As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch
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inquiryThe above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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inquiry1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s
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inquiryCangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new ap
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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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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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inquiry(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one Basic information Product Name: (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4
WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et
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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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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 serv
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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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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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inquiry(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one CAS:764667-65-4 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research an
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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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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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inquiryMassive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and
Cas:764667-65-4
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inquiryZibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi
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inquiry(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one CAS NO.764667-65-4Appearance:Powder Storage:Refrigerator Package:according to customers' requirements Application:Medical inte
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inquirySuperior quality, moderate price & quick delivery. Appearance:Brown Oil Storage:Well-sealed and put in dry and cool conditions. Protected from direct sunlight or high temperature. Package:as per your request Application:Sitagliptin interm
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inquiryProduct name: (2Z)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-Dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-Trifluorophenyl)butan-2-one CAS No.: 764667-65-4 Molecule Formula:C16H12F6N4O2 Molecule Weight:406.28 Purity: 99.0% Package: 25kg/drum
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inquiryHuarong Industrial Group Limited established since 2006 , has been actively developing specialty products for Finished Dosages, APIs, Intermediates, and Fine chemicals markets in North America, Europe, Korea, Japan, Mid-East and all over the World.
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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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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
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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,
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inquiryLocated in Hangzhou National Hi-Tech Industrial Development Zone, zhongqichem is a technical company mainly focus on the Custom synthesis, manufacturing, sales of chemicals to various industries. Benefiting from the outstanding customer service and h
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inquiry5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
With 4-methyl-morpholine In ethyl acetate for 6h; Reflux; | 98.1% |
With N-ethyl-N,N-diisopropylamine In Isopropyl acetate at 85℃; for 4h; | 93.3% |
With N-ethyl-N,N-diisopropylamine In Isopropyl acetate at 85℃; for 3.5h; | 92% |
3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide at 41.1℃; Kinetics; Further Variations:; Temperatures; | 91% |
4-(2,4,5-trifluorophenyl)-3-oxobutanoic acid
3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: 4-(2,4,5-trifluorophenyl)-3-oxobutanoic acid With oxalyl dichloride In dichloromethane at 10 - 35℃; Stage #2: 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine With triethylamine In dichloromethane at 0 - 15℃; | 91% |
cycl-isopropylidene malonate
(2,4,5-trifluorophenyl)acetic acid
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 45 - 55℃; Large scale reaction; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With trifluoroacetic acid In acetonitrile at 50 - 55℃; for 6h; Large scale reaction; | 90% |
