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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inquiryProduct Description Product website: http://www.finerchem.com Product Name 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indo
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inquiry5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate CAS No.:239463-85-5 Name: 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile
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inquiryItems Standard Result Appearance Off-white to light yellow-green powder Light yellow-green powder Solubility
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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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inquiryShanghai Seasonsgreen Chemical is a high-tech research and development, production, sale and custom synthesis set in one high-tech chemical products enterprises. Our sales and marketing division is located in Shanghai, serving international pharmaceu
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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
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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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inquiryOur 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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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&
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inquiryAppearance:Almost white powder or yellow powder Storage:R.T Package:25kg/Barrel Application:Silodosin Intermediate Transportation:Express/Sea/Air Port:Any port in China
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inquiryAdvantages: Hubei XinRunde Chemical Co., Ltd is a renowned pharmaceutical manufacturer. We can offer high quality products at competitive price in quick delivery with 100% custom pass guaranteed. Never stop striving to offer our best service is
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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 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indo
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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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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 Appearance:light yellow green powder/ Refer to COA Storage
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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
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inquiryBeluga chemical professional supply 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate CAS 239463-85-5 Why choose Beluga chemical 1. Beluga Chemical has a professional RESEARCH a
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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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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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inquiryBest quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia
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inquiryTriumph has the complete production of G- KG - MT service chain,we can make the new technology into productivity quickly in the research and development of new products. Main Service 1.Own made fine chemical products 2.Out sourcing and qua
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inquiryOur advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We have s
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inquiryStock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai
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inquiryOur company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-
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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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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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inquiryProduct Name: 5-[(2R)-2-Aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indole-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate Synonyms: 5-[(2R…Appearance:Solid powder Storage:Sealed,light and oxygen resistant Package:aluminum foil bag,carton
Cas:239463-85-5
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Type:Other
inquiryL-Tartaric acid
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Stage #1: C38H39N3O4 With palladium on activated charcoal; hydrogen Stage #2: L-Tartaric acid Inert atmosphere; | 33.3% |
L-Tartaric acid
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Stage #1: C42H41N3O4 With palladium on activated charcoal; hydrogen Stage #2: L-Tartaric acid Inert atmosphere; | 30.9% |
L-Tartaric acid
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Stage #1: 3-(5-(2-((tert-butoxycarbonyl)amino)propyl)-7-cyanoindolin-1-yl)propylbenzoate With hydrogenchloride In chloroform; water at 25 - 30℃; for 5h; Stage #2: L-Tartaric acid In water; acetone at 20 - 25℃; for 12h; | 23.5% |
L-Tartaric acid
5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 20 - 65℃; Product distribution / selectivity; | |
In water; acetone at 20℃; for 49h; | 2.05 g |
1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; zinc / water; methanol / 20 h / 60 - 65 °C 2: water; tetrahydrofuran / 20 - 65 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 2: water; acetone / 49 h / 20 °C View Scheme |
1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C 2.1: trichlorophosphate / 0 - 50 °C 2.2: Cooling with ice 3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 3.2: 2 h / 80 °C 4.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 5.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0 - 50 °C 1.2: Cooling with ice 2.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 2.2: 2 h / 80 °C 3.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 4.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 1.2: 2 h / 80 °C 2.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 3.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 2: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
