Patent ID: 6916924
Filing Date: 2005-07-12
Classification: C07D

Abstract:
1. A process of making a compound of the formula (I): said process comprising: 1) reacting an intermediate compound of the formula (III) with a heteroarylamine compound of the formula (II), said reaction occuring in the presence of a base, in a polar non-protic organic solvent and at a temperature of about 40-100° C. for a reaction time of about 1 to 20 hours, to form an intermediate compound of the formula (Ia):  wherein R 2) coupling the product of step 1), formula (Ia), with electrophile Y—R  wherein:  the heteroaryl ring in formulas (Ia) and (II):  is chosen from:  wherein for the above heteroaryl rings (a), (b) and (d), R Ar is: phenyl, naphthyl, quinoline, isoquinoline, tetrahydronaphthyl, benzofuran, indanyl, indenyl or indole each being optionally substituted with one to three R a bond or a C or L is a cyclic group which is: a) a C b) phenyl, furan, thiophene, pyridine, pyrimidine, pyridinone, dihydropyridinone, maleimide, dihydromaleimide or pyrazine each being optionally independently substituted with 1-3 C wherein said cyclic group is optionally attached to a C Q is selected from the group consisting of: phenyl, naphthyl, pyridine, pyrimidine, pyridazine, furan, thiophene, pyran, naphthyridine and oxazo[4,5-b]pyridine which are optionally substituted with one to three groups selected from the group consisting of halogen, C tetrahydropyran, tetrahydrofuran, 1,3-dioxolanone, 1,3-dioxanone, 1,4-dioxane, N-morpholine, N-thiomorpholine, N-thiomorpholine sulfoxide, N-thiomorpholine sulfone, cyclohexanone, cyclohexanol, pentamethylene sulfide, pentamethylene sulfoxide, pentamethylene sulfone, tetramethylene sulfide, tetramethylene sulfoxide and tetramethylene sulfone which are optionally substituted with one to three groups selected from the group consisting of C C R C C C cyano; and, methoxycarbonyl, ethoxycarbonyl and propoxycarbonyl; R a C R a phenyl, naphthyl or heteroaryl group selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, furyl, tetrahydrofuryl, isoxazolyl, isothiazolyl, quinolinyl, isoquinolinyl, indolyl, benzofuranyl, benzoxazolyl, benzisoxazolyl, benzothiofuranyl, cinnolinyl, pterindinyl, phthalazinyl, naphthypyridinyl, quinoxalinyl, quinazolinyl, purinyl and indazolyl wherein such phenyl, naphthyl or heteroaryl group is optionally substituted with one to five groups selected from the group consisting of a C a fused aryl selected from the group consisting of benzocyclobutanyl, indanyl, indenyl, dihydronaphthyl, tetrahydronaphthyl, benzocycloheptanyl and benzocycloheptenyl, or a fused heterocyclyl selected from cyclopentenopyridine, cyclohexanopyridine, cyclopentanopyrimidine, cyclohexanopyrimidine, cyclopentanopyrazine, cyclohexanopyrazine, cyclopentanopyridazine, cyclohexanopyridazine, cyclopentanoquinoline, cyclohexanoquinoline, cyclopentanoisoquinoline, cyclohexanoisoquinoline, cyclopentanoindole, cyclohexanoindole, cyclopentanobenzoxazole, cyclohexanobenzoxazole, cyclopentanothiophene and cyclohexanothiophene; wherein the fused aryl or fused heterocyclyl ring is substituted with 0 to 3 groups independently selected from phenyl, naphthyl, heterocyclyl selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, thienyl, furyl, isoxazolyl, and isothiazolyl, C R each R N-morpholine and piperazine; R each m is independently 0, 1 or 2; X is O or S.