150322-38-6

Basic information

• Product Name: 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one
• Synonyms: -2-oxoethyl);5-(2-Cyclopropyl-1-(2-fluorophenyl);-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H);5-(2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-;5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one;3,5-[cyclopropylcarbonyl-2-flurobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]-pyridine;Prasugrel Thiolactone (Mixture of Diastereomers);5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5,6,7,7a -tetrah
• CAS NO: 150322-38-6
• Molecular Formula: C₁₈H₁₈FNO₂S
• Molecular Weight: 331.4
• Mol File: 150322-38-6.mol

Chemical Properties

• Boiling Point: 483.619 °C at 760 mmHg
• Flash Point: 246.284 °C
• Appearance: /
• Density: 1.357 g/cm³
• Vapor Pressure: 1.65E-09mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.02±0.20(Predicted)
• CAS DataBase Reference: 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one(150322-38-6)
• EPA Substance Registry System: 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one(150322-38-6)

Safety Data

• Hazardous Substances Data: 150322-38-6(Hazardous Substances Data)

Usage

Uses

An inactive metabolite of Prasugrel (P701150).

InChI:InChI=1/C18H18FNO2S/c19-14-4-2-1-3-13(14)17(18(22)11-5-6-11)20-8-7-15-12(10-20)9-16(21)23-15/h1-4,9,11,15,17H,5-8,10H2

Upstream product

• 204205-33-4 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone 
• 115473-15-9 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride 
• 226386-47-6 2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 949922-62-7 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylic acid tert-butyl ester 
• 1333429-05-2 2-(4-morpholinyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 1333429-06-3 2-(N-morpholinyl)-5-(alpha-cyclopropylcarbonyl-2-fluorobenzyl)-4.5.6.7-tetrahydro-thieno-[3,2-c]pyridine 
• 150322-43-3 prasugel 
• 204204-98-8 R-138727 
• 178688-43-2 α-cyclopropylcarbonyl-2-fluorobenzyl chloride 
• 53885-46-4 5-(2-fluoro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 446-48-0 o-fluorobenzyl bromide 
• 952340-38-4 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 326-62-5 2-fluorophenyl acetonitrile 
• 345-35-7 2-fluorobenzyl chloride 

Downstream Products

• 150322-43-3 prasugel 
• 204204-98-8 R-138727 
• 1234572-10-1 R-133490 
• 1243654-57-0 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide 
• 150322-39-7 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydro thieno[3,2-c] pyridine hydrochloride 
• 1618107-96-2 5-(5-chloro-1-(2-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate hydrochloride 
• 1056459-37-0 2-acetoxy-5-[5-chloro-1-(2-fluorophenyl)-2-oxopentyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 1234572-11-2 C₁₈H₂₀FNO₄S 
• 204204-73-9 R-138727 
• 1007595-75-6 C₁₈H₂₀FNO₃S 

Relevant articles and documents

Process improvements of prasugrel hydrochloride: An adenosine diphosphate receptor antagonist

An improved process for the synthesis of prasugrel hydrochloride with an overall yield of 58%, 99.9% purity, and meeting all other quality requirements is described.

A "bunch" method for preparing method for prasugrel

The present invention relates to a method for preparing prasugrel through a one-pot-porridge method. According to the method, in the presence of an alkali, 5,6,7,7a-tetrahydrothieno[3,2-c]pyridine-2(4H)-one hydrochloride and cyclopropyl-2-bromo-2-(2-fluorophenyl)ethyl ketone react and then continuously react with acetic anhydride without an intermediate treatment, and finally the target compound prasugrel is collected from the reaction products. The technical scheme of the present invention has the following characteristics that: the hydroxyl protection is not required, the use of DMF, toluene and other strongly-toxic and high-boiling point solvents is avoided, the process is safe and easy to control, the steps are simplified, the post-treatment is simple, the purity and the yield of the product is maintained or improved, the cost is reduced, and the large-scale production is easily achieved.

Synthesis of a novel series of amino acid prodrugs based on thienopyridine scaffolds and evaluation of their antiplatelet activity

The thienopyridines class of drugs used as P2Y12 receptor antagonists plays a vital role in antiplatelet therapy. To further optimized this compound class, we designed and synthesized a series of amino acid prodrugs of 2-hydroxytetrahydrothienopyridine. All compounds were then evaluated for their inhibitory effect on ADP-induced platelet aggregation in rats and then ED50 and bleeding time of the most potent compounds were compared with commercial drugs. The results showed compound 5c could be a potent and safe candidate for further research.