L-Tartaric acid
5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
In water; acetone at 25 - 65℃; Resolution of racemate; | A n/a B n/a |
benzoic acid
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: triethylamine / N,N-dimethyl-formamide / 20 °C 1.2: 3 h / 100 °C 2.1: trichlorophosphate / 2 h / 20 °C 2.2: Cooling with ice 3.1: ammonium acetate / 20 - 100 °C 4.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C 5.1: trichlorophosphate / 0 - 50 °C 5.2: Cooling with ice 6.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 6.2: 2 h / 80 °C 7.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 8.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
1-indoline
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: triethylamine / N,N-dimethyl-formamide / 20 °C 1.2: 3 h / 100 °C 2.1: trichlorophosphate / 2 h / 20 °C 2.2: Cooling with ice 3.1: ammonium acetate / 20 - 100 °C 4.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C 5.1: trichlorophosphate / 0 - 50 °C 5.2: Cooling with ice 6.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 6.2: 2 h / 80 °C 7.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 8.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
1-(3-benzoyloxypropyl)-2,3-dihydroindole hydrochloride
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: trichlorophosphate / 2 h / 20 °C 1.2: Cooling with ice 2.1: ammonium acetate / 20 - 100 °C 3.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C 4.1: trichlorophosphate / 0 - 50 °C 4.2: Cooling with ice 5.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 5.2: 2 h / 80 °C 6.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 7.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
1-(3-benzoyloxypropyl)-5-formyl-2,3-dihydroindole
A
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: ammonium acetate / 20 - 100 °C 2.1: sodium tetrahydroborate; potassium hydroxide / tetrahydrofuran; water / -10 - 20 °C 3.1: trichlorophosphate / 0 - 50 °C 3.2: Cooling with ice 4.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 2 h / 50 °C 4.2: 2 h / 80 °C 5.1: platinum on carbon; hydrogen / ethyl acetate / 25 - 30 °C / 6000.6 - 7500.75 Torr / Autoclave 6.1: acetone; water / 25 - 65 °C / Resolution of racemate View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C 2: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 3: water; acetone / 49 h / 20 °C View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: triethylamine / dichloromethane / 8 h / 0 - 25 °C / Inert atmosphere 2.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 0 °C / Inert atmosphere 2.2: 2 h / 0 - 80 °C / Inert atmosphere 3.1: ammonium acetate; acetic acid / 4 h / 80 °C 4.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C 5.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere 5.2: 2 h / 0 - 80 °C / Inert atmosphere 6.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C 7.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C 8.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 9.1: water; acetone / 49 h / 20 °C View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 80 °C / Inert atmosphere 2.1: ammonium acetate; acetic acid / 4 h / 80 °C 3.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C 4.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere 4.2: 2 h / 0 - 80 °C / Inert atmosphere 5.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C 6.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C 7.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 8.1: water; acetone / 49 h / 20 °C View Scheme |
1-(3-benzoyloxypropyl)-5-formyl-2,3-dihydroindole
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: ammonium acetate; acetic acid / 4 h / 80 °C 2.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C 3.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere 3.2: 2 h / 0 - 80 °C / Inert atmosphere 4.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C 5.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C 6.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 7.1: water; acetone / 49 h / 20 °C View Scheme |
1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C 2.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere 2.2: 2 h / 0 - 80 °C / Inert atmosphere 3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C 4.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C 5.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 6.1: water; acetone / 49 h / 20 °C View Scheme |
1-indoline
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: potassium carbonate / acetonitrile / 12 h / 90 °C 2.1: triethylamine / dichloromethane / 8 h / 0 - 25 °C / Inert atmosphere 3.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 0 °C / Inert atmosphere 3.2: 2 h / 0 - 80 °C / Inert atmosphere 4.1: ammonium acetate; acetic acid / 4 h / 80 °C 5.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C 6.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere 6.2: 2 h / 0 - 80 °C / Inert atmosphere 7.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C 8.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C 9.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 10.1: water; acetone / 49 h / 20 °C View Scheme |
1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 80 °C / Inert atmosphere 2.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C 3.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C 4.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 5.1: water; acetone / 49 h / 20 °C View Scheme |
