90055-48-4

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

• 944046-20-2 C₁₀H₁₁ClO₅S 
• 28783-41-7 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 54903-50-3 4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 34966-49-9 methyl 2-chlorobenzoylformate 
• 57486-68-7 methyl (2-chlorophenyl)acetate 
• 50615-18-4 5,6,7,8-tetrahydro-4H-thieno[3,2-c]azepine 
• 264882-00-0 methyl 2-(2-chlorophenyl)-2-diazoacetate 
• 156276-21-0 rac-methyl 2-chloromandelate 
• 10421-85-9 2-chloromandelic acid 
• 90055-47-3 methyl 2-chloro-2-(2-chlorophenyl)acetate 
• 122853-32-1 C₁₃H₁₂ClNS 
• 69061-17-2 N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine 
• 30433-91-1 [2-(2-thyenyl)ethyl]amine 

Downstream Products

• 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 academic research and scientific papers

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.

Synthetic method of racemic clopidogrel

The invention relates to a synthesis method of racemic clopidogrel, which comprises the following steps: 1) uniformly mixing methyl benzoylformate, N-chlorosuccinimide, palladium acetate, a ligand andtrifluoroacetic acid, and carrying out ortho-chlorinati

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.

A five coordination Cu(II) cluster-based MOF and its application in the synthesis of pharmaceuticals: Via sp3 C-H/N-H oxidative coupling

Herein, a copper metal-organic framework, termed as VNU-18, containing penta-coordinated sites was successfully synthesized and fully characterized. This material was demonstrated to be an efficient heterogeneous catalyst for the oxidative C-H activation via N-H bonds. The optimized conditions are applicable for the synthesis of pharmaceuticals constructed by α-amino carbonyl skeletons.

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.

Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers

A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Concise Synthesis of (±)-Clopidogrel via Carboxylation of Benzylamine with CO2

A concise and efficient synthesis of (±)-clopidogrel, an antithrombotic agent, is achieved by inserting CO2 at the benzylic position as the key reaction without using any toxic transition metals. The overall yield of the synthetic process is 38% and the salient features include operationally simple process chemistry and fewer steps.

Prodrugs of anti-platelet agents

The invention relates to the compounds of formula I, formula II, formula Ia, formula IIb or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, formula II, formula Ia, formula IIb and methods for treating or preventing atherothrombosis may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment or management of ischemia, stroke, cerebral thrombosis, arterial thrombosis, thrombotic cerebrovascular, cardiovascular diseases and blood clots.

Simple catalytic mechanism for the direct coupling of α-carbonyls with functionalized amines: A one-step synthesis of plavix

The direct α-amination of ketones, esters, and aldehydes has been accomplished via copper catalysis. In the presence of catalytic copper(II) bromide, a diverse range of carbonyl and amine substrates undergo fragment coupling to produce synthetically useful α-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated α-bromo carbonyl species; nucleophilic displacement of the bromide by the amine then delivers the α-amino carbonyl adduct while the catalyst is reconstituted. The practical value of this transformation is highlighted through one-step syntheses of two high-profile pharmaceutical agents, Plavix and amfepramone.