Heteroaryl sulfonamides and CCR2/CCR9

A method of preparing a compound of Formula A, comprising:

• (a) reacting a compound of Formula B with a Grignard reagent to produce a compound of Formula C;
• and
• (b) deprotecting the compound of Formula C to produce the compound of Formula A,
• wherein
• Ar is selected from the group consisting of substituted or unsubstituted C6-10 aryl and substituted or unsubstituted 5- to 10-membered heteroaryl;
• Y6 is halogen or substituted or unsubstituted C1-8 alkyl;
• R is a protecting group;
• R100 is selected from the group consisting of hydrogen, substituted or unsubstituted C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl and substituted or unsubstituted 3- to 10-membered heterocycle;
• and
• R67 is independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-8 alkyl, substituted or unsubstituted C2-8 alkenyl, substituted or unsubstituted C2-8 alkynyl, —CN, ═O, —NO2, —OR68, —OC(O)R68, —CO2R68, —C(O)R68, —C(O)NR69R68, —OC(O)NR69R68, —NR70C(O)R68, —NR70C(O)NR69R68, —NR69R68, —NR70CO2R68, —SR68, —S(O)R68, —S(O)2R68, —S(O)2NR69R68, —NR70S(O)2R68, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted 5- to 10-membered heteroaryl and substituted or unsubstituted 3- to 10-membered heterocyclyl;
• R68, R69, and R70 are independently selected from the group consisting of hydrogen, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, aryl, and heteroaryl;
• or
• R69 and R68 or R70 and R68, together with the atom(s) to which they are attached, form an substituted or unsubstituted 5-, 6-, or 7-membered ring.