading Company
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
Cas:477600-74-1
Min.Order:0
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inquiryChemlyte Solutions believe that customers and suppliers deserve much more than what traditional distributors can offer. To grow in today s fast-paced and increasingly competitive market it is essential to be able to quickly adapt to market forces eff
Cas:477600-74-1
Min.Order:100 Gram
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Type:Other
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
Cas:477600-74-1
Min.Order:10 Gram
Negotiable
Type:Lab/Research institutions
inquiryProduct Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,
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Min.Order:1 Kilogram
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Type:Lab/Research institutions
inquiryProduct name: N-Methyl-N-[(3R,4R)-4-Methylpiperidin-3-yl]-7H-Pyrrolo[2,3-d]Pyrimidin-4-Amine CAS No.:477600-74-1 Molecule Formula:C13H19N5 Molecule Weight:245.32 Purity: 99.0% Package: 25kg/drum Description:White crystalline powder Manufacture
Cas:477600-74-1
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiryOur Advantages A. International Top level TechnologyOur company owned biomedicine experts are famous at home and abroad with rich experience in research and development in the field of efficient chiral functional molecules research and development an
Cas:477600-74-1
Min.Order:0
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Type:Trading Company
inquiryGMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,
Cas:477600-74-1
Min.Order:1 Milligram
Negotiable
Type:Trading Company
inquiryfactory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B
Cas:477600-74-1
Min.Order:1 Kilogram
FOB Price: $18.0 / 20.0
Type:Trading Company
inquiryN-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Basic information Product Name: N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Synonyms: N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-
Cas:477600-74-1
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiryShandong Mopai Biotechnology 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 chemicals. W
Cas:477600-74-1
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiry1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer
Cas:477600-74-1
Min.Order:1 Metric Ton
FOB Price: $1.5
Type:Trading Company
inquirytert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In water at 65 - 75℃; under 1551.49 Torr; for 3h; Inert atmosphere; | 96% |
With triethylsilane; 5%-palladium/activated carbon; acetic acid In methanol at 30℃; for 0.166667h; | 93.1% |
With 10 wt% Pd(OH)2 on carbon; hydrazine hydrate; acetic acid In ethanol at 70 - 75℃; for 2h; Reagent/catalyst; | 75.8% |
(3R,4R)-tert-butyl 4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With zinc dibromide In dichloromethane for 12h; | 95% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal; hydrogen In methanol at 45℃; under 6000.6 Torr; | 93% |
With 20% palladium hydroxide-activated charcoal; ammonium formate In methanol at 60℃; for 6h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; | 93.3% |
With 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid In methanol; water at 50℃; under 3000.3 - 4500.45 Torr; for 12h; | 92.38% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane; water at 20℃; for 1h; | 91% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In ethanol at 60 - 70℃; | 85% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With sulfuric acid at 90℃; | 28.9% |
(S)-5-hydroxypiperidin-2-one
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: 1H-imidazole / 24.5 h / 5 - 20 °C 2.1: 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 2 h 3.1: n-butyllithium; hexamethyldisilazan / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.2: 2 h / -78 °C 4.1: magnesium / diethyl ether 4.2: 0.25 h / -20 °C 4.3: 2 h / 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 7.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C 8.1: zinc dibromide / dichloromethane / 12 h View Scheme |
(5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium / tetrahydrofuran / 1 h / -78 °C 1.2: 2 h 2.1: n-butyllithium; hexamethyldisilazan / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 2 h / -78 °C 3.1: magnesium / diethyl ether 3.2: 0.25 h / -20 °C 3.3: 2 h / 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 6.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C 7.1: zinc dibromide / dichloromethane / 12 h View Scheme |
7-deazaadenine
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: water; acetonitrile / 0.25 h / 20 °C 1.2: 1 h 2.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C 3.1: zinc dibromide / dichloromethane / 12 h View Scheme |
tert-butyl (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one-1-carboxylate
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: n-butyllithium; hexamethyldisilazan / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 2 h / -78 °C 2.1: magnesium / diethyl ether 2.2: 0.25 h / -20 °C 2.3: 2 h / 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 5.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C 6.1: zinc dibromide / dichloromethane / 12 h View Scheme |
tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: magnesium / diethyl ether 1.2: 0.25 h / -20 °C 1.3: 2 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C 5.1: zinc dibromide / dichloromethane / 12 h View Scheme |
(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 3: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C 4: zinc dibromide / dichloromethane / 12 h View Scheme |
tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C 3: zinc dibromide / dichloromethane / 12 h View Scheme |
tert-butyl (3S,4R)-3-hydroxy-4-methyl-piperidine-1-carboxylate
