5-(5-Chloro-1-(2-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate

Base Information

• Chemical Name: 5-(5-Chloro-1-(2-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate
• CAS No.: 1056459-37-0
• Molecular Formula: C20H21ClFNO3S
• Molecular Weight: 409.909
• Hs Code.: 2934999090
• Mol file: 1056459-37-0.mol

Synonyms:5-(5-chloro-1-(2-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate;5-(5-chloro-1-(3-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno [3,2-c]pyridin-2-yl acetate

Chemical Property of 5-(5-Chloro-1-(2-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate

Chemical Property:

• Boiling Point: 522.6±50.0 °C(Predicted)
• PKA: 3.90±0.20(Predicted)
• PSA: 74.85000
• Density: 1.312±0.06 g/cm3(Predicted)
• LogP: 4.43790

Purity/Quality:

99% ^*data from raw suppliers

PRASUGREL CATP IMPURITY 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Prasugrel 5-Chloro-2-pentanone is an impurity of Prasugrel Hydrochloride(P701150). A novel antiplatelet agent; it is a third-generation thienopyridine. Antiplatelet agent Prasugrel showed greater platelet inhibition and decreased incidence of ischemic events than Clopidogrel but may induce increased incidence of bleeding in patient with acute coronary syndrome

Technology Process of 5-(5-Chloro-1-(2-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate

There total 11 articles about 5-(5-Chloro-1-(2-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.4%

C18H19ClFNO2S + acetic anhydride (108-24-7) → 2-acetoxy-5-[5-chloro-1-(2-fluorophenyl)-2-oxopentyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1056459-37-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20 ℃; for 24h; Solvent; Reagent/catalyst;

Reference yield:

5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate (952340-39-5) + 1-bromo-5-chloro-1-(2-fluorophenyl)-pentan-2-one (1373350-58-3) → 2-acetoxy-5-[5-chloro-1-(2-fluorophenyl)-2-oxopentyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1056459-37-0)

Guidance literature:

5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate; 1-bromo-5-chloro-1-(2-fluorophenyl)-pentan-2-one; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 1.5h;

With acetic anhydride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 15 - 20 ℃; for 1h;

Reference yield:

1-cyclopropyl-2-(2-fluorophenyl)ethanone (150322-73-9) → 2-acetoxy-5-[5-chloro-1-(2-fluorophenyl)-2-oxopentyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1056459-37-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / water / 3 h

2.1: toluene-4-sulfonic acid; N-Bromosuccinimide / 0.5 h / 40 °C

3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h

3.2: 1 h / 15 - 20 °C

With hydrogenchloride; N-Bromosuccinimide; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide;

upstream raw materials:

6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride

1-cyclopropyl-2-(2-fluorophenyl)ethanone

N-trityl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-one p-toluenesulfonate

Downstream raw materials:

2-acetoxy-5-[5-chIoro-1-(2-fluorophenyl)pentyl]-4,5,6,7-tetrahydro-4H-thieno[3,2-c] pyridine maleate

5-(5-chloro-1-(2-fluorophenyl)-2-oxopentyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate hydrochloride

Refernces

• 1、 Umasankara Sastry,Nageswrara Rao,Appi Reddy,Gandhi. "Identification and synthesis of impurities formed during prasugrel hydrochloride preparation". . p. 7783 - 7789. Retrieved 2013/09/23.
• 2、 -. "PROCESS FOR PRODUCTION OF PRASUGREL HYDROCHLORIDE HAVING HIGH PURITY". Page/Page column 13. . Retrieved 2009/12/07.