(+/-)-CLOPIDOGREL HYDROCHLORIDE

Base Information

• Chemical Name: (+/-)-CLOPIDOGREL HYDROCHLORIDE
• CAS No.: 90055-48-4
• Deprecated CAS: 120202-73-5,94188-84-8
• Molecular Formula: C16H16ClNO2S
• Molecular Weight: 321.828
• UNII: MX75HY8K68
• DSSTox Substance ID: DTXSID70861221
• Nikkaji Number: J22.957A
• Wikidata: Q27181214
• ChEMBL ID: CHEMBL1333662
• Mol file: 90055-48-4.mol

Synonyms:2-(2-Chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acidmethyl ester;Methyl 2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)-2-(2-chlorophenyl)acetate;94188-84-8;

Chemical Property of (+/-)-CLOPIDOGREL HYDROCHLORIDE

Chemical Property:

• Vapor Pressure: 1.57E-08mmHg at 25°C
• Boiling Point: 423.7 °C at 760 mmHg
• PKA: 4.56±0.20(Predicted)
• Flash Point: 210 °C
• PSA: 68.78000
• Density: 1.317g/cm³
• LogP: 4.32540
• Storage Temp.: Desiccate at +4°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 321.0590276
• Heavy Atom Count: 21
• Complexity: 381

Purity/Quality:

98%,99%, ^*data from raw suppliers

(±)-Clopidogrel (hydrochloride) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3
• Recent EU Clinical Trials: Genotype-gUIded cLopidogrel monoTherapY (POPular GUILTY)

Technology Process of (+/-)-CLOPIDOGREL HYDROCHLORIDE

There total 49 articles about (+/-)-CLOPIDOGREL HYDROCHLORIDE 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: 96.0%

(S)-(+)-clopidogrel (113665-84-2,94188-84-8) + methyl (R)-2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)acetate (120202-69-9,94188-84-8) → clopidogrel (90055-48-4,94188-84-8)

Guidance literature:

With potassium carbonate; In methanol; for 3h; Product distribution / selectivity; Heating / reflux;

Reference yield: 95.7%

methyl (R)-2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)acetate (120202-69-9,94188-84-8) → clopidogrel (90055-48-4,94188-84-8)

Guidance literature:

With potassium hydroxide; potassium carbonate; In dichloromethane; for 6h; Heating;

DOI:10.1080/00304940309355363

Reference yield: 93.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-(2-thiophen-2-yl ethylamino)(2-chlorophenyl)acetic acid methyl ester (141109-26-4) → clopidogrel (90055-48-4,94188-84-8)

Guidance literature:

With hydrogenchloride; In water; at 80 ℃; for 2h;

upstream raw materials:

methyl (R)-2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)acetate

thieno[3,2-c]pyridine hydrochloride

methyl 2-bromo-2-(2-chlorophenyl)acetate

clopidogrel bisulfate

Downstream raw materials:

2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetic acid

clopidogrel bisulfate

(S)-(+)-clopidogrel bisulfate

methyl α-(4,5,6,7-tetrahydrothieno[2,3-c]pyrid-5-yl)-2-chlorophenylacetate benzenesulfonate

Refernces

• 1、 -. "Synthetic method of racemic clopidogrel". Paragraph 0031; 0035; 0040-0043; 0046. . Retrieved 2020/09/12.
• 2、 Arredondo, Vanessa,Hiew, Stanley C.,Gutman, Eugene S.,Premachandra, Ilandari Dewage Udara Anulal,Van Vranken, David L.. "Enantioselective Palladium-Catalyzed Carbene Insertion into the N?H Bonds of Aromatic Heterocycles". supporting information. p. 4156 - 4159. Retrieved 2017/04/03.