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20 - 50℃; for 2 - 3h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In N,N-dimethyl acetamide at 40 - 70℃; Stage #3: With sodium hydrogencarbonate In N,N-dimethyl acetamide; water at 20 - 45℃; | 89% |
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 50℃; for 2 - 3h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With trifluoroacetic acid In acetonitrile at 40 - 55℃; for 6h; | |
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 0 - 40℃; for 2 - 3h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In ISOPROPYLAMIDE at 40 - 70℃; | |
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile at 50℃; Stage #2: With pivaloyl chloride In acetonitrile at 50℃; for 3.75h; Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride With trifluoroacetic acid In acetonitrile at 55℃; for 6h; |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
With hydrogenchloride In water; ethyl acetate at 25 - 30℃; | 90% |
With hydrogenchloride In water; ethyl acetate at 25 - 30℃; for 0.5h; | 90% |
2,4,5-trifluorobenzyl bromide
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: 2,4,5-trifluorobenzyl bromide With magnesium In tetrahydrofuran at 35 - 45℃; for 2.16667h; Stage #2: 3-oxo-3-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]propanenitrile In tetrahydrofuran; toluene at 0 - 5℃; for 4h; Temperature; | 89.5% |
(2,4,5-trifluorophenyl)acetic acid
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: (2,4,5-trifluorophenyl)acetic acid With cycl-isopropylidene malonate; N-ethyl-N,N-diisopropylamine; dmap In ISOPROPYLAMIDE at 20 - 40℃; Stage #2: With pivaloyl chloride In ISOPROPYLAMIDE at 0 - 5℃; for 1 - 3h; Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In ISOPROPYLAMIDE at 40 - 70℃; | 89% |
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 0 - 40℃; for 2 - 3h; Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In N,N-dimethyl acetamide at 40 - 70℃; for 1h; |
cycl-isopropylidene malonate
3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine
(2,4,5-trifluorophenyl)acetic acid
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid With dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 50 - 55℃; Stage #2: 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine With trifluoroacetic acid In N,N-dimethyl acetamide at 55℃; for 6h; | 84% |
3-oxo-4-(2,4,5-trifluorophenyl)-butyric acid ethyl ester
3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Reagent/catalyst; Solvent; Temperature; | 82% |
cycl-isopropylidene malonate
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: 2-(2,3,4-trifluorophenyl)acetic acid With 1,1'-carbonyldiimidazole In Isopropyl acetate at 45℃; for 0.166667h; Stage #2: cycl-isopropylidene malonate In Isopropyl acetate at 20 - 40℃; for 25.5h; Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In Isopropyl acetate at 90℃; for 12h; | 71% |
Stage #1: 2-(2,3,4-trifluorophenyl)acetic acid With 1,1'-carbonyldiimidazole In ISOPROPYLAMIDE at 45℃; for 0.166667h; Stage #2: cycl-isopropylidene malonate In ISOPROPYLAMIDE at 20 - 50℃; for 25h; Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In ISOPROPYLAMIDE at 90℃; for 12h; | 69% |
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / toluene / 3 h / 92 - 95 °C 2.1: magnesium / tetrahydrofuran / 2.17 h / 35 - 45 °C 2.2: 4 h / 0 - 5 °C View Scheme |
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: C15H13F3O4; 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In N,N-dimethyl acetamide at 40 - 70℃; for 1h; Stage #2: With sodium hydrogencarbonate In N,N-dimethyl acetamide; water at 20 - 45℃; for 3 - 5h; |
sodium 1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-2-(2,4,5-trifluorophenyl)ethanolate
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
With methanesulfonic acid In acetonitrile at 25 - 85℃; Product distribution / selectivity; |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
With potassium dichromate; sulfuric acid; acetic acid at 25 - 30℃; for 24h; |
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In toluene at 25 - 30℃; Reflux; | |
With N-ethyl-N,N-diisopropylamine In toluene at 25 - 30℃; for 8h; Product distribution / selectivity; Reflux; | |
Stage #1: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride With 4-methyl-morpholine In ethyl acetate at 10℃; for 20h; Stage #2: 5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione In ethyl acetate for 6h; Reflux; | 115 g |
(2,4,5-trifluorophenyl)acetic acid
