Patent ID: 6897318

Claim:
A process for making a substituted pyrazole, a tautomer of the substituted pyrazole, or a salt of the substituted pyrazole or tautomer, wherein: the substituted pyrazole corresponds in structure to Formula (I): and the process comprises: forming a mixture by a process comprising introducing a hydrazone and an optionally-substituted benzoyl halide into a reactor, and heating the mixture to a temperature of greater than 50° C.; and the hydrazone corresponds in structure to Formula (II): and the optionally-substituted benzoyl halide corresponds in structure to Formula (III): and R B is halogen; and R 3A , R 3B , and R 3C are independently selected from the group consisting of hydrogen, halogen, hydroxy, cyano, amino, alkyl, aminoalkyl, monoalkylamino, dialkylamino, alkoxy, and alkoxyalkyl, wherein: any carbon of the alkyl, aminoalkyl, monoalkylamino, dialkylamino, alkoxy, or alkoxyalkyl optionally is substituted with one or more substituents independently selected from the group consisting of halogen, hydroxy, and cyano; and one of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 is ═C(R 4 )—; and one of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 is ═N—; and three of Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 are independently selected from the group consisting of ═C(H)— and ═N—; and R 4 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, thiol, carboxy, nitro, alkyl, carboxyalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, carbocyclyl, carbocyclylalkyl, carbocyclylalkenyl, carbocyclyloxy, carbocyclylalkoxy, carbocyclyloxyalkyl, carbocyclylthio, carbocyclylsulfinyl, carbocyclylsulfonyl, heterocyclylthio, heterocyclylsulfinyl, heterocyclylsulfonyl, carbocyclylalkoxy, carbocyclylheterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclylalkoxy, amino, aminoalkyl, alkylamino, alkenylamino, alkynylamino, carbocyclylamino, heterocyclylamino, aminocarbonyl, alkoxy, alkoxyalkyl, alkenyloxyalkyl, alkoxyalkylamino, alkylaminoalkoxy, alkoxycarbonyl, carbocyclyloxycarbonyl, heterocyclyloxycarbonyl, alkoxycarbonylamino, alkoxycarbocyclylamino, alkoxycarbocyclylalkylamino, aminosulfinyl, aminosulfonyl, alkylsulfonylamino, alkoxyalkoxy, aminoalkoxy, aminoalkylaxnino, alkylaminoalkylamino, carbocyclylalkylamino, alkylaminoalkylaminoalkylamino, alkylheterocyclylamino, heterocyclylalkylamino, alkylheterocyclylalkylamino, carbocyclylalkylheterocyclylamino, heterocyclylheterocyclylalkylamino, alkoxycarbonylheterocyclylamino, alkylaminocarbonyl, alkylcarbonylamino, hydrazinyl, alkyihydrazinyl, and carbocyclylhydrazinyl, wherein: any substitutable member of such group optionally is substituted with one or more substituents independently selected from the group consisting of alkyl, alkenyl, hydroxy, halogen, haloalkyl, alkoxy, haloalkoxy, keto, amino, nitro, cyano, alkylsulfonyl, alkylsulfinyl, alkylthio, alkoxyalkyl, carbocyclyloxy, heterocyclyl, and heterocyclylalkoxy.