Benzo-fused compounds for use in treating metabolic disorders

A method of synthesizing a compound of formula XV, the compound of formula XV having the following structure:

• the method comprising:
• (a) reacting a compound of formula XIII with a compound of formula XIV to produce the compound of formula XV, wherein the compounds of formula XIII and XIV have the following structures:
• wherein,
• Alk is a straight or branched chain alkyl group having from 1 to 8 carbon atoms;
• R1 is selected from cyano, aryl, heteroaryl, heterocycloalkyl, (C2-C8)alkenyl, (C3-C8)alkenyl, (C2-C8)alkynyl, (C3-C8)alkynyl, or —C(O)NR2R3;
• R2 and R3 are independently selected from hydrogen, aryl, heteroaryl, (C1-C8)alkyl, (C2-C8)heteroalkyl, (C3-C8)cycloalkyl, or (C3-C8)heterocycloalkyl;
• optionally, R2 and R3 are combined to form a 4-, 5-, 6- or 7-membered ring containing the nitrogen atom to which they are attached comprising from 0 to 2 additional heteroatoms selected from N, O, or S;
• and;
• R5 is independently selected from (C1-C6)alkyl, halogen, (C1-C6)alkoxy, cyano, or nitro;
• p is selected from 0, 1, 2, 3, or 4;
• z is selected from 1, 2, or 3;
• R4′ is independently selected from substituted (C1-C6)alkyl, —R′, —OR′, ═O, ═NR′, ═N—OR′, —NR′R″, —SR′, halogen, —OC(O)R′, —C(O)R′, —CO2R′, —CONR′R″, —OC(O)NR′R″, —NR″C(O)R′, —NR′—C(O)NR″R′″, —NR′—SO2NR″R′″, —NR″CO2R′, —NH—C(NH2)═NH, —NR′C(NH2)═NH, —NH—C(NH2)═NR′, —SiR′R″R′″, —S(O)R′, —SO2R′, —SO2NR′R″, —NR″SO2R, —CN, —(C2-C5)alkynyl, —(C2-C5)alkenyl, or —NO2, wherein R′, R″ and R′″ are each independently selected from hydrogen, unsubstituted (C1-C8)alkyl or heteroalkyl, unsubstituted aryl, aryl substituted with one to three halogens, unsubstituted alkyl, alkoxy or thioalkoxy groups, halo(C1-C4)alkyl, or aryl-(C1-C4)alkyl groups;
• n′ is 0, 1, 2, or 3;
• m is 1,2,3, or 4;
• one of R6 and R6′ is L1 or Q, if L1 is a bond, and the others of R6 and R6′ are independently selected from H, (C1-C6)alkyl, halogen, (C1-C6)alkoxy, cyano, or nitro, wherein one of R6 and one of R6′ on adjacent or non-adjacent carbon atoms, or on the same carbon atom may join together to form a C5-C8 cycloalkane ring, or two of R6 or two of R6′, on adjacent or non-adjacent carbon atoms, may join together to form a C5-C8 cycloalkane ring;
• L1 is selected from a bond, (C1-C4)alkylene, (C2-C4)heteroalkylene, O, S(O)k, N(Ra), C(O)—(C5-C7)heterocycloalkylene, (C1-C4)alkylene-SO2N(Rb), (C1-C4)alkylene-N(Rb)SO2, or C(O)N(Rb);
• Ra is selected from hydrogen, (C1-C6)alkyl, aryl(C1-C3)alkyl, or (C2-C6)heteroalkyl;
• Rb is selected from hydrogen, (C1-C6)alkyl, or (C2-C6)heteroalkyl;
• Q is selected from hydrogen, aryl, heteroaryl, (C1-C6)alkyl, or (C2-C6)heteroalkyl;
• W is a leaving group;
• and
• further wherein, the compounds of formula XIII and XV can be a mixture of compounds having the R and S stereochemistry at the carbon bonded to R1, can have the R stereochemistry at the carbon bonded to R1, or can have the S stereochemistry at the carbon bonded to R1.