90055-48-4

Basic information

• Product Name: (+/-)-CLOPIDOGREL HYDROCHLORIDE
• Synonyms: (+/-)-CLOPIDOGREL HYDROCHLORIDE;α-(2-Chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetic acid methyl ester;2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester;methyl 2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate;methyl 2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)ethanoate;Methyl2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)-2-(2-chlorophenyl)acetatehydrochloride;S-Clopidogrel hydrochloride
• CAS NO: 90055-48-4
• Molecular Formula: C₁₆H₁₆ClNO₂S
• Molecular Weight: 344.2561
• Mol File: 90055-48-4.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 423.7 °C at 760 mmHg
• Flash Point: 210 °C
• Appearance: /
• Density: 1.317g/cm³
• Vapor Pressure: 1.57E-08mmHg at 25°C
• Storage Temp.: Desiccate at +4°C
• PKA: 4.56±0.20(Predicted)
• CAS DataBase Reference: (+/-)-CLOPIDOGREL HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-CLOPIDOGREL HYDROCHLORIDE(90055-48-4)
• EPA Substance Registry System: (+/-)-CLOPIDOGREL HYDROCHLORIDE(90055-48-4)

Safety Data

• Hazardous Substances Data: 90055-48-4(Hazardous Substances Data)

Usage

Biological Activity

Selective, high affinity P2Y 12 receptor antagonist (pK i = 6.9 for hP2Y 12 receptor). Inhibits ADP-induced platelet aggregation; potent antithrombotic agent.

InChI:InChI=1/C16H16ClNO2S.ClH/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14;/h2-5,7,9,15H,6,8,10H2,1H3;1H

Upstream product

• 77-78-1 dimethyl sulfate 
• 929200-21-5 (+/-)-(2-chlorophenyl)-(4,5,6,7-4H-thieno[3,2,-c]pyrid-5-yl) potassium acetate 
• 929200-19-1 sodium (+/-)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)-acetate 
• 67-56-1 methanol 
• 90055-55-3 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetic acid 
• 1130832-68-6 2-{2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetylamino}-1,1-dimethylethyl methyl carbonate 
• 90055-47-3 methyl 2-chloro-2-(2-chlorophenyl)acetate 
• 28783-41-7 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride 
• 113665-84-2 (S)-(+)-clopidogrel 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 865187-82-2 2-(2-bromoethyl)-3-(bromomethyl)thiophene 
• 141109-14-0 2-(2-chlorophenyl)glycine methyl ester hydrochloride 
• 54903-50-3 4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 1303860-06-1 (+/-)-Methyl (2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetate 
• 113665-84-2 (S)-(+)-clopidogrel 
• 120202-69-9 methyl (R)-2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)acetate 
• 120202-71-3 racemic clopidogrel bisulfate 
• 847986-65-6 (R)-(-)-camphorsulphonic scid salt of methyl (R)-(-)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetate 
• 909279-85-2 clopidogrel camphorsulfonate 
• 1147350-77-3 cis-5-thiol metabolite 
• 144457-28-3 SR 26334 
• 1376615-31-4 (E)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetaldehyde O-methyl oxime 
• 1376615-30-3 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethyl acetate 
• 1376615-29-0 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetaldehyde 

Relevant articles and documents

Copper (II) bromide catalysed one pot bromination and amination for the green, cost-effective synthesis of clopidogrel

Copper (II) bromide catalyzed one pot α-bromination and followed by amination of a benzylic ester is reported. The α-bromination of ester by copper (II) bromide generates copper (I) bromide and HBr. The copper (I) bromide is oxidized to copper (II) bromide by N-Methylmorpholine-N-Oxide (NMO) in presence of HBr. The amines undergo nucleophilic substitution reaction with α-brominated ester compound. This methodology was applied for the synthesis of the familiar antiplatelet drug clopidogrel. This green process is an alternate to classical methods for the synthesis of clopidogrel, which requires, generates stochiometric amount of brominating agents and HBr, respectively.

Electrolysis promoted reductive amination of electron-deficient aldehydes/ketones: a green route to the racemic clopidogrel

An electrocatalytic reductive amination of electron-deficient aldehydes/ketones was developed, which could be used in the synthesis of functionalized tertiary amines and large scale preparation of racemic clopidogrel. A plausible mechanism involving an iminium cation intermediate was proposed.

Enantioselective Palladium-Catalyzed Carbene Insertion into the N?H Bonds of Aromatic Heterocycles

C3-substituted indoles and carbazoles react with α-aryl-α-diazoesters under palladium catalysis to form α-(N-indolyl)-α-arylesters and α-(N-carbazolyl)-α-arylesters. The products result from insertion of a palladium-carbene ligand into the N?H bond of the aromatic N-heterocycles. Enantioselection was achieved using a chiral bis(oxazoline) ligand, in many cases with high enantioselectivity (up to 99 % ee). The method was applied to synthesize the core of a bioactive carbazole derivative in a concise manner.