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: dmap / acetonitrile / 25 - 30 °C 1.2: 30 - 50 °C 2.1: hydrogenchloride / ethyl acetate; water / 0.5 h / 25 - 30 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 4 h / 20 - 25 °C 2.1: dichloromethane / 4 h / -5 - 30 °C / Inert atmosphere 2.2: 0 - 5 °C 3.1: N-ethyl-N,N-diisopropylamine / toluene / 8 h / 25 - 30 °C / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine / ISOPROPYLAMIDE / 2 - 3 h / 0 - 40 °C 2.1: ISOPROPYLAMIDE / 40 - 70 °C 2.2: 20 - 45 °C View Scheme |
2-(2,4,5-trifluorophenyl)acetyl chloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: dichloromethane / 4 h / -5 - 30 °C / Inert atmosphere 1.2: 0 - 5 °C 2.1: N-ethyl-N,N-diisopropylamine / toluene / 8 h / 25 - 30 °C / Reflux View Scheme |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: dmap / acetonitrile / 25 - 30 °C 1.2: 30 - 50 °C 2.1: hydrogenchloride / ethyl acetate; water / 0.5 h / 25 - 30 °C View Scheme |
sitagliptin
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: sitagliptin With sulfuric acid; sodium nitrite Stage #2: With potassium dichromate | |
Stage #1: sitagliptin With sulfuric acid; sodium nitrite Stage #2: With potassium dichromate |
1-bromo-2,4,5-trifluorobenzene
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper(l) iodide; L-valine; potassium phosphate / dimethyl sulfoxide / 24 h / 90 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C View Scheme |
1-t-Butoxycarbonylpiperazine
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 1,4-dioxane / 1 h / 20 °C 1.2: 7 h / 70 °C 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C View Scheme |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 2: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 3: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 4: N,N-dimethyl acetamide / 6 h / 70 °C View Scheme |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 2: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 3: N,N-dimethyl acetamide / 6 h / 70 °C View Scheme |
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide at 70℃; for 6h; |
2,4-dichloro-5-fluorobenzoyl chloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: potassium fluoride; tetraphenylphosphonium bromide; 18-crown-6 ether / 1,2-dichloro-benzene / 15 h / 120 - 130 °C / Inert atmosphere 2: 1,2-dichloro-benzene / 140 °C 3: potassium fluoride / 1,2-dichloro-benzene / 7 h / 110 °C / Inert atmosphere 4: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere 5: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 6: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 7: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 8: N,N-dimethyl acetamide / 6 h / 70 °C View Scheme |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1,2-dichloro-benzene / 140 °C 2: potassium fluoride / 1,2-dichloro-benzene / 7 h / 110 °C / Inert atmosphere 3: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere 4: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 5: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 6: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 7: N,N-dimethyl acetamide / 6 h / 70 °C View Scheme |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: potassium fluoride / 1,2-dichloro-benzene / 7 h / 110 °C / Inert atmosphere 2: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere 3: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 4: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 5: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 6: N,N-dimethyl acetamide / 6 h / 70 °C View Scheme |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sulfuric acid; sodium chloride / water / 8 h / 20 °C / Inert atmosphere 2: hydrogenchloride / water / 5 h / 70 °C / Inert atmosphere 3: phosphonic Acid; iodine; methanesulfonic acid / 24 h / 110 °C 4: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / N,N-dimethyl acetamide / 3 h / 5 - 40 °C / Inert atmosphere 5: N,N-dimethyl acetamide / 6 h / 70 °C View Scheme |
2-(2,4,5-trifluorophenyl)acetonitrile
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 40 - 45 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 10 - 30 °C 3.1: oxalyl dichloride / dichloromethane / 10 - 35 °C 3.2: 0 - 15 °C View Scheme |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / dichloromethane / 10 - 30 °C 2.1: oxalyl dichloride / dichloromethane / 10 - 35 °C 2.2: 0 - 15 °C View Scheme |
(R)-1-phenyl-ethyl-amine
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(R,Z)-3-[(1-phenylethyl)amino]-1-{3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl}-4-(2,4,5-trifluorophenyl)but-2-en-1-one
Conditions | Yield |
---|---|
With acetic acid In toluene at 110℃; Reflux; | 100% |
With acetic acid In isopropyl alcohol at 40℃; | 99.7% |
In acetic acid; isopropyl alcohol at 50℃; for 18h; | 95.2% |
With acetic acid for 5h; Product distribution / selectivity; Reflux; | 92.07% |
(R)-1-phenyl-ethyl-amine
