Amflutizole

Amflutizole

Systematic (IUPAC) name
4-amino-3-[3-(trifluoromethyl)phenyl]-1,2-thiazole-5-carboxylic acid
Clinical data
Identifiers
CAS Registry Number	82114-19-0 Y
ATC code	None
PubChem	CID 192344
ChemSpider	49508 Y
UNII	83N680M457 Y
KEGG	D02896 Y
ChEMBL	CHEMBL2106558
Chemical data
Formula	C11H7F3N2O2S
Molecular mass	288.2 g/mol
SMILES FC(F)(F)c1cccc(c1)c2nsc(c2N)C(=O)O
InChI InChI=1S/C11H7F3N2O2S/c12-11(13,14)6-3-1-2-5(4-6)8-7(15)9(10(17)18)19-16-8/h1-4H,15H2,(H,17,18)  Y Key:KVMCEGAWQYTFKC-UHFFFAOYSA-N  Y
Y (what is this?)  (verify)

Amflutizole is a xanthine oxidase inhibitor used for the treatment of gout.

Synthesis

The tosyl oxime of the meta-trifluromethyl benzoic acid acid cyanide is the reactamt. This is cross reacted with ethyl 2-mercaptoacetate in the presence of a base; displacement of the tosylate by mercaptide leads to the formation of the heterocyclic N–S bond. This intermediate compound is then converted to the carbanion by a second equivalent of base. This adds to the cyano group; protonation then goes on to form the imine, tautomerization of which gives the corresponding amino form. Finally, saponification of the ester thus affords amflutizole as the product.^[1]

References