A high-purity prasugrel preparation method

A high-purity prasugrel preparation method, compared with the prior art, the invention adopts the new preparation process, by acylation and esterification, condensation, dehydrohalogenation, hydrolysis, cyclization and acetylation can be for preparing high-purity prasugrel, mild conditions, yield is higher; at the same time 1 - alkenyl - [six hydrogen pyrazoles - 1 - (α - cyclopropyl carbonyl - 2 - fluorobenzyl) - 2 - yl] - acetic acid R ester alkali is added to the catalyst so that the hydrolysis reaction can be carried through to the end, further improves the reaction yield, in addition to the 2 - acetoxy - 5 - (α - cyclopropyl carbonyl - 2 - fluorobenzyl) - 4, 5, 6, 7 - tetrahydro-thieno [3, 2 - c] pyridine has further purification, to obtain a high purity prasugrel, and the unexpected technical effects.

Intermediate for synthetizing prasugrel, preparation method of intermediate, and method for synthetizing prasugrel

The present invention discloses an intermediate for synthetizing prasugrel, a preparation method of the intermediate, and a method for synthetizing prasugrel by using the intermediate. In the invention, cyclopropyl-2-fluorobenzyl ketone reacts with different chlorine source compounds under the action of an oxidizing agent to obtain the intermediate, and the intermediate is subjected to condensation with 2-Oxo-2,4, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridine-2(4H)-one hydrochloride and then is subjected to acetylation to obtain prasugrel; and the synthetizing route is simple, the cost is low, and operation is convenient.

PROCESS FOR THE PREPARATION OF HIGH-PURITY PRASUGREL

The field of invention relates to a novel process, suitable for industrial scale manufacture, for the preparation of high-purity 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7- tetrahydrothieno[3,2-c]pyridine-2-yl acetate, prasugrel, of Formula (I). Especially in large-scale production, one of the main causes of piling up the impurities is the use of ether solvents consequently in each step in this procedure ethers are excluded. Avoiding the ethers resulted new conditions for production of intermediates in the different steps of our procedure. Conditions were determined so that each step from the beginning contributes to minimizing the impurity content of the end-product.

AN IMPROVED PROCESS FOR THE PREPARATION OF PRASUGREL INTERMEDIATES

The present invention relates to an improved method for preparing 2-oxo prasugrel, 5-(andalpha;-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2,-c]pyridine (chemical formula 1), which is a major intermediate of prasugrel. More specifically, the present invention provides an improved method which is characterized by adding water as a catalyst and dividedly feeding an inorganic basic composition when 2-oxo prasugrel is synthesized through a condensation reaction between andalpha;-cyclopropylcarbonyl-2-fluorobenzylbromide represented by chemical formula 2 and 2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2,-c]pyridine hydrochloride represented by chemical formula 3.COPYRIGHT KIPO 2017

A Simple and Efficient Method for the Preparation of α-Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant

α-Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α-halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three-step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram-scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments. (Figure presented.).

An anti-platelet drug prasugrel method for the preparation of (by machine translation)

The invention discloses an anti-platelet drug prasugrel method for preparing, the method includes: 1) the 1 [...] cyclopropyl -2 the [...] (the 2 [...] phenyl) - 2 the and iodine monobromide[...] ethanone and the 1 [...] butyl -3 the imidazolium methyl bromination[...] contact is obtained by reacting the 1 [...] cyclopropyl -2 the- [...] the 2 [...] (the 2 [...] phenyl) - 2 the [...] ethanone; 2) and in iodine under the presence of alkali, the step 1) product with the 2 [...] oxo -2, 4, 5, 6, 7 the [...] the 7a [...] tetrahydro-thieno [3,2 the ??c] pyridine hydrochloride is obtained by reacting the 5 [...] (α-cyclopropane carbonyl -2 the [...] fluorobenzyl) - 2 the [...] oxo -2, 4, 5, 6, 7, 7a-tetrahydro-thieno [3,2 the ??c] pyridine; 3) steps 2) product with triethylamine mixed, then instillment second grade anhydride, shall prasugrel stirring reaction. The method of preparing the prasugrel of this invention high yield, is easy to be treated, is suitable for industrial production. (by machine translation)

Method for preparing prasugrel intermediate

The invention discloses a method for preparing a prasugrel intermediate 5-(alpha-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-1,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine. The method comprises a following reaction route. As a result of experiments, the method provided by the invention has the advantages of simple operation, mild reaction conditions, low requirement on equipment, inexpensive and easy-to-obtain raw materials, high yield, and low production cost. An adopted solvent can synchronously recovered. The method can be easily applied in large-scale productions. The method meets the requirements of prasugrel industrialized production, and has industrial application value.