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C 2: zinc dibromide / dichloromethane / 12 h View Scheme | |
Multi-step reaction with 3 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / 1,4-dioxane / 4 h / 0 - 90 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 24 h / 20 °C 3.1: hydrogenchloride / tetrahydrofuran / 1 h / 20 °C View Scheme |
methyl-(1-trityl-4-methylpiperidin-3-yl)carbamate
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 2.1: ethyl acetate / 3 h / 25 - 30 °C 3.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 4.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 5.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 5.2: Reflux View Scheme | |
Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 2.1: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3 3.1: water; methanol / 8 - 9 h / 20 - 70 °C 4.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 5.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 6.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 6.2: Reflux View Scheme | |
Multi-step reaction with 7 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 2: ethyl acetate / 3 h / 25 - 30 °C 3: potassium carbonate / ethyl acetate; water / pH 9 - 10 4: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 5: sodium hydroxide / water; acetone / 55 - 60 °C 6: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 7: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: water; methanol / 8 - 9 h / 20 - 70 °C 2.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 3.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 4.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 4.2: Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate / water / pH 7 - 8 2.1: ethyl acetate / 3 h / 25 - 30 °C 3.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 4.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 5.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 5.2: Reflux View Scheme | |
Multi-step reaction with 6 steps 1: water; methanol / 8 - 9 h / 20 - 70 °C 2: potassium carbonate / ethyl acetate; water / pH 9 - 10 3: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 4: sodium hydroxide / water; acetone / 55 - 60 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 6: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
1-triryI-N,4-dimethylpiperidin-3-amine
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: ethyl acetate / 3 h / 25 - 30 °C 2.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 3.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 4.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 4.2: Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3 2.1: water; methanol / 8 - 9 h / 20 - 70 °C 3.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 4.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 5.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 5.2: Reflux View Scheme | |
Multi-step reaction with 6 steps 1: ethyl acetate / 3 h / 25 - 30 °C 2: potassium carbonate / ethyl acetate; water / pH 9 - 10 3: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 4: sodium hydroxide / water; acetone / 55 - 60 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 6: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 2.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 3.2: Reflux View Scheme | |
Multi-step reaction with 5 steps 1: potassium carbonate / ethyl acetate; water / pH 9 - 10 2: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 3: sodium hydroxide / water; acetone / 55 - 60 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 5: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme | |
Multi-step reaction with 5 steps 1: potassium carbonate / ethyl acetate; water / pH 9 - 10 2: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 3: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C 4: sodium hydroxide / water; acetone / 50 - 55 °C 5: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
(3R,4R)-1-trityl-N,4-dimethylpiperidin-3-amine
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 2.2: Reflux View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 2: sodium hydroxide / water; acetone / 55 - 60 °C 3: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 4: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C 3: sodium hydroxide / water; acetone / 50 - 55 °C 4: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
2,4-dichloro-7-p-methylbenzenesulfonyl-7H-pyrrole[2,3-d]pyrimidin-4-amine
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 70 - 75 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 2.2: Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 2.2: Reflux View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 70 - 75 °C 2: sodium hydroxide / water; acetone / 55 - 60 °C 3: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 4: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water; acetone / 2 - 3 h / 0 - 30 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 70 - 75 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 3.2: Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water; acetone / 2 - 3 h / 0 - 30 °C 2.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 3.2: Reflux View Scheme | |
Multi-step reaction with 5 steps 1: sodium hydroxide / water; acetone / 2 - 3 h / 0 - 30 °C 2: potassium carbonate / N,N-dimethyl-formamide / 10 h / 70 - 75 °C 3: sodium hydroxide / water; acetone / 55 - 60 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 5: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
C39H38ClN5O2S
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: C39H38ClN5O2S With palladium 10% on activated carbon; hydrogen In methanol at 45 - 55℃; under 3750.38 Torr; for 10h; Stage #2: With sodium hydroxide In methanol; water Reflux; | |
Multi-step reaction with 3 steps 1: sodium hydroxide / water; acetone / 55 - 60 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 3: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme | |
Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C 2: sodium hydroxide / water; acetone / 50 - 55 °C 3: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
C20H24ClN5O2S
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water; acetone / 50 - 55 °C 2: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
C32H32ClN5
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 2: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
N-((3R,4R)-4-methyl-piperidin-3-yl)-N-methyl-2-chloro-7H-pyrrolo[2,3-D]pyrimidine-4-amine
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With 10% palladium hydroxide on charcoal; hydrogen In methanol at 50 - 55℃; under 5250.53 - 6000.6 Torr; for 4h; Solvent; Reagent/catalyst; Temperature; Pressure; Time; | 25 g |
O-methyl-N-(4-methylpyridin-3-yl)carbamate
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr 2: triethylamine / acetonitrile / 10 h / 65 - 70 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 4: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3 5: water; methanol / 8 - 9 h / 20 - 70 °C 6: potassium carbonate / ethyl acetate; water / pH 9 - 10 7: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 8: sodium hydroxide / water; acetone / 55 - 60 °C 9: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 10: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme | |
Multi-step reaction with 10 steps 1: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr 2: triethylamine / acetonitrile / 10 h / 65 - 70 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 4: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3 5: water; methanol / 8 - 9 h / 20 - 70 °C 6: potassium carbonate / ethyl acetate; water / pH 9 - 10 7: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 8: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C 9: sodium hydroxide / water; acetone / 50 - 55 °C 10: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme | |
Multi-step reaction with 7 steps 1.1: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr 2.1: triethylamine / acetonitrile / 10 h / 65 - 70 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 4.1: ethyl acetate / 3 h / 25 - 30 °C 5.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 6.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 7.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 7.2: Reflux View Scheme |
3-amino-4-methylpyridine
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: potassium tert-butylate / 1 h / 10 - 15 °C 2: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr 3: triethylamine / acetonitrile / 10 h / 65 - 70 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 5: ethyl acetate / 3 h / 25 - 30 °C 6: potassium carbonate / ethyl acetate; water / pH 9 - 10 7: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 8: sodium hydroxide / water; acetone / 55 - 60 °C 9: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 10: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme | |
Multi-step reaction with 10 steps 1: potassium tert-butylate / 1 h / 10 - 15 °C 2: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr 3: triethylamine / acetonitrile / 10 h / 65 - 70 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 5: ethyl acetate / 3 h / 25 - 30 °C 6: potassium carbonate / ethyl acetate; water / pH 9 - 10 7: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 8: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C 9: sodium hydroxide / water; acetone / 50 - 55 °C 10: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme | |
Multi-step reaction with 11 steps 1: potassium tert-butylate / 1 h / 10 - 15 °C 2: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr 3: triethylamine / acetonitrile / 10 h / 65 - 70 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3 6: water; methanol / 8 - 9 h / 20 - 70 °C 7: potassium carbonate / ethyl acetate; water / pH 9 - 10 8: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 9: sodium hydroxide / water; acetone / 55 - 60 °C 10: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 11: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: triethylamine / acetonitrile / 10 h / 65 - 70 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 3.1: ethyl acetate / 3 h / 25 - 30 °C 4.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 5.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 6.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 6.2: Reflux View Scheme | |
Multi-step reaction with 7 steps 1.1: triethylamine / acetonitrile / 10 h / 65 - 70 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 3.1: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3 4.1: water; methanol / 8 - 9 h / 20 - 70 °C 5.1: potassium carbonate / ethyl acetate; water / pH 9 - 10 6.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 7.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr 7.2: Reflux View Scheme | |
Multi-step reaction with 8 steps 1: triethylamine / acetonitrile / 10 h / 65 - 70 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere 3: ethyl acetate / 3 h / 25 - 30 °C 4: potassium carbonate / ethyl acetate; water / pH 9 - 10 5: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C 6: sodium hydroxide / water; acetone / 55 - 60 °C 7: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C 8: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr View Scheme |
N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium carbonate / water / 48 h / 110 °C / Sealed tube 2: hydrogen; palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal / methanol / 45 °C / 6000.6 Torr View Scheme |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
formaldehyd
Conditions | Yield |
---|---|
With acetic acid; zinc In water at 20℃; Reagent/catalyst; Concentration; | 99.25% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
ethyl 2-cyanoacetate
