442129-37-5Relevant articles and documents
Improved Synthesis of 6-Chloro-5-methylpyridin-2-amine: A Key Intermediate for Making Lumacaftor
Jiang, Xiangrui,Shen, Jingshan,Tian, Guanghui,Zhang, Junchi,Zhu, Fuqiang
, p. 1175 - 1179 (2020)
A safe and efficient synthesis of 6-chloro-5-methylpyridin-2-amine, a key intermediate for lumacaftor, is described, which avoids the utilization of peroxide. In this four-step sequence, starting from 2-amino-6-chloropyridine, the crucial 5-position methylation was achieved via a Suzuki-Miyaura cross-coupling reaction. By adopting this synthetic route, 6-chloro-5-methylpyridin-2-amine was produced on a hectogram scale with 62.4% overall yield and 99.49% purity.
2 - Chloro -3 - methyl -6 - acyl aminopyridine and its preparation and use (by machine translation)
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Paragraph 0068; 0069; 0070, (2018/11/03)
The invention belongs to the field of pharmaceutical chemistry and chemical synthesis, in particular to the invention belongs to the field of pharmaceutical chemistry and chemical synthesis, in particular relates to a 2 - chloro - 3 - methyl - 6 - acyl aminopyridine and its preparation and use. The invention provides the following the general formula II of said 2 - chloro - 3 - methyl - 6 - acyl amino pyridine or its pharmaceutically acceptable salt, ester, prodrug or solvate thereof, and [...] fibrosis is an important intermediate of the active ingredient. Through formula II compound represented by the general formula IA or IB obtained compound can be directly used for preparing [...] fibrosis drug. The invention provides general formula IA or IB that the synthesis of the compounds has the following advantages: the security, the method is simple, high yield, it is suitable for industrial production. (by machine translation)
Synthesis of 5-bromo-6-methyl imidazopyrazine, 5-bromo and 5-chloro-6-methyl imidazopyridine using electron density surface maps to guide synthetic strategy
Harris, Anthony R.,Nason, Deane M.,Collantes, Elizabeth M.,Xu, Wenjian,Chi, Yushi,Wang, Zhihan,Zhang, Bingzhi,Zhang, Qingjian,Gray, David L.,Davoren, Jennifer E.
experimental part, p. 9063 - 9066 (2011/12/03)
Small heteroaromatic rings are valuable monomers in drug discovery that can enable rapid access to novel and desirable chemical space. Installation of a synthetic handle on a heteroaromatic core may be difficult if steric and electronic factors are not in alignment with the desired transformation. Described are practical routes for the construction of 5-bromo-6-methyl imidazopyrazine (1) as well as 5-bromo and 5-chloro-6-methyl imidazopyridines (2a and 2b), which were developed using electron density surface maps encoded with ionization potential to guide synthetic strategy.