Clopidogrel

Common name: Clopidogrel bisulfate, Clopidogrel hydrogensulfate, DV-7314, SR-25990C

Trademarks: Plavix

Molecular Formula: C₁₆H₁₆ClNO₂S. H₂O₄S

CAS Registry Number: 120202-66-6, 113665-84-2 (free base), 94188-84-8 (racemic;free base)

Molecular Weight: 419.9042

CAS Name: (+)-(S)-2-(2-Chlorophenyl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)acetic acid methyl ester hydrogensulfate

Activity: Antiplatelet Therapy, Atherosclerosis Therapy, CARDIOVASCULAR DRUGS, Cerebrovascular Diseases, Treatment of, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, NEUROLOGIC DRUGS, Stroke, Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, P2Y12 (P2T) Antagonists
Intermediates:dl-(2-Chlorophenyl)glycine (141196-64-7)
dl-2-Chloromandelic Acid (10421-85-9)

Clopidogrel synthesis: Drug of Future, 1993, 18(2), 107

Clopidogrel synthesis: WO2002059128A2

(S)-Clopidogrel synthesis: US48747265

Clopidogrel synthesis: Org Process Res Dev 2007, 11(3), 487-489

Clopidogrel synthesis: J Am Chem Soc, 2013, 135(43), 16074–16077 (one step, starting material commercially available)

References:

1. Lohray, V.B.; et. al. Process for preparing clopidogrel. WO2002059128A2
2. Descamps, M.; et. al. Process for the preparation of an N-phenylacetic derivative of tetrahydrothieno(3,2-c)pyridine and its intermediate of synthesis. EP0446569
3. Savi, P.; et. al. Clopidogrel Hydrogensulfate. Drugs Fut 1993, 18(2), 107
4. Wang, L.; et. al. Synthetic Improvements in the Preparation of Clopidogrel. Org Process Res Dev 2007, 11(3), 487-489.
5. MacMillan, D. W. C.; et. al. A Simple Catalytic Mechanism for the Direct Coupling of a-Carbonyls with Functionalized Amines: A One-Step Synthesis of Plavix. J Am Chem Soc 2013, 135(43), 16074-16077.

For more drugs and their synthesis: Synayurajan database