Patent ID: 7767820

Claim:
A method for preparing a compound or pharmaceutically acceptable salt thereof that is {1-methyl-5-[2-(5-trifluoromethyl-1H-imidazol-2-yl)-pyridin-4-yloxy]-1H-benzoimidazol-2-yl}-(4-trifluoromethyl-phenyl)-amine the method comprising: (a) reacting a compound of Formula (II) with a compound of Formula (III) to provide a compound of Formula (IV) wherein b is 0, R 2 is methyl, Q is NH 2 or NO 2 ; one of L 1 or L 2 is halo and the other of L 1 or L 2 is OH or an anion thereof; Z is cyano, COOR 5 , CH 2 OR 5 , CHO, or imidazol-2-yl substituted with CF 3 and wherein R 5 is hydrogen or a hydroxy protecting group; (b) when in the compound of Formula (IV) Z is cyano, COOR 5 or CH 2 OR 5 , reacting said compound with a reducing agent to provide a compound of Formula (IV) wherein Z is CHO; (c) when in the compound of Formula (IV) Z is cyano, reacting the cyano functionality with an alkoxide to form an imidate, reacting the imidate with ammonium to form an amidino functionality and reacting said amidino functionality with a compound of Formula (Va) under imidazole ring forming conditions; or when in the compound of Formula (IV) Z is CHO, reacting said compound with a compound of Formula (Vb) to provide a compound of Formula (VI) wherein b is 0, c is 1, R 4 is CF 3 , X a in Formula (Va) is a leaving group and one of R 4p and R 4q in Formula (Vb) is H and the other of R 4p and R 4q is CF 3 , and X b is ═O or ═NHOH; (d) when in the compound of Formula (VI) Q is NO 2 , reacting said compound with a reducing agent to a compound of Formula (VI) wherein Q is NH 2 ; (e) reacting the compound of Formula (VI) wherein Q is NH 2 with a compound of Formula (VII) to provide a compound of Formula (VIII) or a tautomer thereof wherein a is 1, b is 0, c is 1, R 1 is 4-CF 3 , R 2 is methyl, and R 4 is CF 3 (f) reacting the compound of Formula (VIII) or a tautomer thereof with a desulfurizing agent to provide {1-methyl-5-[2-(5-trifluoromethyl-1H-imidazol-2-yl)-pyridin-4-yloxy]-1H-benzoimidazol-2-yl}-(4-trifluoromethyl-phenyl)-amine or its tautomer; and (g) optionally reacting {1-methyl-5-[2-(5-trifluoromethyl-1H-imidazol-2-yl)-pyridin-4-yloxy]-1H-benzoimidazol-2-yl}-(4-trifluoromethyl-phenyl)-amine or a tautomer thereof with an acid to give a pharmaceutically acceptable salt thereof.