methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate sulfate

Base Information

• Chemical Name: methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate sulfate
• CAS No.: 135046-48-9
• Molecular Formula: C16H18ClNO6S2
• Molecular Weight: 419.907
• Hs Code.: 2934999090
• European Community (EC) Number: 603-890-4
• ChEMBL ID: CHEMBL1895693
• DSSTox Substance ID: DTXSID4046024
• Wikidata: Q106210757
• Mol file: 135046-48-9.mol

Synonyms:135046-48-9;(+/-)-Clopidogrel bisulfate;Clopidogrel Sulfate (racemic);methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate sulfate;Clopidogrel hydrogensulfate;DTXSID4046024;(+/-) Clopidogrel hydrogensulfate;135046-48-9 (sulfate);R-(-)-Clopidogrel Hydrogen Sulfate;( inverted exclamation markA)-Clopidogrel (bisulfate);DTXCID601474236;CAS-135046-48-9;NCGC00159321-02;(s)-(+)-clopidogrel bisulfate;MFCD00876395;(S)-(+)-Clopidogrel hydrogen sulfate;Clopidogrelhydrogensulfate;SCHEMBL2307984;CHEMBL1895693;rac-Clopidogrel Hydrogen Sulfate;HMS3654H06;BCP04255;Methyl (S)-(+)-2-(2-Chlorophenyl)-2-[6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl]acetate Sulfate;Tox21_111570;AKOS005146215;Tox21_111570_1;AC-5597;NCGC00095065-01;NCGC00095065-02;NCGC00163329-03;HY-107867;CS-0030751;EN300-296088;F19458;A855057;J-004276;Q-200883;( inverted exclamation markA) Clopidogrel hydrogen sulfate;(+/-) Clopidogrel hydrogensulfate, >=98% (HPLC), powder;methyl2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetatesulfate;(+)-methyl (2-chlorophenyl)-(6,7-dihydro-4h-thieno[3,2-c]pyrid-5-yl)acetate bisulfate salt;(+/-)-methyl (2-chlorophenyl)-(6,7-dihydro-4h-thieno[3,2-c]pyrid-5-yl)acetate hydrogen sulfate salt;(R)-(-)-Methyl 2-(2-Chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate Hydrogen Sulfate;(S)-(+)-Methyl 2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)-2-(2-chlorophenyl)acetate hydrogensulfate;Clopidogrel hydrogen sulfate;(2-Chlorophenyl)-6,7-dihydrothieno[3,2-C]pyridine-5-(4H)-acetic acid methyl ester sulfate;methyl 2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate;sulfuric acid;methyl 2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate

Chemical Property of methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate sulfate

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 8.71E-09mmHg at 25°C
• Melting Point: 184 °C
• Boiling Point: 423.7 °C at 760 mmHg
• Flash Point: 210 °C
• PSA: 140.76000
• LogP: 4.03980
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~26mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 419.0264073
• Heavy Atom Count: 26
• Complexity: 463

Purity/Quality:

99%, ^*data from raw suppliers

rac-Clopidogrel Hydrogen Sulfate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O
• Recent EU Clinical Trials: A pilot study investigating the antiplatelet effect of generic clopidogrel versus Plavix? – is there any difference in platelet reactivity in healthy subjects?
• Uses: Used as an antithrombotic platelet aggregation inhibitors rac-Clopidogrel Hydrogen Sulfate is used in the synthesis of Clopidogrel derivatives as platelet aggregation inhibitors.

Technology Process of methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate sulfate

There total 7 articles about methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate sulfate 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: 91.0%

clopidogrel (90055-48-4,94188-84-8) → clopidogrel bisulfate (135046-48-9,120202-71-3,144077-07-6)

Guidance literature:

With sulfuric acid; In water; acetone; at 20 ℃; for 2h;

Reference yield: 90.0%

6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride (28783-41-7) + methyl 2-bromo-2-(2-chlorophenyl)acetate (85259-19-4,622835-93-2,66504-71-0) → clopidogrel bisulfate (135046-48-9,120202-71-3,144077-07-6)

Guidance literature:

6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride; With sodium carbonate; In water; at 25 ℃; for 0.5h;

methyl 2-bromo-2-(2-chlorophenyl)acetate; In water; toluene; at 20 ℃; for 12h;

With sulfuric acid; In ethyl acetate; for 1h; Reagent/catalyst; Solvent;

DOI:10.1080/15533174.2015.1137028

Reference yield: 85.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + methyl 2-bromo-2-(2-chlorophenyl)acetate (85259-19-4,622835-93-2,66504-71-0) → clopidogrel bisulfate (135046-48-9,120202-71-3,144077-07-6)

Guidance literature:

[2-(2-thyenyl)ethyl]amine; formaldehyd; In 1,2-dichloro-ethane; for 4h; Heating / reflux;

With hydrogenchloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 30 - 70 ℃; for 4h;

methyl 2-bromo-2-(2-chlorophenyl)acetate; With sulfuric acid; sodium carbonate; more than 3 stages; Product distribution / selectivity;

upstream raw materials:

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

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

clopidogrel

formaldehyd

Downstream raw materials:

clopidogrel

5-(2-chloro-1-(2-chlorophenyl)ethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

2-((2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)ethyl)malonic acid diethyl ester

4-(2-chlorophenyl)-4-(6,7-dihydro-4H-thieno[3,2-c]pyridine-5-yl)butyric acid ethyl ester

Refernces

• 1、 -. "RACEMIZATION PROCESS FOR THE PREPARATION OF AN INTERMEDIATE OF CLOPIDOGREL HYDROGEN SULPHATE". Page/Page column 13. . Retrieved 2009/07/18.
• 2、 -. "Preparation of Clopidogrel and Its Analogues Methyl Tetrahydrothienopyridine Acetate Compuunds". Page/Page column 11. . Retrieved 2008/12/08.