178688-43-2

Basic information

• Product Name: 2-Chloro-1-cyclopropyl-2-(2-fluorophenyl)ethanone
• Synonyms: 2-Chloro-1-cyclopropyl-2-(2-fluorophenyl)ethanone;Prasugrel INT;Ethanone, 2-chloro-1-cyclopropyl-2-(2-fluorophenyl)-;2-Chloro-2-(2-fluorophenyl)-1-cyclopropylethanone
• CAS NO: 178688-43-2
• Molecular Formula: C₁₁H₁₀ClFO
• Molecular Weight: 212.65
• Mol File: 178688-43-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 274.058°C at 760 mmHg
• Flash Point: 119.546°C
• Appearance: /
• Density: 1.316
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: 2-Chloro-1-cyclopropyl-2-(2-fluorophenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-1-cyclopropyl-2-(2-fluorophenyl)ethanone(178688-43-2)
• EPA Substance Registry System: 2-Chloro-1-cyclopropyl-2-(2-fluorophenyl)ethanone(178688-43-2)

Safety Data

• Hazardous Substances Data: 178688-43-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to dark yellow liquid

InChI:InChI=1/C11H10ClFO/c12-10(11(14)7-5-6-7)8-3-1-2-4-9(8)13/h1-4,7,10H,5-6H2

Upstream product

• 150322-73-9 1-cyclopropyl-2-(2-fluorophenyl)ethanone 

Downstream Products

• 952340-38-4 2-(tert-butyldimethylsilyloxy)-5-(α-cyclopropylformyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 150322-43-3 prasugel 
• 150322-38-6 5-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one 
• 951380-42-0 5-(α-cyclopropylcarbonyl-2-fluorobenzyl)-2-oxo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 

Relevant articles and documents

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.

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.

PROCESS FOR PRODUCTION OF PRASUGREL HYDROCHLORIDE HAVING HIGH PURITY

An object of the present invention is to provide prasugrel hydrochloride with a reduced content of CATP, and the like. In the formulae, R represents a protecting group for a hydroxyl group. A method for producing prasugrel hydrochloride represented by the above formula is provided, characterized by comprising, in step (i), controlling, at low values, the temperature during the addition, optionally dropwise, of a chlorinating agent and the reaction temperature after the addition, optionally dropwise, of the chlorinating agent.