December 28, 2023Methyl 6-aminonicotinate – preparation and application
Methyl 6-aminonicotinate [36052-24-1] or methyl 6-aminopyridine-3-carboxylate is white crystalline solid with the melting point of 154-156 °C.[1] It is a methyl ester of aminonicotinic acid.
Preparation of Methyl 6-aminonicotinate:
It can be easily prepared from 6-aminonicotinic acid by reaction with aqueous hydrogen chloride in methanol under reflux.[2]
Application:
Methyl 6-aminonicotinate is useful and versatile building block in the synthesis of various important pyridine derivatives. It was used in the synthesis of histone deacetylase 3 (HDAC3) selective inhibitors targeting breast cancer stem cells.[3] Methyl 6-aminonicotinate served as a substrate in the synthesis of glucokinase activators which may represent a new approach to diabetes therapy.[4]
Product categorization (Chemical groups):
Main category:
Second level:
Third level:
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[2] G. Yang, J. E. Golden Org. Lett. 2018, 20 (15), 4393. 10.1021/acs.orglett.8b01275
[3] H. Y. Hsieh, H. C. Chuang, F. H. Shen, K. Detroja, L. W. Hsin, C. S. Chen Eur. J. Med. Chem 2017, 140 (10), 42. doi:10.1016/j.ejmech.2017.08.069
[4] S. E. Badiger, K. F. Fosgerau, N. Vrang, V. D. Chaudhari, J. J. Naik, J. Auxcilia, R. R. Reddy, H. S. Subramanya, P. V. Reddy, B. N. S. Reddy Azine compounds as glucokinase activators 2008, Rheoscience A/S, WO2009083553A1.