Patent ID: 8835639

Claim:
A process for the preparation of a compound of Formula 1, comprising coupling a carboxylic acid of Formula 2 with an aniline of Formula 3 in the presence of a coupling agent selected from the group consisting of 2-chloro-1,3-dimethyl-2-imidazolium tetrafluoroborate, HBTU, HCTU, 2-chloro-4,6-dimethoxy-1,3,5-triazine, HATU, HOBT/EDC, and propane phosphonic anhydride; wherein each R 2 and R 4 is independently selected from hydrogen, CN, CF 3 , halo, C 1-6 straight or branched alkyl, 3-12 membered cycloaliphatic, phenyl, C 5-10 heteroaryl or C 3-7 heterocyclic, wherein said heteroaryl or heterocyclic has up to 3 heteroatoms selected from O, S, or N, and each C 1-6 straight or branched alkyl, 3-12 membered cycloaliphatic, phenyl, C 5-10 heteroaryl or C 3-7 heterocyclic is independently and optionally substituted with up to three substituents selected from —OR′, —CF 3 , —OCF 3 , SR′, S(O)R′, SO 2 R′, —SCF 3 , halo, CN, —COOR′, —COR′—, —O(CH 2 ) 2 N(R′)(R′), —O(CH 2 )N(R′)(R′), —CON(R′)(R′), —(CH 2 ) 2 OR′, —(CH 2 )OR′, CH 2 CN, optionally substituted phenyl or phenoxy, —N(R′)(R′), —NR′C(O)OR′, —NR′C(O)R′, —(CH 2 ) 2 N(R′)(R′), or —(CH 2 )N(R′)(R′); R 5 is —OC(O)OR′, —OC(O)NHR′, —OC(O)N(R′) 2 , wherein R′ is not hydrogen, or R 4 and R 5 are taken together form the moiety, each X is independently a bond or is an optionally substituted C 1-6 alkylidene chain wherein up to two methylene units of X are optionally and independently replaced by —CO—, —CS—, —COCO—, —CONR′—, —CONR′NR′—, —CO 2 —, —OCO—, —NR′CO 2 —, —O—, —NR′CONR′—, —OCONR′—, —NR′NR′, —NR′NR′CO—, —NR′CO—, —S—, —SO, —SO 2 —, —NR′—, —SO 2 NR′—, NR′SO 2 —, or —NR′SO 2 NR′—; each R x is independently R′, halo, NO 2 , CN, CF 3 , or OCF 3 ; y is an integer from 0-4; and each R′ is independently selected from hydrogen or an optionally substituted group selected from a C 1-8 aliphatic group, a 3-8-membered saturated, partially unsaturated, or fully unsaturated monocyclic ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an 8-12 membered saturated, partially unsaturated, or fully unsaturated bicyclic ring system having 0-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur; or two occurrences of R′ are taken together with the atom(s) to which they are bound to form an optionally substituted 3-12 membered saturated, partially unsaturated, or fully unsaturated monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from N, O, or S.