Stereodynamics of Ar–CO rotation and conformational preferences of 2-amino-3-(2,4-difluorobenzoyl)-imidazo[1,2-a]pyridine
Carlos Jaramillo
1
,
Jose Eugenio De Diego
1
,
Alfonso Rivera-Sagredo
1
,
C. Hamdouchi
2
,
Juan F. Espinosa
1
1
Discovery Chemistry Research and Technologies, Lilly Research Laboratories, Centro de Investigación Lilly, Avda de la Industria 30, 28108 Alcobendas, Madrid, Spain
|
2
Discovery Chemistry Research and Technologies, Lilly Research Laboratories, Lilly Corporate Center, Indianapolis, IN 46285, USA
|
Publication type: Journal Article
Publication date: 2006-12-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
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.
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Jaramillo C. et al. Stereodynamics of Ar–CO rotation and conformational preferences of 2-amino-3-(2,4-difluorobenzoyl)-imidazo[1,2-a]pyridine // Tetrahedron. 2006. Vol. 62. No. 52. pp. 12415-12419.
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Jaramillo C., De Diego J. E., Rivera-Sagredo A., Hamdouchi C., Espinosa J. F. Stereodynamics of Ar–CO rotation and conformational preferences of 2-amino-3-(2,4-difluorobenzoyl)-imidazo[1,2-a]pyridine // Tetrahedron. 2006. Vol. 62. No. 52. pp. 12415-12419.
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TY - JOUR
DO - 10.1016/j.tet.2006.09.097
UR - https://doi.org/10.1016/j.tet.2006.09.097
TI - Stereodynamics of Ar–CO rotation and conformational preferences of 2-amino-3-(2,4-difluorobenzoyl)-imidazo[1,2-a]pyridine
T2 - Tetrahedron
AU - Jaramillo, Carlos
AU - De Diego, Jose Eugenio
AU - Rivera-Sagredo, Alfonso
AU - Hamdouchi, C.
AU - Espinosa, Juan F.
PY - 2006
DA - 2006/12/01
PB - Elsevier
SP - 12415-12419
IS - 52
VL - 62
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2006_Jaramillo,
author = {Carlos Jaramillo and Jose Eugenio De Diego and Alfonso Rivera-Sagredo and C. Hamdouchi and Juan F. Espinosa},
title = {Stereodynamics of Ar–CO rotation and conformational preferences of 2-amino-3-(2,4-difluorobenzoyl)-imidazo[1,2-a]pyridine},
journal = {Tetrahedron},
year = {2006},
volume = {62},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/j.tet.2006.09.097},
number = {52},
pages = {12415--12419},
doi = {10.1016/j.tet.2006.09.097}
}
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MLA
Copy
Jaramillo, Carlos, et al. “Stereodynamics of Ar–CO rotation and conformational preferences of 2-amino-3-(2,4-difluorobenzoyl)-imidazo[1,2-a]pyridine.” Tetrahedron, vol. 62, no. 52, Dec. 2006, pp. 12415-12419. https://doi.org/10.1016/j.tet.2006.09.097.