1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C 2: acetic anhydride / tetrahydrofuran / 24 h / 70 °C 3: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C 4: water; acetone / 49 h / 20 °C View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere 1.2: 3.5 h / 50 °C 2.1: hydrogenchloride / water / 12 h / Inert atmosphere; Reflux 3.1: water; methanol / 0.5 h / Inert atmosphere; Reflux View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 12 h / Inert atmosphere; Reflux 2: water; methanol / 0.5 h / Inert atmosphere; Reflux View Scheme |
5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile
L-Tartaric acid
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
In methanol; water for 0.5h; Inert atmosphere; Reflux; |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: trifluoroacetic acid; triethylsilane / toluene / 18 h / 45 °C / Inert atmosphere 2.1: trichlorophosphate / 0.5 h / Cooling with ice; Inert atmosphere 2.2: 3 h / 50 °C 3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere 3.2: 3.5 h / 50 °C 4.1: hydrogenchloride / water / 10 h / Inert atmosphere; Reflux 5.1: water; methanol / 0.5 h / Inert atmosphere; Reflux View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.5 h / Cooling with ice; Inert atmosphere 1.2: 3 h / 50 °C 2.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere 2.2: 3.5 h / 50 °C 3.1: hydrogenchloride / water / 10 h / Inert atmosphere; Reflux 4.1: water; methanol / 0.5 h / Inert atmosphere; Reflux View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere 1.2: 3.5 h / 50 °C 2.1: hydrogenchloride / water / 10 h / Inert atmosphere; Reflux 3.1: water; methanol / 0.5 h / Inert atmosphere; Reflux View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 10 h / Inert atmosphere; Reflux 2: water; methanol / 0.5 h / Inert atmosphere; Reflux View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: trifluoroacetic acid; triethylsilane / toluene / 22 h / 45 °C / Inert atmosphere 2.1: trichlorophosphate / 0.5 h / Cooling with ice; Inert atmosphere 2.2: 3 h / 50 °C 3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere 3.2: 3.5 h / 50 °C 4.1: hydrogenchloride / water / 12 h / Inert atmosphere; Reflux 5.1: water; methanol / 0.5 h / Inert atmosphere; Reflux View Scheme |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
(R)-5-(2-aminopropyl)-1-(3-hydroxypropyl)indoline-7-carbonitrile
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 2h; Reflux; | 100% |
With water; potassium hydroxide In methanol at 20℃; |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile
Conditions | Yield |
---|---|
With sodium carbonate In water; ethyl acetate for 2h; Large scale; | 99% |
With sodium hydroxide In dichloromethane; water at 10℃; pH=11; | 97.5% |
With sodium carbonate In water pH=10; | 1.25 g |
With potassium carbonate In water pH=10; |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In water; ethyl acetate at 20℃; for 1h; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With tetrabutylammomium bromide; sodium carbonate In acetonitrile at 75 - 85℃; for 30h; Reagent/catalyst; Solvent; | 85% |
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In water; ethyl acetate at 20℃; for 1h; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With sodium carbonate In isopropyl alcohol at 80℃; Product distribution / selectivity; | |
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide at 80℃; for 10h; | |
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide In N,N-dimethyl acetamide; acetonitrile at 80℃; for 10h; | |
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In water; ethyl acetate for 2h; Reflux; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With sodium carbonate In toluene Reflux; |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
di-tert-butyl dicarbonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 2h; | 84.48% |
With potassium carbonate In dichloromethane; water at 15 - 25℃; for 5h; | 457 g |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
oxalic acid
1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
Conditions | Yield |
---|---|
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide In N,N-dimethyl acetamide; acetonitrile at 80℃; for 10h; Stage #3: oxalic acid at 50℃; for 0.5h; Solvent; | 82% |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
succinic acid
1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
Conditions | Yield |
---|---|
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide In N,N-dimethyl acetamide; acetonitrile at 80℃; for 10h; Stage #3: succinic acid at 50℃; for 0.5h; | 81% |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
(2E)-but-2-enedioic acid
1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
Conditions | Yield |
---|---|
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In N,N-dimethyl acetamide; acetonitrile at 80℃; for 0.5h; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With potassium iodide In N,N-dimethyl acetamide; acetonitrile at 80℃; for 10h; Stage #3: (2E)-but-2-enedioic acid at 50℃; for 0.5h; | 81% |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
L-Tartaric acid
1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
Conditions | Yield |
---|---|
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt; 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With sodium carbonate In acetonitrile for 24h; Reflux; Stage #2: L-Tartaric acid In ethanol at 20℃; for 5h; | 79.3% |
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In acetic acid butyl ester; water at 45℃; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene In acetic acid butyl ester; water for 18h; Reflux; Stage #3: L-Tartaric acid In acetic acid butyl ester at 80℃; | 4.6 g |
5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt
1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene
A
2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt With potassium carbonate In water; ethyl acetate at 20℃; for 2h; Stage #2: 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene With sodium carbonate In tert-butyl alcohol for 24h; Heating / reflux; |
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