citric acid
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In butan-1-ol at 80℃; for 0.166667h; | 96.4% |
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; ethyl 2-cyanoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In butan-1-ol at 40℃; for 20h; Inert atmosphere; Stage #2: citric acid In water; butan-1-ol at 22 - 81℃; for 2.5h; Inert atmosphere; | 93% |
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; ethyl 2-cyanoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In butan-1-ol at 35 - 45℃; for 7h; Inert atmosphere; Stage #2: citric acid In water; butan-1-ol at 20 - 90℃; Inert atmosphere; | 90.3% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
cyanoacetic acid
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Schlenk technique; | 96% |
With potassium carbonate; 4-pyrrolidin-1-ylpyridine; diisopropyl-carbodiimide In dichloromethane at 35℃; for 1h; pH=7 - 8; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Industrial scale; | 89.7% |
With 1,1'-carbonyldiimidazole In dichloromethane at 40℃; for 10h; | 89.21% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
ethyl 2-cyanoacetate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 5 - 20℃; for 8h; Temperature; Solvent; | 91% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20 - 30℃; for 24h; | 78% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60 - 65℃; Solvent; | 76.9% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
cycl-isopropylidene malonate
Conditions | Yield |
---|---|
In acetonitrile at 20℃; Solvent; Temperature; | 87.7% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
ethyl 2-cyanoacetate
Conditions | Yield |
---|---|
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; ethyl 2-cyanoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In butan-1-ol at 40℃; for 18h; Stage #2: With citric acid monohydrate In water; butan-1-ol at 80℃; for 0.5h; | 87.6% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
succinimidyl cyanoacetate
Conditions | Yield |
---|---|
In ethanol at 20℃; for 2h; | 86% |
In ethanol at 25℃; for 3h; Temperature; Time; | |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In toluene at 40℃; for 2h; Large scale; |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
diethyl malonate
Conditions | Yield |
---|---|
With triethylamine In methanol for 9h; Reflux; | 85% |
5-methyl-1,2-oxazole-4-carboxylic acid
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 3h; Inert atmosphere; Cooling with ice; Enzymatic reaction; | 80% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
cyanoacetic acid
Conditions | Yield |
---|---|
In acetonitrile at 60 - 65℃; | 80% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
cyanoacetic acid
citric acid
Conditions | Yield |
---|---|
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; cyanoacetic acid With benzotriazol-1-ol In dichloromethane at 20℃; for 12h; Stage #2: citric acid In acetone at 40℃; for 2h; | 70% |
Stage #1: cyanoacetic acid With pivaloyl chloride; triethylamine In dichloromethane at -15 - 0℃; for 2.5h; Stage #2: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate In dichloromethane at 0℃; for 1h; Stage #3: citric acid In water; acetone at 55 - 65℃; | 67.3% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
1-cyano-cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at -10 - 10℃; | 56.82% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
5-cyclopropylisoxazole-4-carboxylic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 1.5h; Inert atmosphere; Cooling with ice; | 53% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
5-Isopropyl-4-isoxazolecarboxylic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 1.5h; Inert atmosphere; Cooling with ice; | 53% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
N-((tert-butyloxy)carbonyl)iminodiacetic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide at 5 - 30℃; Reagent/catalyst; Temperature; | 43.7% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
2,2'-(4-methoxybenzyl)imino-diacetic acid
Conditions | Yield |
---|---|
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; N-4-methoxyphenylmethyliminodiacetic acid With dmap; dicyclohexyl-carbodiimide at 10 - 35℃; Stage #2: With palladium on activated charcoal; hydrogen at -10℃; under 11251.1 Torr; | 40.8% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide at 5 - 40℃; Temperature; | 35% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
methyl chloroformate
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Schlenk technique; | 34% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
(S)-4-nitrophenyl 3-hydroxypyrrolidine-1-carboxylate
((S)-3-hydroxypyrrolidin-1-yl)((3R,4R)-4-methyl-3-(methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)methanone
Conditions | Yield |
---|---|
With triethylamine In tert-butyl alcohol at 100℃; for 48h; | 33% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
acryloyl chloride
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 1h; | 32% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
N-benzyliminodiacetic acid
Conditions | Yield |
---|---|
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; N-benzyliminodiacetic acid With dmap; dicyclohexyl-carbodiimide at 10 - 30℃; Stage #2: With palladium on activated charcoal; hydrogen under 15001.5 Torr; for 10h; Temperature; | 32% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
5-Ethyl-4-isoxazolecarboxylic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 1.5h; Inert atmosphere; Cooling with ice; | 31% |
3-methyl isoxazole-4-carboxylic acid
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 3h; Inert atmosphere; Cooling with ice; | 23% |
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
acetyl chloride
Conditions | Yield |
---|---|
In pyridine; dichloromethane at 20℃; for 18h; | 15% |
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