- Improved Synthesis of 6-Chloro-5-methylpyridin-2-amine: A Key Intermediate for Making Lumacaftor
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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.
- Jiang, Xiangrui,Shen, Jingshan,Tian, Guanghui,Zhang, Junchi,Zhu, Fuqiang
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- Technological method for preparing 2- amino -6-5-methyl-substituted-pyridine (by machine translation)
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The reaction solvent of 2 - the method is reacted in a reaction solvent under the action, of 2 - an, acid anhydride and an acid,binding, agent and an amination reagent under the action. of an acid anhydride and 2 - an acid-binding agent and, an amination reagent, 2 -4 - 93/7, 99.8%, 70%. (by machine translation)
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Paragraph 0058-0060
(2020/01/12)
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- 2 - Chloro -3 - methyl -6 - acyl aminopyridine and its preparation and use (by machine translation)
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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)
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Paragraph 0061; 0062; 0063
(2018/11/03)
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- PROCESS FOR PREPARATION OF LUMACAFTOR
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The present invention relates to a process for the preparation of amorphous lumacaftor. The present invention relates to a process for the preparation of intermediate 6-amino-2- halo-3-methylpyridine compounds used in the preparation of lumacaftor. The present invention relates to lumacaftor hydrobromide, process for its preparation and conversion thereof to lumacaftor.
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Paragraph 0174
(2017/05/07)
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- Synthesis of 5-bromo-6-methyl imidazopyrazine, 5-bromo and 5-chloro-6-methyl imidazopyridine using electron density surface maps to guide synthetic strategy
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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.
- 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.
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experimental part
p. 9063 - 9066
(2011/12/03)
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- MODULATORS OF CFTR
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Compounds of the present invention, and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette ("ABC") transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator ("CFTR"). The present invention also relates to methods of treating CFTR mediated diseases using compounds of the present invention.
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