Highly productive and scalable approach to synthesize ticlopidine: A potent thienopyridine anti-platelet aggregation drug

Abstract

Ticlopidine (trade name Ticlid), an acidic thienopyridine derivative, is an effective, well-known and long-acting inhibitor of platelet aggregation. Because of its potent inhibitory activity for treating a variety of diseases, the development of efficient approaches for accessing ticlopidine represents an important endeavour. Therefore, in this research work, we developed a promising novel five-step synthetic approach for synthesizing ticlopidine. This method provides ticlopidine in 60% overall yield from readily available starting material viz. thiophene. In this methodology, all steps afforded excellent yields and are operationally simple and environmentally acceptable. This approach also offers various attractive advantages, for example, it's applicable for large-scale synthesis, has simple work-up procedures and short reaction times, and uses inexpensive and readily available reagents. Furthermore, 4,5,6,7-tetrahydrothieno[3,2-c]pyridine is a key precursor for the synthesis of numerous bioactive compounds such as prasugrel and clopidogrel. This protocol provides 4,5,6,7-tetrahydrothieno[3,2-c]pyridine in 62% overall yield via a 4-step synthetic approach.

Keywords

• Organic chemistry
• Pharmaceutical chemistry
• Biochemistry
• Ticlopidine
• Ticlid
• Anti-platelet