Methyl 4-[5-(4-fluoro-phen-yl)-4-(pyridin-4-yl)-1H-imidazol-2-ylsulfan-yl]butanoate

Acta Crystallogr Sect E Struct Rep Online. 2008 Jun 7;64(Pt 7):o1183-4. doi: 10.1107/S1600536808016000.

Abstract

The title compound, C(19)H(18)FN(3)O(2)S, was synthesized in the course of studies on 2-alkyl-sufanylimidazoles as p38 mitogen-activated protein kinase inhibitors. The synthesis was achieved by nucleophilic substitution of 4-(4-fluoro-phen-yl)-5-(pyridin-4-yl)-1,3-dihydro-imidazole-2-thione with methyl 4-bromo-butanoate. The five-membered heterocycle makes dihedral angles of 32.4 (2) and 18.3 (2)° with the fluoro-phenyl and pyridinyl rings, respectively, indicating a low degree of conjugation between these rings. Intra-molecular C-H⋯N and inter-molecular N-H⋯N hydrogen bonds as well as C-H⋯π inter-actions seem to be effective in stabilization of the crystal structure.