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

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?? inter-actions seem to be effective in stabilization of the crystal structure.

SUBMITTER: Koch P 

PROVIDER: S-EPMC2961725 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

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

Koch Pierre P   Bäuerlein Christiane C   Schollmeyer Dieter D   Laufer Stefan S  

Acta crystallographica. Section E, Structure reports online 20080607 Pt 7

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 be  ...[more]

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