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Stereodynamics of Ar–CO rotation and conformational preferences of 2-amino-3-(2,4-difluorobenzoyl)-imidazo[1,2-a]pyridine |
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| Authors: | Carlos Jaramillo, Jos Eugenio de Diego, Alfonso Rivera-Sagredo, Chafiq Hamdouchi,Juan F. Espinosa |
| Affiliation: | aDiscovery Chemistry Research and Technologies, Lilly Research Laboratories, Centro de Investigación Lilly, Avda de la Industria 30, 28108 Alcobendas, Madrid, Spain bDiscovery Chemistry Research and Technologies, Lilly Research Laboratories, Lilly Corporate Center, Indianapolis, IN 46285, USA |
| Abstract: | The dynamic NMR analysis of 2, a subunit of a new class of cyclic-dependent kinase inhibitors, reveals that the compound exists as two conformational isomers, Z and E, in acetone, as a consequence of the restricted rotation about the imidazopyridine–carbonyl bond. The less hindered Z-rotamer is the most abundant conformer (85:15 Z/E at 233 K) and the free energy of activation of the interconversion is 13.2 kcal mol−1. The rotamer ratio and the interconversion barrier are similar in other solvents, such as CD3OD and CDCl3. |
| Keywords: | Ar–CO rotation Conformational analysis Dynamic NMR Imidazopyridine CDK inhibitors |
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