951380-42-0

Basic information

• Product Name: 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2(3H)-one
• Synonyms: 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2(3H)-one;5-[Cyclopropylcarbonyl-2-flurobenzyl)-2-oxo-2, 4, 5, 6, 7, 7a-hexahydrothieno [3, 2-c]-pyridine;5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-2H,3H,4H,5H,6H,7H-thieno[3,2-c]pyridin-2-one;Prasugrel IMpurity 3;Prasugrel Thiolactone Tautomer;Prasugrel Thiolactone TautoMer Discontinued See: P701165;Prasugrel Impurity 10;Prasugrel Impurity 16
• CAS NO: 951380-42-0
• Molecular Formula: C₁₈H₁₈FNO₂S
• Molecular Weight: 331.4
• Product Categories: Aromatics;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 951380-42-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 462.5 °C at 760 mmHg
• Flash Point: 233.5 °C
• Appearance: /
• Density: 1.36
• Refractive Index: 1.64
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2(3H)-one(951380-42-0)
• EPA Substance Registry System: 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2(3H)-one(951380-42-0)

Safety Data

• Hazardous Substances Data: 951380-42-0(Hazardous Substances Data)

Usage

Uses

An intermediate in the synthesis of 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/h1-4,11,17H,5-10H2

Upstream product

• 178688-48-7 C₇H₉NOS 
• 1100905-46-1 3-cyclopropyl-1-(2-fluorophenyl)-3-oxopropyl methanesulfonate 
• 446-48-0 o-fluorobenzyl bromide 
• 178688-43-2 α-cyclopropylcarbonyl-2-fluorobenzyl chloride 
• 178688-49-8 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridin-2-one p-toluenesulfonate 
• 150322-73-9 1-cyclopropyl-2-(2-fluorophenyl)ethanone 
• 204205-33-4 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone 

Downstream Products

• 1190589-94-6 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide 
• 150322-43-3 prasugel 

Relevant articles and documents

METHOD FOR PREPARING PRASUGREL

The present invention relates to a method for synthesizing prasugrel, comprising the following steps: converting o-fluorobenzyl cyclopropyl ketone into α-cyclopropylcarbonyl-2-fluorobenzyl halide (compound 2) using dibromohydantoinhydantoin as halogenation reagent and acetic acid as solvent, then 2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine p-toluenesulfonate (compound 4) is obtained with high yield by a concerted catalysis using a phase transfer catalyst and an inorganic salt, then is condensed and acylated to obtain prasugrel as a gum. The present invention also provides a method for purifying prasugrel comprising crystallizing using alcohols as a crystallization solvent to obtain prasugrel crystals with a high purity.

A METHOD FOR THE MANUFACTURE OF HIGHLY PURE PRASUGREL

The invention deals with preparation of the substance prasugrel, using 3- cyclopropyl-1 -(2-fluorophenyl)-3-oxopropyl methanesulfonate for alkylation of 2-oxo- thienotetrahydropyridine, which may be in the form of a salt, e.g. with hydrochloric acid or p-toluenesulfonic acid. The resulting compound of formula II is acylated, preferably with acetanhydride, preferably directly in the reaction mixture without isolation, and the produced prasugrel of formula I can then be crystallized directly from the reaction mixture.

PROCESS FOR THE PREPARATION OF 2-ACETOXY-5-(α -CYCLOPRPYLCARBONYL -2-FLUOROBENZYL)-4,5,6,7-TETRAHYDROTHIENO[3,2-C]PYRIDINE

The present invention relates to a process for the preparation of 2-Acetoxy-5-(α-cycloprpylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine and pharmaceutically acceptable salt thereof using a 2-acetoxy-tetrahydrothienopyridine derivatives i.e. compound of formula (VI) and (VIII) or salt thereof or acid addition salt of 5-(α-cycloprpylcarbonyl-2-fluorobenzyl)-2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine of formula (II). The present invention also relates to the process for the preparation of 2-acetoxy-tetrahydrothienopyridine derivatives i.e. compound of formula (VI) and (VIII) or salt thereof and acid addition salt of compound of formula (II).