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(3R)-3-[[(1R)-1-phenylethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 5h; Reagent/catalyst; Solvent; stereoselective reaction; | 95% |
(R)-2-methylpropane-2-sulfinamide
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(R)-2-methyl-N-((R)-4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4] triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)propane-2-sulfinamide
Conditions | Yield |
---|---|
With platinum(IV) oxide; hydrogen In tetrahydrofuran at 0℃; under 4500.45 Torr; for 5h; Catalytic behavior; Temperature; Pressure; Solvent; | 93% |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one
Conditions | Yield |
---|---|
With ammonium hydroxide; ammonium acetate In methanol at 58℃; for 0.5h; | 92% |
With ammonium acetate In methanol at 40 - 45℃; Large scale reaction; | 82% |
With ammonia In methanol at 25 - 65℃; | 79.8% |
L-phenylglycine amide
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(2S)-2({(1Z)-3-oxo-1-(2,4,5-trifluorobenzyl)-3-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-]pyrazin-7(8H)-yl]prop-1-enyl}amino-2-phenylethanamide)
Conditions | Yield |
---|---|
With acetic acid In isopropyl alcohol at 45℃; for 10h; | 91.3% |
In acetic acid; isopropyl alcohol at 50℃; for 18h; |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
sitagliptin
Conditions | Yield |
---|---|
Stage #1: 1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione With ammonium formate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-1-[(S)-2-(di-tert-butylphosphino)ferrocenyl]ethyl-di-2-methylphenylphosphine In methanol at 55℃; for 5h; Stage #2: With hydrogen In methanol at 55℃; under 12929 Torr; for 20h; Product distribution / selectivity; | 91% |
Multi-step reaction with 3 steps 1: isopropyl alcohol; acetic acid / 18 h / 50 °C 2: sodium tetrahydroborate; acetic acid / tetrahydrofuran / 3 h / 20 °C 3: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr View Scheme | |
Multi-step reaction with 3 steps 1: isopropyl alcohol; acetic acid / 18 h / 50 °C 2: sodium tetrahydroborate; formic acid / tetrahydrofuran / -30 °C 3: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr View Scheme |
L-phenylglycine amide
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(2S)-2({(1R)-3-oxo-1-(2,4,5-trifluorobenzyl)-3-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-α]pyrazin-7(8H)-yl]propyl}amino)-2-phenylethanamide
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid In acetonitrile at 20℃; for 5h; Reagent/catalyst; stereoselective reaction; | 87% |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
dehydrositagliptin
Conditions | Yield |
---|---|
With ammonium acetate; ammonia In methanol; water at 55℃; for 6h; | 75% |
With ammonium acetate; ammonia In methanol; water at 0 - 45℃; | |
With ammonium acetate |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: 1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione With dimethylsulfide borane complex In methanol at 20℃; for 0.416667h; Stage #2: With methanesulfonyl chloride; triethylamine In tetrahydrofuran at 0 - 40℃; for 20h; Temperature; Reagent/catalyst; Solvent; | 65.5% |
N-methoxylamine hydrochloride
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
3-(methoxyimino)-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one
Conditions | Yield |
---|---|
With pyridine In ethanol at 20℃; for 4h; | 20% |
With pyridine In ethanol at 20℃; for 4h; | 20% |
ammonia
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
dehydrositagliptin
Conditions | Yield |
---|---|
With ammonium acetate In methanol; water at 0 - 45℃; for 0.25 - 0.5h; |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: 1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione With sodium hydroxide In methanol; water at 25 - 30℃; Stage #2: With calcium acetate In methanol; water at 25 - 60℃; |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(R/S)-3-hydroxy-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate; acetic acid at 15℃; for 2h; Product distribution / selectivity; | |
With methanol; sodium tetrahydroborate at 0℃; for 1.5h; |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(R)-3-hydroxy-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
Conditions | Yield |
---|---|
Stage #1: 1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In toluene at 0 - 5℃; for 3h; Inert atmosphere; Stage #2: With methanol In toluene | |
With β-nicotinamide adenine dinucleotide phosphate disodium salt In aq. phosphate buffer; isopropyl alcohol at 37℃; Enzymatic reaction; | n/a |
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
(Z)-3-(hydroxyimino)-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one
Conditions | Yield |
---|---|
With pyridine; hydroxylamine hydrochloride In ethanol at 25 - 30℃; for 2h; |
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