An expedient synthesis of a picolinamide-based betain bearing a 3-sulfonatopropyl substituent

Kramarova, Eugeniya P.; Lyahmun, Dmitry N.; Tarasenko, Dmitry V.; Korlyukov, Alexander A.; Dorovatovskii, Pavel V.; Shmigol, Tatiana A.; Bylikin, Sergey Yu.; Baukov, Yuri I. and Negrebetsky, Vadim V. (2024). An expedient synthesis of a picolinamide-based betain bearing a 3-sulfonatopropyl substituent. Mendeleev Communications, 34(1) pp. 126–128.

DOI: https://doi.org/10.1016/j.mencom.2024.01.038

Abstract

3-[2-(Aminocarbonyl)pyridinium-1-yl]propane-1-sulfonate, a promising medicinal betain, was prepared by a one-pot synthesis with a 89% yield via N-alkylation of ethyl picolinate with 1,3-propanesultone in MeCN followed by ammonolysis. The reaction involving picolinamide in MeOH followed by the treatment with acetone afforded a novel 3,3-dimethyl- 1-oxo-2,3-dihydro-1H-imidazo[1,5-a]pyridin-4-ium 3-methoxypropane-1-sulfonate.

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