A scalable synthesis of a histamine H3 receptor antagonist.
Starting from 1-methylimidazole, a concise, scalable, three-step synthesis of the title compound is described. The required 2-chloroimidazole was prepared in very good yield by halogen-metal exchange between the 2-lithio derivative and hexachloroethane.
Mani
Neelakandha S
NS
Department of Drug Discovery, Johnson & Johnson Pharmaceutical Research and Development, L.L.C., 3210 Merryfield Row, San Diego, California 92121, USA. nmani@prdus.jnj.com
Jablonowski
Jill A
JA
Jones
Todd K
TK
D020650:Combinatorial Chemistry Techniques; D006633:Histamine Antagonists / Q000138:chemical synthesis* / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D018100:Receptors, Histamine H3 / Q000187:drug effects*
C494220:(4-chlorophenyl)-(2-(2-isopropylpiperidin-4-ylmethoxy)-3-methyl-3H-imidazol-4-yl)methanone; D006633:Histamine Antagonists; D007093:Imidazoles; D018100:Receptors, Histamine H3