Patent ID: 6750338
Filing Date: 2004-06-15
Classification: C07D

Abstract:
A process for making a compound or a salt thereof, wherein:the compound corresponds in structure to a formula selected from the group consisting of the following: R1 is selected from the group consisting of hydrogen, alkyl, alkoxy, cycloalkyloxy, cycloalkyl, cycloalkenyl, 5- or 6-member heterocyclyl, and phenyl, wherein: the heterocyclyl is substituted with one or more substituents independently selected from the group consisting of alkyl, halo, hydroxy, alkoxy, cyano, trifluoromethyl, and trifluoromethoxy, and the phenyl is optionally substituted with one or more substituents independently selected from the group consisting of halo, alkoxy, alkylthio, cyano, trifluoromethyl, trifluoromethoxy, alkyl, methylsulfonyl, aminosulfonyl, alkylcarbonylaminosulfonyl, alkenyl, and alkynyl; and R2 is selected from the group consisting of pyridyl, pyrimidyl, triazinyl, hydrogen, halo, alkyl, 6-member heterocyclyl, and phenyl, wherein: the heterocyclyl and phenyl are optionally substituted with up to 2 substituents independently selected from the group consisting of halo, alkoxy, alkylthio, cyano, trifluoromethyl, trifluoromethoxy, alkyl, alkylamino, and dialkylamino; and each R3 is independently selected from the group consisting of hydrogen, alkyl, and phenyl, wherein: the alkyl and phenyl optionally are substituted with one or more substituents independently selected from the group consisting of methylsulfonyl, halo, alkyl, alkoxy, alkylthio, cyano, trifluoromethyl, trifluoromethoxy, and aminosulfonyl; and R6 is selected from the group consisting of the following: â€ƒthe process comprises: reacting an organometallic reagent of the formula R2CH2M with an activated form of a carboxylic acid to produce a ketone corresponding in structure to Formula IIIc: â€ƒtreating the ketone of Formula IIIc with a mixture of carbon disulfide and dihalomethane in the presence of a base and a solvent to produce a dithietane derivative corresponding in structure to Formula IIId: â€ƒreacting the dithietane derivative of Formula IIId with R3NHNH2 to produce a heterocycle corresponding in structure to a formula selected from the group consisting of the following: â€ƒreacting the heterocycle of formula IIIe or IIIf with an activated form of R6 in the presence of a base and a solvent; and M is selected from the group consisting of Li, Na, K, and Mg.