PROCESSES FOR PRODUCING CYCLOALKYLCARBOXAMIDO-PYRIDINE BENZOIC ACIDS

1 - 70 . (canceled)

71 . A process for preparing a compound of formula 7a:

wherein,

A is a fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl ring;

R 1 is independently selected from —R J , —OR J , —N(R J ) 2 , —NO 2 , halogen, —CN, —C 1-4 haloalkyl, —C 1-4 haloalkoxy, —C(O)N(R J ) 2 , —NR J C(O)R J , —SOR J , —SO 2 R J , —SO 2 N(R J ) 2 , —NR J SO 2 R J , —COR J , —CO 2 R J , —NR J SO 2 N(R J ) 2 , —COCOR 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 halide or OH;

comprising the steps of

ic) reducing Compound 10a in a fourth organic solvent:

wherein,

A is a fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl ring;

R 1 is independently selected from —R J , —OR J , —N(R J ) 2 , —NO 2 , halogen, —CN, —C 1-4 haloalkyl, —C 1-4 haloalkoxy, —C(O)N(R J ) 2 , —NR J C(O)R J , —SOR J , —SO 2 R J , —SO 2 N(R J ) 2 , —NR J SO 2 R J , —COR J , —CO 2 R J , —NR J SO 2 N(R J ) 2 , —COCOR J ;

R J is hydrogen or C 1-6 aliphatic;

R K is C 1-6 aliphatic; and

m is an integer from 0 to 3 inclusive,

with a reducing agent to produce Compound 11a:

wherein, ring A, R 1 , and m are as defined in Compound 10a above;

iic) reacting Compound 11a with a first halogenating agent in a fifth organic solvent to produce Compound 12a:

wherein, ring A, R 1 , and m are as defined in Compound 10a above, and Hal is a halide;

iiic) reacting Compound 12a with a cyanide to produce Compound 13a:

wherein, ring A, R 1 , and m are as defined in Compound 10a above;

ivc) reacting Compound 13a with a compound of formula 13aa in the presence of a third base:

wherein,

Hal is a halide; and

q is an integer from 0 to 3 inclusive; to produce a compound of formula 14a:

wherein,

r is an integer from 1 to 4 inclusive; and

ring A, R 1 , and m are as defined in Compound 10a above;

vc) sequentially reacting Compound 14a with a hydroxide base and second acid to form Compound 15a, which is compound 7a when X═OH:

wherein, r, ring A, R 1 , and m are as defined in Compound 14a above; and

vc) reacting Compound 15a with a second halogenating agent in a sixth organic solvent to form Compound 16a, which is compound 7a when X=halide:

wherein,

Hal is halide; and

r, ring A, R 1 , and m are as defined in Compound 14a above.

72 . The process of claim 71 , wherein the fourth organic solvent is an aprotic solvent.

73 . The process of claim 71 , wherein the fourth organic solvent is toluene.

74 . The process of claim 71 , wherein the reducing agent is a hydride.

75 . The process of claim 71 , wherein the reducing agent is sodium bis(2-methoxyethoxy)aluminum hydride.

76 . The process of claim 71 , wherein the reducing reaction is run at between 15° C. and 40° C.

77 . The process of claim 71 , wherein the fifth organic solvent is an aprotic solvent.

78 . The process of claim 71 , wherein the fifth organic solvent is methyl t-butyl ether.

79 . The process of claim 71 , wherein the first halogenating agent is thionyl chloride.

80 . The process of claim 71 , wherein the reaction of Compound 11a with a first halogenating reaction is run at between 15° C. and 30° C.

81 . The process of claim 71 , wherein the cyanide is sodium cyanide.

82 . The process of claim 71 , wherein the reaction of Compound 12a with a cyanide is run at between 30° C. and 40° C.

83 . The process of claim 71 , wherein the third base is an inorganic base.

84 . The process of claim 71 , wherein the third base is potassium hydroxide.

85 . The process of claim 71 , wherein Compound 13aa is 1-bromo-2-chloroethane.

86 . The process of claim 71 , wherein the reaction of Compound 13a with a compound of formula 13aa is run at between 50° C. and 90° C.

87 . The process of claim 71 , wherein the hydroxide base is sodium hydroxide.

88 . The process of claim 71 , wherein the second acid is an inorganic acid.

89 . The process of claim 71 , wherein the second acid is hydrochloric acid.

90 . The process of claim 71 , wherein the sequential reaction of Compound 14a with a hydroxide base and second acid is run at between 70° C. and 90° C.

91 . The process of claim 71 , wherein the sixth organic solvent is an aprotic solvent.

92 . The process of claim 71 , wherein the sixth organic solvent is toluene.

93 . The process of claim 71 , wherein the second halogenating agent is thionyl chloride.

94 . The process of claim 71 , wherein the reaction of Compound 15a with a second halogenating agent is run at between 40° C. and 80° C.

95 . (canceled)

96 . (canceled)

97 . The process of claim 71 , wherein R K is methyl.

98 - 106 . (canceled)