- 4 - Fluorine substituted aryl amine compound and synthesis method thereof
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The invention discloses a synthesis method of 4 -fluorine substituted aryl amine compound, which comprises the following steps: 1) taking acyl-protected phenylhydroxylamine as a substrate, and generating 4 -fluorine substituted aniline compound under basic conditions by taking sulfonyl fluoride as a fluorine source in a polar solvent. 2) The deprotection is carried out under dilute acid conditions or Pd by catalytic hydrogenation to give the 4 - fluorine-substituted aryl amine compound. 4 - Fluorine substituted aniline compounds which are synthesized by the invention greatly increase the lipophilic property due to the introduction of fluorine atoms, and can be widely applied to preparation of fluorine-containing drugs and pesticide and dye intermediates. , The adopted raw materials are industrial products, are cheap and easily available, and are commercially available. 4 - Fluoroaryl aniline prepared by the method is high in yield, and the product with the purity 90% can be obtained in a yield of more than ≥ 99%. The method is simple to operate and low in cost, is very suitable for industrialization, and can be widely popularized and used.
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Paragraph 0060-0062
(2021/09/22)
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- Visible-light-induced Pd-catalyzed: Ortho -trifluoromethylation of acetanilides with CF3SO2Na under ambient conditions in the absence of an external photocatalyst
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A visible-light-induced Pd-catalyzed ortho-trifluoromethylation of acetanilides with CF3SO2Na was developed. The reaction proceeded smoothly at room temperature in air without any external photocatalyst or additive, providing the desired products in moderate to good yields with good functional group tolerance and regioselectivity.
- Zou, Long,Li, Pinhua,Wang, Bin,Wang, Lei
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supporting information
p. 3737 - 3740
(2019/04/01)
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- Preparation 2-trifluoromethyl-4-substituted aniline compounds
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The invention relates to a method for preparing 2-trifluoromethyl-4-substituted phenylamine and 2-trifluoromethyl-4-substituted acetanilide. The method for preparing the2-trifluoromethyl-4-substituted phenylamine and 2-trifluoromethyl-4-substituted acetanilide comprises the following main step: in the presence of sodium trifluoromethanesulfonate and tert-butyl hydroperoxide but no metal salt catalyst and under the stirring condition, maintaining a 4-substituted phenylamine compound (concrete structure shown in a formula II is described in the specification) in a reaction medium of mixture composed of dichloromethane and water at the temperature of 0-25 DEG C for 72-120 hours, so that the 2-trifluoromethyl-4-substituted phenylamine target product is obtained. The preparation method provided by the invention has potential commercial value.
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Paragraph 0023-0026
(2017/02/23)
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- Copper-free direct C-H trifluoromethylation of acetanilides with sodium trifluoromethanesulfinate
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A copper-free direct C-H ortho trifluoromethylation of electron-deficient 4-substituted acetanilides using Langlois reagent (NaSO2CF3) as the CF3 source in the presence of tert-butyl hydroperoxide (tBuOOH, TBHP) was developed.
- Wu, Mingxi,Ji, Xinfei,Dai, Wenpeng,Cao, Song
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p. 8984 - 8989
(2015/01/09)
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- Palladium-catalyzed trifluoromethylation of aromatic C-H bond directed by an acetamino group
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The first palladium-catalyzed ortho-trifluoromethylation of the aromatic C-H bond directed by an acetamino group is reported. This method provides an efficient and green approach to synthesize the highly biological potential key structure of ortho-CF3 acetanilides and anilines.
- Zhang, Li-Sheng,Chen, Kang,Chen, Guihua,Li, Bi-Jie,Luo, Shuang,Guo, Qing-Yun,Wei, Jiang-Bo,Shi, Zhang-Jie
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supporting information
p. 10 - 13
(2013/04/10)
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- Novel Compounds
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The present invention relates to the new compounds of general formula I wherein A, U, V, X, Y, R1, R2 and R3 are defined as stated hereinafter, the tautomers, the isomers thereof, the diastereomers, the enantiomers, the hydrates, the mixtures and the salts thereof as well as the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, medicaments containing these compounds, their use and processes for preparing them.
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Page/Page column 80
(2012/04/18)
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- NOVEL HETEROCYCLE COMPOUNDS
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The present invention relates to novel compounds which are antagonist or inverse agonists at an opioid receptor. Such compounds are useful in the treatment of obesity and related diseases and/or conditions in mammals, particularly humans. Methods of making and using such compounds are also disclosed.
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Page/Page column 27
(2009/04/24)
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- Glycine receptor antagonists and the use thereof
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Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, inducing anesthesia and treating psychosis are disclosed by administering to an animal in need of such treatment a compound having high affinity for the glycine binding site, lacking PCP side effects and which crosses the blood brain barrier of the animal. Also disclosed are novel 1,4-dihydroquinoxaline-2,3-diones, and pharmaceutical compositions thereof. Also disclosed are highly soluble ammonium salts of 1,4-dihydroquinoxaline-2,3-diones.
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- Synthesis and structure-activity relationships of substituted 1,4- dihydroquinoxaline-2,3-diones: Antagonists of N-methyl-D-aspartate (NMDA) receptor glycine sites and non-NMDA glutamate receptors
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A series of mono-, di-, tri-, and tetrasubstituted 1,4- dihydroquinoxaline-2,3-diones (QXs) were synthesized and evaluated as antagonists at N-methyl-D-aspartate (NMDA)/glycine sites and α-amino-3- hydroxy-5-methylisoxazole-4-propionic acid-preferring non-NMDA receptors. Antagonist potencies were measured by electrical assays in Xenopus oocytes expressing rat whole brain poly(A)+ RNA. Trisubstituted QXs 17a (ACEA 1021), 17b (ACEA 1031), 24a, and 27, containing a nitro group in the 5 position and halogen in the 6 and 7 positions, displayed high potency (K(b) ~ 6-8 nM) at the glycine site, moderate potency at non-NMDA receptors (K(b) = 0.9-1.5 μM), and the highest (120-250-fold) selectivity in favor of glycine site antagonism over non-NMDA receptors. Tetrasubstituted QXs 17d,e were more than 100-fold weaker glycine site antagonists than the corresponding trisubstituted QXs with F being better tolerated than Cl as a substituent at the 8 position. Di- and monosubstituted QXs showed progressively weaker antagonism compared to trisubstituted analogues. For example, removal of the 5-nitro group of 17a results in a ~100-fold decrease in potency (10a,b,z), while removal of both halogens from 17a results in a ~3000-fold decrease in potency (10v). In terms of steady-state inhibition, most QX substitution patterns favor antagonism at NMDA/glycine sites over antagonism at non-NMDA receptors. Among the QXs tested, only 17i was slightly selective for non- NMDA receptors.
- Keana,Kher,Sui Xiong Cai,Dinsmore,Glenn,Guastella,Huang,Ilyin,Lu,Mouser,Woodward,Weber
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p. 4367 - 4379
(2007/10/02)
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