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
• Article Data: 28

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 
• 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 
• 150322-43-3 prasugel 
• 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 
• 30433-91-1 [2-(2-thyenyl)ethyl]amine 
• 1333429-04-1 2-(4-morpholinyl)-N-tert-butyloxycarbonyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 1333429-07-4 1-cyclopropyl-2-(2-fluoro-phenyl)-2-{2-[(2-hydroxy-ethyl)-methyl-amino]-6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl}-ethanone 
• 1333429-08-5 2-[methyl-(4,5,6,7-tetrahydro-thieno[3.2-c]pyridin-2-yl)-amino]-ethanol 

Downstream Products

• 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 
• 150322-43-3 prasugel 
• 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.

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.

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.