Title of article :
A solid solution of ethyl and d3-methyl 2-[(4-methylpyridin-2-yl)amino]-4-(pyridin-2-yl)thiazole-5-carboxylate
Author/Authors :
Beuchela, Andreas Institut für Pharmazie, Germany , Goddard, Richard Max-Planck-Institut für Kohlenforschung, Germany , Imming, Peter Institut für Pharmazie, Germany , Seidel, Rüdiger W. Institut für Pharmazie, Germany
Abstract :
The synthesis of ethyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole- 5-carboxylate via the Hantzsch reaction and partial in situ transesterification during recrystallization from methanol-d4 to the d3-methyl ester, resulting in the title solid solution, ethyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole-5-carboxylate–d3-methyl 2-[(4-methylpyridin-2-yl)amino)-4-(pyridin-2-yl)thiazole-5-carboxylate (0.88/0.12), 0.88C17H16N4O2S·0.12C16D3H11N4O2S, is reported. The refined ratio of ethyl to d3-methyl ester in the crystal is 0.880 (6):0.120 (6). The pyridine ring is significantly twisted out of the plane of the approximately planar picoline thiazole ester moiety. N—H⋯N hydrogen bonds between the secondary amino group and the pyridine nitrogen atom of an adjacent symmetry-related molecule link the molecules into polymeric hydrogen-bonded zigzag tapes extending by glide symmetry in the [001] direction. There is structural evidence for intramolecular N⋯S chalcogen bonding and intermolecular weak C—H⋯O hydrogen bonds between adjacent zigzag tapes.
Keywords :
2- crystal structure , aminothiazole , Hantzsch reaction , heterocycle , solid solution , hydrogen bonding
Journal title :
Acta Crystallographica Section E: Crystallographic Communications