Organic Process Research and Development p. 1918 - 1925 (2019)
Update date:2022-08-04
Topics:
Wang, Cuiling
Bai, Xiao
Wang, Rui
Zheng, Xudong
Ma, Xiumei
Chen, Huan
Ai, Yun
Bai, Yajun
Liu, Yifeng
A new method for imatinib synthesis is described by using the C-N coupling reaction of 4-(4-methylpiperazine-1-methyl)benzamide with N-(5-bromo-2-tolyl)-4-(3-pyridyl)pyrimidin-2-amine to form imatinib. In this synthetic route, the high efficiency and high selectivity of nano-ZnO as a catalyst is key to the mild hydrolysis of 4-(4-methylpiperazine-1-methyl)benzonitrile into the corresponding amide. The total imatinib yield was 51.3%, and the purity was 99.9%. This simple and effective synthetic pathway avoids gene-impurity production (as classified by the FDA Center for Drug Evaluation and Research), and the synthesis is environmentally friendly with a short reaction time.
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Doi:10.1021/jo902512q
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(2010)Doi:10.1016/j.bmcl.2009.11.014
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