144077-07-6

Basic information

• Product Name: Clopidogrel hydrogen sulfate
• Synonyms: Clopidogrel bisulphate; clopidogrel hydrogen sulphate; clopidogrel sulphate; clopidogrel bisulfate; methyl (+)-(s)-a-(2-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4h)acetate, hydrogen sulfate salt; (2S)-(2-chlorophenyl)(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethanoic acid sulfate (1:1); (+/-)-Clopidogrel bisulfate; Clopidogerl Bisulfate; Clopidogrel bisulphate Ⅰ/Ⅱ; Clopidogrel Bisulfate II; Clopidogrel Bisulfate I; Clopidogrel Bisulfate, FormI/FormII; Clopidogrel sulfate; Clopidogrel Hydrogensulfate
• CAS NO: 144077-07-6
• Molecular Formula: C₁₅H₁₈ClNO₆S₂
• Molecular Weight: 419.8950
• Mol File: 144077-07-6.mol
• Article Data: 86

Chemical Properties

• Melting Point: 184℃
• Boiling Point: 447.3°C at 760 mmHg
• Flash Point: 224.3°C
• Vapor Pressure: 8.71E-09mmHg at 25°C
• CAS DataBase Reference: Clopidogrel hydrogen sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: Clopidogrel hydrogen sulfate(144077-07-6)
• EPA Substance Registry System: Clopidogrel hydrogen sulfate(144077-07-6)

Safety Data

• Safety Statements: S22-24/25:
• Hazardous Substances Data: 144077-07-6(Hazardous Substances Data)

Upstream product

• 113665-84-2 (S)-(+)-clopidogrel 
• 90055-48-4 clopidogrel 
• 120202-71-3 clopidogrel hydrogen sulfate 
• 120202-69-9 methyl (R)-2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)acetate 
• 1233025-55-2 (S)-clopidogrel hydrogen sulfate 
• 141109-18-4 (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride 
• 50-00-0 formaldehyd 
• 7664-93-9 sulfuric acid 
• 909279-85-2 clopidogrel camphorsulfonate 
• 40412-06-4 2-(2-thienyl)ethyl tosylate 
• 141109-14-0 methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate 
• 54903-50-3 4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 1198409-05-0 (1R)-1-methyl-2-oxo-2-tetrahydro-1H-pyrrolylethyl 2-bromo-2-(2-chlorophenyl)acetate 
• 1198409-07-2 (1R)-1-methyl-2-oxo-2-tetrahydro-1H-pyrrolylethyl (2S)-α-5-(4,5,6,7-tetrahydro[3,2-c]thienopyridyl)-2-chlorophenylacetate 

Downstream Products

• 1326217-43-9 (S)-methyl 2-(2-bromo-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)acetate 
• 90055-48-4 clopidogrel 
• 1373492-22-8 5-(2-chloro-1-(2-chlorophenyl)ethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 1373492-23-9 2-((2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)ethyl)malonic acid diethyl ester 
• 1373491-72-5 4-(2-chlorophenyl)-4-(6,7-dihydro-4H-thieno[3,2-c]pyridine-5-yl)butyric acid ethyl ester 
• 1373491-51-0 4-(2-chlorophenyl)-4-(6,7-dihydro-4H-thieno[3,2-c]pyridine-5-yl)butan-1-ol 

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.

Preparation method of clopidogrel hydrogen sulfate intermediate

The present invention relates to a preparation method of a clopidogrel hydrogen sulfate intermediate. (+)-2-chlorophenylglycine methyl ester and alpha-thiopheneethanol p-toluenesulfonate are adopted as raw materials, a reaction solvent and an acid-binding agent are added for a condensation reaction, the condensation reaction process is divided into a first stage and a second stage, and when 60-95% of the condensation reaction is completed, first-stage reaction is completed; after the first-stage reaction is completed, firstly part of the reaction solvent is removed, and then second-stage reaction is carried out; and after the second-stage reaction is completed, a target product is obtained, namely the clopidogrel hydrogen sulfate intermediate. After the first-stage reaction is completed, part of the reaction solvent is removed firstly, and then the second-stage reaction is continued, so that the concentration of the reaction material can be increased in the later stage of the condensation reaction, the use amount of the reaction solvent is reduced, and racemization and side reaction in the reaction process are effectively inhibited, thereby improving the chiral purity of the product, increasing the yield, reducing the use of auxiliary materials greatly, and reducing the production cost.

Synthetic hydrosulfuric acid clopidogrel and intermediate of the new method (by machine translation)

The invention relates to a synthesis of the clopidogrel hydrogen sulfate of the new method, through 2 - thiophene ethylamine and N - benzyl - 2 - (2 - chlorophenyl) - 2 - carbonyl acetamide generate condensation reaction, generating imine; imine asymmetric hydrogenation reaction is reduced to the corresponding secondary amine. Under acidic conditions, secondary amine with formaldehyde generating ring, get the clopidogrel free base, then acidified by sulfuric acid, to obtain the clopidogrel hydrogen sulfate. The present invention provides a synthetic route of the short, relates to the reaction are classical organic chemical reaction, mild reaction conditions, the operation is simple, with high enantio-selectivity, high yield, high turn over number of characteristics, the vast majority of the substrate in the thousandths of a dosage of the catalyst obtained in the circumstances of 99% or more of the conversion and 97% -99% ee value of, to achieve the highest transformed number 100000, has extremely high industrial application value. (by machine translation)