Sematilide

Sematilide
	source ↗
Names
	Preferred IUPAC name N-[2-(Diethylamino)ethyl]-4-(methanesulfonamido)benzamide
Identifiers
CAS Number	101526-83-4 Y; 101526-62-9 (HCl) Y;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL95804 Y;
ChemSpider	52715 Y;
MeSH	Sematilide
PubChem CID	58505;
UNII	0NHB13IN3R Y; 1B8MC21ZI2 (HCl) Y;
CompTox Dashboard (EPA)	DTXSID0058720 ;
	InChI InChI=1S/C14H23N3O3S/c1-4-17(5-2)11-10-15-14(18)12-6-8-13(9-7-12)16-21(3,19)20/h6-9,16H,4-5,10-11H2,1-3H3,(H,15,18) Y Key: KHYPYQZQJSBPIX-UHFFFAOYSA-N Y; InChI=1/C14H23N3O3S/c1-4-17(5-2)11-10-15-14(18)12-6-8-13(9-7-12)16-21(3,19)20/h6-9,16H,4-5,10-11H2,1-3H3,(H,15,18) Key: KHYPYQZQJSBPIX-UHFFFAOYAU;
	SMILES O=S(=O)(Nc1ccc(cc1)C(=O)NCCN(CC)CC)C;
Properties
Chemical formula	C14H23N3O3S
Molar mass	313.42 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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).¹² 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.; Morgan, Thomas K.; Reiser, H. J. (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.)

[1] Lumma, William C.; Wohl, Ronald A.; Davey, David D.; Argentieri, Thomas M.; Devita, Robert J.; Gomez, Robert P.; Jain, Vijay K.; Marisca, Anthony J.; Morgan, Thomas K.; Reiser, H. J. (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.

[2] David D. Davey, William C. Lumma, Jr., Ronald A. Wohl, U.S. patent 4,544,654 (1985 to Schering A.G.)

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