Patent ID: 7585979
Filing Date: 2009-09-08
Classification: C07D

Abstract:
1. A method of preparing N-hydroxy-4-{5-[4-(5-isopropyl-2-methyl-1,3-thiazol-4-yl)phenoxy]pentoxy}benzamidine (1), comprising steps of: 1) reacting anisole (2) with isovaleryl chloride, to prepare 1-(4-methoxy-phenyl)-3-methyl-butan-1-one (3); 2) reacting the compound (3) prepared in step 1) with bromine, sulfuryl chloride, N-bromosuccinimide or copper bromide, to prepare 2-bromo-1-(4-methoxy-phenyl)-3-methyl-butan-1-one (4); 3) reacting the compound (4) prepared in step 2) with thioacetamide, to prepare 5-isopropyl-4-(4-methoxy-phenyl)-2-methyl-thiazole (5); 4) reacting the compound (5) prepared in step 3) with bromic acid and acetic acid, sodium cyanide and dimethylsulfoxide, or tetrabutylammonium iodide and boron trifluoride•diethylether, to prepare 4-(5-isopropyl-2-methyl-1,3-thiazol-4-yl)-phenol (6); 5) reacting the compound (6) obtained in step 4) with 4-(5-chloro-pentoxy)-benzonitrile (8) or with 4-(5-iodo-pentoxy)-benzonitrile (9), to prepare 4-{5-[4-(5-isopropyl-2-methyl-1,3-thiazol-4-yl)-phenoxy]-pentoxy}-benzonitrile (10), and 6) reacting the compound (10) prepared in step 5) with hydroxylamine hydrochloride and a base, to prepare N-hydroxy-4-{5-[4-(5-isopropyl-2-methyl-1,3-thiazol-4-yl)phenoxy]pentoxy}benzamidine (1).