Patent ID: 8530651

Claim:
A method for making a compound of Formula (IX): wherein: R 1 and R 2 are both methyl or together form a cyclopropyl group; R 3 and R 4 are hydrogen; V, W, X, and Y, are independently chosen from the group consisting of H, F, Cl, I, Br, CN, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy and C 1-6 alkanoyl; and R 5 is H, C 1-6 alkyl or OH; comprising the steps: (a) nitrating a compound of formula (X): to form a compound of formula (XI): (b) reacting the compound of formula (XI) under reducing conditions to form a compound of formula (XII): (c) reacting the compound of formula (XII) with an alkyl- or aryl-sulfonyl halide of formula R 6 SO 2 T and an organic base to form a compound of formula (XIII): wherein: R 6 is an optionally substituted C 1-6 alkyl group or an optionally substituted aryl group, each of which can be optionally substituted where chemically possible by 1 to 3 substituents independently selected from the group consisting of C 1-6 alkyl, C 1-6 haloalkyl, —SR 8 , —OR 9 , —NR 8 R 9 , —NO 2 , SCF 3 , halogen, —C(O)R 8 , —CN, and —CF 3 , where R 8 and R 9 are independently H or C 1-6 alkyl; and T is halo; (d) reacting the compound of formula (XIII) with an organic base and a glycine derivative of formula (XIV) wherein R 7 is an optionally substituted C 1-6 alkyl group or aryl group, each of which can be optionally substituted by 1 to 3 substituents independently selected from the group consisting of C 1-6 alkyl, C 1-6 haloalkyl, —SR 8 , —OR 9 , —NR 8 R 9 , —NO 2 , SCF 3 , halogen, —C(O)R 8 , —CN, and —CF 3 , where R 8 and R 9 are independently H or C 1-6 alkyl; to form a compound of formula (XV): (e) reacting the compound of formula (XV) under reducing conditions to form a compound of formula (XVI): (f) reacting the compound of formula (XVI) under bromocyanation conditions to form a compound of formula (XVII): (g) reacting the compound of formula (XVII) under cycloalkylation conditions to form the compound of formula (IX):