133627-45-9Relevant articles and documents
A concise synthesis of 2-chloro-3-amino-4-methylpyridine
Ge, Xin,Chen, Han-Geng,Cao, Chang-Hui,Liu, Jin-Qiang,Qian, Chao,Chen, Xin-Zhi
, p. 599 - 604 (2011)
An improved and commercially valuable process is developed for the scalable synthesis of 2-chloro-3-amino-4-methylpyridine (CAPIC), a key intermediate of Nevirapine. The synthesis was accomplished in four steps, featuring condensation starting from 4,4-dimethoxyl-2-butanone and cyanoacetamide with ammonium acetate and acetic acid as catalysts. The total yield of the process is 62.1%. The pure CAPIC sample was confirmed with FTIR, 1H NMR, and 13C NMR spectra.
Synthesis of 2-cyanoacrylates containing pyridinyl moiety under ultrasound irradiation
Zhang, Huiping,Song, Baoan,Zhong, Huimin,Yang, Song,Jin, Linhong,Hu, Deyu,He, Wei
, p. 1211 - 1214 (2005)
Reaction of ethyl cyanoacetate with carbon disulfide and dimethyl sulfate in the presence of sodium methoxide in anhydrous methanol yields ethyl 2-cyano-3,3-dimethyl-thioacrylate, followed by the nucleophilic substitution with 2-amino-3-chloro-4- methylpy
Synthesis, docking study and kinase inhibitory activity of a number of new substituted pyrazolo[3,4-c]pyridines
Sklepari, Meropi,Lougiakis, Nikolaos,Papastathopoulos, Athanasios,Pouli, Nicole,Marakos, Panagiotis,Myrianthopoulos, Vassilios,Robert, Thomas,Bach, Stéphane,Mikros, Emmanuel,Ruchaud, Sandrine
, p. 66 - 81 (2017)
A series of new pyrazolo[3,4-c]pyridines bearing various 1, 3, 5 or 1, 3, 7 pattern substitutions, were designed and synthesized. Some of them showed interesting inhibitory activity mainly against glycogen synthase kinase 3 (GSK3)α/β as well as against cdc2-like kinases 1 (CLK1) and dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A), with good selectivity and remarkable structure-activity relationships (SARs), without being cytotoxic. Molecular simulations in correlation with biological data revealed the importance of the existence of N1-H as well as the absence of a bulky 7-substituent.
Improved synthesis of 2-chloro-3-amino-4-methylpyridine
Zhao, Qian,Chen, Han-Geng,Qian, Chao,Chen, Xin-Zhi
, p. 145 - 148 (2013)
2-Chloro-3-amino-4-methylpyridine (), a key intermediate in the synthesis of nervirapine, was prepared from 2-cyanoacetamide and 4,4-dimethoxyl-2-butanone via condensation, cyclization, one-pot reaction of chlorination and hydrolysis, and Hofmann reaction. Utilization of the quadratic orthogonal test resulted in a high yield (62.1%) of the whole process.
DIARYLTHIOHYDANTOIN COMPOUND AS ANDROGEN RECEPTOR ANTAGONIST
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Paragraph 0205-0207, (2020/07/07)
The present application belongs to the field of medicine. In particular, the present application relates to a diarylthiohydantoin compound as an androgen receptor antagonist or a pharmaceutically acceptable salt thereof, a preparation method of the same, a pharmaceutical composition comprising the compound, and a use thereof in treating a cell proliferative disease mediated by androgen. The compound of the present application has good antagonistic effect on androgen receptor and exhibits excellent antitumor effect.
4-methylpiperidine-3-ketone and simple preparation method of 4-methylpiperidine-3-ketone derivative
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Paragraph 0095-0100, (2019/11/04)
The invention relates to 4-methylpiperidine-3-ketone and a simple preparation method of a 4-methylpiperidine-3-ketone derivative. According to the 4-methylpiperidine-3-ketone and the simple preparation method of the 4-methylpiperidine-3-ketone derivative, 1-nitro-3-methyl-5-hydroxy n-amyl-2-ketone is prepared by using a reaction of alpha-methyl-gamma-butyrolactone and nitromethane, then 1-nitro-3-methyl-5-protection oxy-n-pentyl-2-ketone is obtained through sulfonyl chloride reagent protection hydroxide radical, then nitro is reduced to amino through hydrogenation, and meanwhile 4-methylpiperidine-3-ketone is obtained through cyclization. The invention further provides a method for preparing 2-chlorin-3-amino-4-methylpyridine and N-benzyl-4-methylpiperidine-3-ketone from 4-methylpiperidine-3-ketone. Raw materials used in the simple preparation method and the method are cheap and readily available, the condition is mild, operation is simple and convenient and safe, reaction selectivityis high, the product yield and purity are high, the cost is low, the amount of "three wastes" is low, and environmental protection is realized.
