Process for making 2-oxindole-1-carboxamides

C - Chemistry – Metallurgy – 07 – D

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260/207.7

C07D 209/34 (2006.01) C07D 209/38 (2006.01) C07D 209/56 (2006.01) C07D 407/06 (2006.01) C07D 409/06 (2006.01) C07D 491/04 (2006.01)

Patent

CA 1253490

64680-316D ABSTRACT The invention relates to a process for making a compound of the formula Image wherein X is selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having 1 to 4 carbons, cycloalkyl hav- ing 3 to 7 carbons, alkoxy having 1 to 4 carbons, alkylthio having 1 to 4 carbons, trifluoromethyl, alkylsulfinyl having 1 to 4 carbons, alkylsulfonyl having 1 to 4 carbons, nitro, phenyl, alkanoyl having 2 to 4 carbons, benzoyl, thenoyl, alkanamido hav- ing 2 to 4 carbons, benzamido and N,N-dialkylsulfamoyl having 1 to 3 carbons in each of said alkyls; and Y is selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having 1 to 4 carbons, cycloalkyl having 3 to 7 carbons, alkoxy having 1 to 4 carbons, alkylthio having 1 to 4 carbons and trifluoromethyl; or X and Y when taken together are a 4,5-, 5,6- or 6,7- methylenedioxy group or a 4,5-, 5,6- or 6,7- ethylenedioxy group; or X and Y when taken together and when attached to adjacent carbon atoms, form a divalent radical Z, wherein Z is selected from the group consisting of Image 64680-316D Image Image and wherein W is oxygen or sulfur; and R is selected from the group consisting of hydrogen and -CO-R1, wherein R1 is selected from the group consisting of alkyl having 1 to 6 carbons, cycloalkyl having 3 to 7 carbons, cycloalkenyl having 4 to 7 carbons, phenyl, substituted phenyl, phenylalkyl hav- ing 1 to 3 carbons in said alkyl, (substituted phenyl)alkyl having 1 to 3 carbons in said alkyl, phenoxyalkyl having 1 to 3 carbons in said alkyl, (substituted phenoxy)alkyl having 1 to 3 carbons in said alkyl, (thiophenoxy)alkyl having 1 to 3 carbons in said alkyl, naphthyl, bicyclo[2.2.1]heptan-2-yl, bicyclo[2.2.1]hept-5- en-2-yl and -(CH2)n-Q-R°; wherein the substituent on said substituted phenyl, said (substituted phenyl)alkyl and said (substituted phenoxy)alkyl is selected from the group consisting of fluoro, chloro, bromo, alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons and trifluoro- methyl; n is zero, 1 or 2; Q is a divalent radical derived from a compound selected from the group consisting of furan, thiophene, pyrrole, pyrazole, imidazole, thiazole, isothiazole, oxazole, isoxazole, 1,2,3-thiadiazole, 1,3,4-thiadiazole, 1,2,5-thiadiazole, tetrahydrofuran, tetrahydrothiophene, tetrahydropyran, tetrahydro- thiopyran, pyridine, pyrimidine, pyrazine, benzo[b]furan and benzo[b]thiophene; and R° is hydrogen or alkyl having 1 to 3 car- bons; 64680-316D which comprises hydrolyzing under neutral or acid con- ditions a compound of the formula Image wherein X, Y and R are as defined above. The 2-oxindole-1-carbox- amide products include analgesic and anti-inflammatory compounds.

566447

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