Benzamide compounds

A process for preparing a compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:

• comprising reacting an acid of Formula A having the structure:
• or a pharmaceutically acceptable salt thereof, with a sulfonamide of Formula B having the structure:
• to provide the compound of Formula (I), or a pharmaceutically acceptable salt thereof:
• wherein:
• R1 is selected from the group consisting of hydrogen, halogen, a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 haloalkyl, a substituted or unsubstituted C3-C6 cycloalkyl, a substituted or unsubstituted C1-C6 alkoxy, an unsubstituted mono-C1-C6 alkylamine and an unsubstituted di-C1-C6 alkylamine;
• each R2 is independently selected from the group consisting of halogen, a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 haloalkyl and a substituted or unsubstituted C3-C6 cycloalkyl;
• or
• when m is 2 or 3, each R2 is independently selected from the group consisting of halogen, a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 haloalkyl and a substituted or unsubstituted C3-C6 cycloalkyl, or two R2 groups taken together with the atom(s) to which they are attached form a substituted or unsubstituted C3-C6 cycloalkyl or a substituted or unsubstituted 3 to 6 membered heterocyclyl;
• R3 is selected from the group consisting of X—R3A,
• R3A is a substituted or unsubstituted 5 to 10 membered heteroaryl;
• R4 is selected from the group consisting of NO2, S(O)R6, SO2R6, halogen, cyano and an unsubstituted C1-C6 haloalkyl;
• R5 is —X1-(Alk1)n-R7;
• Alk1 is selected from an unsubstituted C1-C4 alkylene and a C1-C4 alkylene substituted with 1, 2 or 3 substituents independently selected from fluoro, chloro, an unsubstituted C1-C3 alkyl and an unsubstituted C1-C3 haloalkyl;
• R6 is selected from the group consisting of a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 haloalkyl and a substituted or unsubstituted C3-C6 cycloalkyl;
• R7 is selected from a substituted or unsubstituted C1-C6 alkoxy, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted 3 to 10 membered heterocyclyl, hydroxy, amino, a substituted or unsubstituted mono-substituted amine group, a substituted or unsubstituted di-substituted amine group, a substituted or unsubstituted N-carbamyl, a substituted or unsubstituted C-amido and a substituted or unsubstituted N-amido;
• m is 0, 1, 2 or 3;
• n is selected from 0 and 1;
• X1 is —NH—;
• and
• X is selected from the group consisting of —O—, —S— and —NH—.

A compound selected from the group consisting of:

• methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4,4-dimethyl-2-(3-methylbicyclo[1.1.1]pentan-1-yl)cyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoate,
• methyl 2-((1H-pyrrolo[2,3-b]pyridine-5-yl)oxy)-4-(4-((2-(3-ethylbicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoate,
• methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((2-(3-(difluoromethyl)bicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoate, and
• methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-dimethyl-2-(3-trifluoromethylbicyclo[1.1.1]pentan-1-yl)cyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoate,
• or a pharmaceutically acceptable salt of any of the foregoing.