Increasing global access to the high-volume HIV drug nevirapine through process intensification
Verghese, Jenson,Kong, Caleb J.,Rivalti, Daniel,Yu, Eric C.,Krack, Rudy,Alcázar, Jesus,Manley, Julie B.,McQuade, D. Tyler,Ahmad, Saeed,Belecki, Katherine,Gupton, B. Frank
supporting information, p. 2986 - 2991 (2017/07/24)
Access to affordable medications continues to be one of the most pressing issues for the treatment of disease in developing countries. For many drugs, synthesis of the active pharmaceutical ingredient (API) represents the most financially important and technically demanding element of pharmaceutical operations. Furthermore, the environmental impact of API processing has been well documented and is an area of continuing interest in green chemical operations. To improve drug access and affordability, we have developed a series of core principles that can be applied to a specific API, yielding dramatic improvements in chemical efficiency. We applied these principles to nevirapine, the first non-nucleoside reverse transcriptase inhibitor used in the treatment of HIV. The resulting ultra-efficient (91% isolated yield) and highly-consolidated (4 unit operations) route has been successfully developed and implemented through partnerships with philanthropic entities, increasing access to this essential medication. We anticipate an even broader global health impact when applying this model to other active ingredients.
Synthesis and Antiproliferative Activity of New pyrazolo[3,4-c]pyridines
Gavriil, Efthymios-Spyridon,Lougiakis, Nikolaos,Pouli, Nicole,Marakos, Panagiotis,Skaltsounis, Alexios-Leandros,Nam, Sangkil,Jove, Richard,Horne, David,Gioti, Katerina,Pratsinis, Harris,Kletsas, Dimitris,Tenta, Roxane
, p. 365 - 374 (2017/06/21)
Background: Several pyrazolopyridines possess promising pharmacological activities, mainly attributed to their antagonistic nature towards the natural purines in many biological processes. Cytotoxicity and anticancer potential of this class of compounds a
Preparation method for nevirapine intermediate
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Paragraph 0076-0078, (2017/05/27)
The invention relates to a preparation method for an intermediate, i.e., 2-chloro-3-amino-4-methylpyridine, of an anti-AIDs drug nevirapine. The intermediate has a chemical structural formula I as described in the specification. The preparation method is characterized in that 4-methylpyridine is subjected to halogenation, ammonia substitution and chlorination so as to prepare 2-chloro-3-amino-4-methylpyridine. The preparation reactions are as shown in the specifications, wherein X is bromine or chlorine; a halogenation condition is Br2/AlCl3/95-105 DEG C, Br2/AlCl3/MBr/110 to 130 DEG C (wherein M is Li, Na or K), Br2/Fe/135-145 DEG C, Cl2/AlCl3, Br2/FeCl3 or Br2/SnCl4; an ammonia substitution condition is NH3(g)/CuSO4/CH3OH/170-190 DEG C, NH3(aq)/CuSO4/170-190 DEG C, or NaNH2; and a chlorination reaction condition is Cl2/AlCl3 or HCl/H2O2/30-50 DEG C.
Experimental study on seawater applications in organic reactions
Liu, Gang,Qiu, Mingxiang,Sun, Lin,Wen, Quanwu,Xu, Shengguang,Wang, Xuyuan,Wang, Peng
, p. 44 - 48 (2015/12/31)
Background: Total water resources account for only 2.5% of freshwater on earth, and only 1% of total water resources can be exploited by humans. The development of practical methods of seawater desalination and comprehensive utilization technology can help address the shortage of freshwater resources in the world, and achieve sustainable use of water resources to ensure sustainable development in a society. Direct seawater utilization currently involves industrial cooling water, water for agricultural irrigation, and flushing water. Applications in aqueous phase organic reactions, particularly the direct use of seawater in industrial organic synthesis reactions, are seldom reported. Methods: we used seawater instead of freshwater in selected basic organic chemical reactions. The application of seawater in aqueous phase organic reactions was systematically investigated. Six types of reactions were studied using freshwater and seawater, namely, preparation of acetanilide, synthesis of mandelic acid, Cannizzaro reaction, Hofmann degradation reaction, preparation of quinazolin-4-one, and preparation of adipic acid. Results: Seven organic compounds were produced. Results show that some organic reactions could directly use seawater or treated seawater as an alternative to freshwater. The yields of the reactions using seawater could be compared with literature values, or were even better than literature values. Conclusion: This research provides new opportunities for the comprehensive utilization of seawater. Some organic reactions could directly use seawater or treated seawater instead of freshwater. The use of seawater instead of freshwater for organic reactions in industrial production may greatly conserve freshwater resources and protect the environment.
