- Synthesis method of aminopyridine compounds
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The invention provides a synthesis method of aminopyridine compounds. The synthesis method of the aminopyridine compounds comprises the following steps: under a heating condition, halogenated pyridineorganic matters and an ammoniation reagent are subjected to an ammoniation reaction to obtain an ammoniated product system, wherein in the ammoniation reaction, the temperature of the ammoniation reaction is 200-240 DEG C, and the ammoniation reagent is in a solid state and can be decomposed to generate ammonia gas; and the ammoniated product system is sequentially purified and salified to obtainthe aminopyridine compounds. The synthesis method does not need to add a solvent, so that the yield of three wastes can be greatly reduced; the type of the ammonification reagent and the ammonification reaction temperature are limited during the reaction process, such that the high reaction rate and the high conversion rate can be obtained without the addition of the catalyst, and the purification and salification process after the ammonification reaction is simple and has the good separation effect so as to substantially reduce the production cost and improve the product yield and the product purity. In addition, the synthesis method also has the advantages of good repeatability and the like.
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Paragraph 0039-0052; 0071-0078
(2020/10/14)
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- Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters
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A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.
- Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.
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supporting information
p. 482 - 487
(2019/01/04)
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- Preparation method of 2-amino substituted six-membered nitrogen-containing heterocycle complex
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The invention discloses a preparation method of a 2-amino substituted six-membered nitrogen-containing heterocycle complex. The preparation method comprises the following steps: mix 2-fluorine substituted six-membered nitrogen-containing heterocycle complex and amidine hydrochloride salt compound, and then react under the action of a alkaline substance to obtain a 2-amino substituted six-memberednitrogen-containing heterocycle complex. Preferably, the 2-amino substituted six-membered nitrogen-containing heterocycle complex is a 2-amino pyridine compound, a 2-aminopyrimidine compound or a 2-aminopyrazine compound. Compared with the prior art, the method has the advantages of simple synthesis conditions, less reaction steps, mild reaction conditions, low cost of the catalyst used, less waste discharge and good functional group tolerance.
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Paragraph 0043; 0044
(2019/02/08)
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- Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride
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Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products.
- Li, Yibiao,Huang, Shuo,Liao, Chunshu,Shao, Yan,Chen, Lu
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supporting information
p. 7564 - 7567
(2018/11/02)
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- PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS
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The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).
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Page/Page column 51; 53
(2017/04/11)
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- MK2 INHIBITORS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 001189
(2014/10/03)
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- Theoretical and experimental NMR data of 3,5-dinitro-2-(2-phenylhydrazinyl) pyridine and of its 4- and 6-methyl derivatives
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3,5-Dinitro-2-(2-phenylhydrazinyl)pyridine and its methyl derivatives: 4-methyl-3,5-dinitro-2-(2-phenylhydrazinyl)pyridine and 6-methyl-3,5-dinitro-2- (2-phenylhydrazinyl)pyridine were synthesized and characterized by 1H NMR and 13C NMR. Calculations were also performed where the above molecules were optimized using the methods of density functional theory (DFT) with 6-31G(d,p) and 6-311G(d,p) basis sets. For all molecules studied, the lowest energy was obtained using the 6-311G(d,p) basis set. The GIAO/DFT (Gauge Invariant Atomic Orbitals/Density Functional Theory) calculations on the 6-311G and 6-311++G and 6-311G* basis sets were carried out to determine proton and carbon chemical shifts and to find they were close to the experimental values. It has been also found that intramolecular hydrogen bonding exists between hydrogen atom (in 2-NH group) and oxygen atom (pyridine-3-NO2). Moreover, resonances between pyridine ring and electron withdrawing 3-nitro group as well between that ring and the lone electron pair of NH group favor a co-planarity of the structure; this means a chelate ring created by above-mentioned intramolecular hydrogen bond is almost co-planar with pyridine ring.
- Wandas,Talik
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- A simple synthesis of aminopyridines: Use of amides as amine source
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A transition metal/microwave irradiation (or base) free synthesis of aminopyridines has been accomplished via C-N bond forming reaction between chloropyridine and a variety of simple amides under refuxing conditions.
