125743-63-7Relevant articles and documents
A novel synthesis of imatinib and its intermediates
Liu, Haiyan,Xia, Wenpin,Luo, Yu,Lu, Wei
, p. 907 - 911 (2010)
A convenient method has been developed for the synthesis of imatinib and two of its intermediates. N-(2-Methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidin amine, obtained from 2-(methylsulfonyl)-4-(3-pyridyl)pyrimidine via nucleophilic substitution, was reduced by N2H4H2O/FeCl 3·6H2O/C in 92% yield. The resulting amine was condensed with 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride, which was prepared from 4-(chloromethyl)benzonitrile via substitution and hydrolysis reactions, to provide the final product imatinib in good yield and high purity. Springer-Verlag 2010.
Accessing Aliphatic Amines in C-C Cross-Couplings by Visible Light/Nickel Dual Catalysis
Badir, Shorouk O.,Dong, Weizhe,Molander, Gary A.,Zhang, Xuange
supporting information, p. 4250 - 4255 (2021/06/27)
A general aminoalkylation of aryl halides was developed, overcoming intolerance of free amines in nickel-mediated C-C coupling. This transformation features broad functional group tolerance and high efficiency. Taking advantage of the fast desilylation of α-silylamines upon single-electron transfer (SET) facilitated by carbonate, α-amino radicals are generated regioselectively, which then engage in nickel-mediated C-C coupling. The reaction displays high chemoselectivity for C-C over C-N bond formation. Highly functionalized pharmacophores and peptides are also amenable.
Cyano-pyrrolo-heteroaryl derivative, preparation method thereof and application of derivative to medicine
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Paragraph 0254; 0255; 0256; 0257; 0258-0261, (2019/10/23)
The invention relates to a cyano-pyrrolo-heteroaryl derivative, a preparation method thereof and an application of the derivative to medicine, and particularly relates to a novel cyano-pyrrolo-heteroaryl derivative as shown in a general formula (I), a pre
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 (2019/09/07)
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.