Processes for producing cycloalkylcarboxamido-pyridine benzoic acids

1. A process for preparing a compound of formula 1:

comprising the step of:

ia) reacting a compound of formula 6a:

wherein,

R is H or C 1-6 aliphatic;

R 1 is independently selected from —R J , —OR J , or —CO 2 R J ;

R J is hydrogen or C 1-6 aliphatic;

o is an integer from 0 to 3 inclusive; and

p is an integer from 0 to 5 inclusive;

with a compound of formula 7a:

wherein,

A is a fused heterocycloalkyl;

R 1 is independently selected from —R J or —OR J ;

R J is hydrogen or C 1-6 aliphatic;

m is an integer from 0 to 3 inclusive;

n is an integer from 1 to 4 inclusive; and

X is a halo or OH;

in an organic solvent in the presence of a base.

2. The process of claim 1 , wherein the organic solvent is an aprotic solvent.

3. The process of claim 1 , wherein the organic solvent is toluene.

4. The process of claim 1 , wherein the base is an organic base.

5. The process of claim 1 , wherein the base is triethylamine.

6. The process of claim 1 , wherein the reaction between compound 6a and compound 7a is carried out in the presence of a catalytic amine.

7. The process of claim 1 , wherein the reaction between compound 6a and compound 7a is carried out in the presence of a catalytic amount of dimethylaminopyridine.

8. The process of claim 1 , wherein when R 1 on the phenyl ring in formula 1 is an ester, the process further comprises de-esterifying the compound of formula 1 in a biphasic mixture comprising water, an organic solvent, and an acid to give an acid salt.

9. The process of claim 8 , wherein the organic solvent is acetonitrile.

10. The process of claim 8 , wherein the acid is an inorganic acid.

11. The process of claim 8 , wherein the acid is hydrochloric acid.

12. The process of claim 8 , wherein the de-esterification reaction is run at between 20° C. and 60° C.