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

• 28783-41-7 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride 
• 150322-73-9 1-cyclopropyl-2-(2-fluorophenyl)ethanone 
• 451-82-1 (2-fluorophenyl)acetic acid 
• 204205-33-4 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone 
• 109904-25-8 N-trityl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine 
• 952340-39-5 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate 
• 109904-26-9 5-triphenylmethyl-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine 
• 946402-23-9 2-(2-fluorophenyl)-N-methoxy-N-methylacetamide 
• 1243654-57-0 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-2,4,5,6,7,7a-hexahydrothieno[3,2-c]pyridine hydrobromide 
• 204204-98-8 R-138727 
• 178688-43-2 α-cyclopropylcarbonyl-2-fluorobenzyl chloride 
• 115473-15-9 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride 
• 53885-46-4 5-(2-fluoro-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 446-48-0 o-fluorobenzyl bromide 

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.

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.

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.