1206604-19-4Relevant articles and documents
Synthesis of Imatinib by C-N Coupling Reaction of Primary Amide and Bromo-Substituted Pyrimidine Amine
Wang, Cuiling,Bai, Xiao,Wang, Rui,Zheng, Xudong,Ma, Xiumei,Chen, Huan,Ai, Yun,Bai, Yajun,Liu, Yifeng
, p. 1918 - 1925 (2019)
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.
A PROCESS FOR THE PREPARATION OF IMATINIB
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Page/Page column 6, (2010/04/03)
A process for the preparation of Imatinib according to the invention consists in converting the 2-methyl-5-halogenoaniline of the Formula 2 into the salt of the 2-methyl-5- halogenophenylguanidine of the Formula 3, which is then condensed with the 3-diaIkylamino- ]-(pyridin-3-yI)prop-2-en-l-one of the Formula 4 to yield the N-(2-methyl-5- halogenophenyl)-4-(pyridin-3-yl)-pyrimidin-2-ylamine of the Formula 5, which is then reacted with 4-(4-methylpiperazin-l-ylmethyl)benzamide of the Formula 6, and the obtained Imatinib is optionally converted into its addition salt.