Synthetic pathway of [2,4-dichloro-6-(3,5-dichloro-2-hydroxybenzamido)phenoxy]acetic acid

V. G. Dudarev; Дударев Владимир Геннадьевич; M. I. Vasendin; Васендин М. И.; A. V. Moskvin; Москвин Андрей Вадимович

doi:10.31857/S0514749224070074

Synthetic pathway of [2,4-dichloro-6-(3,5-dichloro-2-hydroxybenzamido)phenoxy]acetic acid

Autores: Dudarev V.G.¹, Vasendin M.I.¹, Moskvin A.V.¹
Afiliações:
1. St. Petersburg State Chemical and Pharmaceutical University
Edição: Volume 60, Nº 7 (2024)
Páginas: 875-882
Seção: Articles
URL: https://modernonco.orscience.ru/0514-7492/article/view/676689
DOI: https://doi.org/10.31857/S0514749224070074
EDN: https://elibrary.ru/RBIIRG
ID: 676689

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Resumo

Synthetic route of 3,5-dichlorosalicylic acid anilide containing carboxymethoxy-group in aniline fragment in ortho-position to amide group was proposed. The intermediate was 2-(2-nitro-4,6-dichlorophenoxy)-N,N-dimethylacetamide which was reduced to amine and acylated with 3,5-dichloro-2-hydroxybenzoyl chloride, and then protective N,N-dimethylamide group was selectively hydrolyzed in alkaline medium. Without protection of the carboxyl group, reaction with 3,5-dichloro-2-hydroxybenzoyl chloride affords mainly 6,8-dichloro-2H-1,4-benzoxazin-3(4H)-one.

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salicylanilides, reduction of nitro group, alkylation of nitrophenols, interphase catalysis, acylation, protecting groups

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Deng W., Guo Z., Guo Y., Feng Z., Jiang Y., Chu F. Bioorg. Med. Chem. Lett. 2006, 16, 469. doi: 10.1016/j.bmcl.2005.06.088
Gargantilla M., Persoons L., Kauerová T., del Río N., Daelemans D., Priego E.-M., Kollar P., Pérez-Pérez M.-J. Pharmaceuticals. 2022, 15, 835. doi: 10.3390/ph15070835
Steffen J. D., Coyle D. L., Damodaran K., Beroza P., Jacobson M. K. J. Med. Chem. 2011, 54, 5403. doi: 10.1021/jm200325s
Brown M.E., Fitzner J.N., Stevens T., Chin W., Wright C.D., Boyce J.P. Bioorg. Med. Chem. 2008, 16, 8760. doi: 10.1016/j.bmc.2008.07.024
Imramovský A., Pauk K., Pejchal V., Hanusek J. Mini-Rev. Org. Chem. 2011, 8, 211. doi: 10.2174/157019311795177808
Patel E.N., Lin L., Sneller M.M., Eubanks L.M., Tepp W.H., Pellett S., Janda K.D. ACS Infect. Dis. 2022, 8, 1637. doi: 10.1021/acsinfecdis.2c00230
Blake S., Shaabani N., Eubanks L.M., Maruyama J., Manning J.T., Beutler N., Paessler S., Ji H., Teijaro J.R., Janda K.D. ACS Infect. Dis. 2021, 7, 2229. doi: 10.1021/acsinfecdis.1c00253
Krátký M. and Vinšová J. Mini-Rev. Med. Chem. 2011, 11, 956. doi: 10.2174/138955711797068382
Xu J., Xue Y., Bolinger A.A.., Li J., Zhou M., Chen H., Li H., Zhou J. Med. Res. Rev. 2023, 43, 897. doi: 10.1002/med.21940
Августинович Д.Ф., Вишнивецкая Г.Б., Пирожкова Д.С., Цыганов М.А., Вавилин В.А., Пахарукова М.Ю., Шилов А.Г., Дударев В.Г., Мордвинов В.А. Сиб. науч. мед. ж. 2017, 37, 17.
Дударев В.Г., Васендин М.И., Москвин А.В., Лисовский Д.С., Колотилова Н.В., Лалаев Б.Ю. ЖОХ. 2023, 93, 1822. doi: 10.31857/S0044460X23120028 [Dudarev V.G., Vasen-din M.I., Moskvin A.V., Lysovsky D.S., Kolotilova N.V., Lalaev B.Y. Russ. J. Gen. Chem. 2023, 93. 3034.] doi: 10.1134/S1070363223120022
Cavill G.W.K., Ford, D.L. J. Chem. Soc. 1954, 565. doi : 10.1039/JR9540000565
Sartori E., Maillet M., France Paugam M., Nicolai E., Lawrence M. Пат. 2005/0124664 A1 (2005). США. CA 2005.
Liu Y., Donner P.L., Pratt J.K., Jiang W.W., Ng T., Gracias V., Baumeister S., Wiedeman P. E., Traphagen L., Warrior U., Maring C., Kati W.M, Djuric S.W., Molla A. Bioorg. Med. Chem. Lett. 2008, 18, 3173. doi: 10.1016/j.bmcl.2008.04.068
Nitta A., Iura Y., Inoue H., Sato I., Morihira K., Kubta H., Morokata T., Takeuchi M., Ohta M., Tsukamoto S., Imaoka T., Takahashi T. Bioorg. Med. Chem. Lett. 2012, 22, 6876. doi: 10.1016/j.bmcl.2012.09.035
Seidenfaden W., Albert H. Пат. 867244 (1953). ГДР. CA 1953.
Suezawa H., Hirota M., Yuzuri T., Hamada Y., Takeuchi I., Suigura M. Bull. Chem. Soc. Jpn. 2000, 73, 2335. doi: 10.1246/bcsj.73.2335
Vasiliev A.D., Solovyov L.A. Acta Cryst. 1999. C55, IUC9900004. doi: 10.1107/S0108270199099904
Zhang J. J. Mater. Sci. 2019, 54, 14197. doi: 10.1007/s10853-019-03864-3
Sharma S.K. Res. J. Chem. Sci. 2015, 5, 54-73.