Chemistry:Sematilide
From HandWiki
Sematilide is an antiarrhythmic agent. It is the same structure as for procainamide, differing only by the placement of a mesyl sulfonamide moiety to the anilino nitrogen.
Synthesis
Sematilide can be synthesized from benzocaine (1).[1][2] Reaction with mesyl chloride, followed by saponification and removal of the water from the reaction mixture, gives sodium 4-[(methylsulfonyl)amino]benzoate (2). Chlorination with thionyl chloride gives 4-[(methylsulfonyl)amino]benzoyl chloride. Amide formation with N,N-diethylethylenediamine (3) then concludes the synthesis of sematilide (4).
References
- ↑ Lumma, William C.; Wohl, Ronald A.; Davey, David D.; Argentieri, Thomas M.; Devita, Robert J.; Gomez, Robert P.; Jain, Vijay K.; Marisca, Anthony J. et al. (1987). "Rational design of 4-[(methylsulfonyl)amino]benzamides as class III antiarrhythmic agents". Journal of Medicinal Chemistry 30 (5): 755–758. doi:10.1021/jm00388a001. PMID 3572962.
- ↑ David D. Davey, William C. Lumma, Jr., Ronald A. Wohl, U.S. Patent 4,544,654 (1985 to Schering A.G.)
 |  |