- Kodimuthali, Arumugam,Mungara, Anitha,Prasunamba, Padala Lakshmi,Pal, Manojit
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experimental part
p. 1439 - 1445
(2010/11/04)
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- Imidazopyridines: A novel class of hNav1.7 channel blockers
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A series of imidazopyridines were evaluated as potential sodium channel blockers for the treatment of neuropathic pain. Several members were identified with good hNav1.7 potency and excellent rat pharmacokinetic profiles. Compound 4 had good efficacy (52% and 41% reversal of allodynia at 2 and 4 h post-dose, respectively) in the Chung rat spinal nerve ligation (SNL) model of neuropathic pain when dosed orally at 10 mg/kg.
- London, Clare,Hoyt, Scott B.,Parsons, William H.,Williams, Brande S.,Warren, Vivien A.,Tschirret-Guth, Richard,Smith, McHardy M.,Priest, Birgit T.,McGowan, Erin,Martin, William J.,Lyons, Kathryn A.,Li, Xiaohua,Karanam, Bindhu V.,Jochnowitz, Nina,Garcia, Maria L.,Felix, John P.,Dean, Brian,Abbadie, Catherine,Kaczorowski, Gregory J.,Duffy, Joseph L.
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p. 1696 - 1701
(2008/12/23)
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- Synthesis of 2-azastilbene derivatives with intramolecular charge transfer
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The condensation reaction of 2-cyanomethyl-5-nitropyridine with aromatic aldehydes has been carried out with the aim of preparing 2-azastilbene derivatives having intramolecular charge transfer. The yield of the condensation products can be increased if the reaction is carried out in the medium used for obtaining the starting 2-cyanomethyl-5-nitropyridine without separating or purifying it. The electronic absorption spectra of the compounds show a charge-transfer band, the energy of which increases and the intensity falls with lowering of the electron-donor properties of the substituent in the 4-position. Introduction of the heteroatom into the acceptor part when changing from the stilbene to the 2-azastilbene system is accompanied by a decrease in the energy and increase in the intensity of the charge-transfer electronic transition.
- Kokars,Yanishevskii,Kampars
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p. 805 - 809
(2007/10/03)
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- The oxidative amination of 3-nitropyridines
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3-Nitropyridine was reacted with ammonia or alkylamines and KMnO4 under several different conditions. Substitutions in the para position to the nitro group were obtained with high regioselectivity: with ammonia, 2-amino-5-nitropyridine (66%), w
- Bakke, Jan M,Svensen, Harald
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p. 4393 - 4395
(2007/10/03)
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- Regioselectivity of the Amination of Some 3-Nitropyridines by Liquid Ammonia / Potassium Permanganate
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3-Nitropyridine and some of its derivatives are aminated in a liquid ammonia solution of potassium permanganate to the corresponding 2- and (or) 4- and (or) 6-amino compounds.Quantumchemical calculations for a few 3-nitropyridines suggest that the experimentally observed regioselectivity of the amination is controlled by Coulombic interaction. --- Key Words: Amination / Nitropyridines / Reactivity indices / Calculations, MNDO
- Wozniak, Marian,Baranski, Andrzej,Szpakiewicz, Barbara
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p. 875 - 878
(2007/10/02)
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- Alkaline Hydrolysis of N-Methyl-2,4-dinitroacetanilide and N-Alkyl-N-(5-nitro-2-pyridyl)acetamides
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The kinetics of the alkaline hydrolysis of N-methyl-2,4-dinitroacetanilide (2), N-ethyl- (3), and N-methyl-N-(5-nitro-2-pyridyl)acetamide (4) was carried out.The reaction path consists of two stages: the first one is the rate-limiting formation of the first tetrahedral intermediate (monoanionic) and the second one the fast decomposition of the intermediate.The latter fast decomposition of the intermediate (monoanionic) involves two processes: one is the direct decomposition of the intermediate to the products and the other is a proton abstraction of the hydroxyl group of the intermediate by -OH giving the second tetrahedral intermediate (dianionic), followed by its deconposition to the products.For the alkaline hydrolysis of 2-4, the decomposition of the first intermediate occurred predominantly via the latter process.
- Kijima, Atsushi,Sekiguchi, Shizen
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p. 3597 - 3602
(2007/10/02)
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- Synthesis of 2-Amino-3-nitropyridines and -1,4-dihydropyridines
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The title compounds 4 and 5 can be synthesized from the primary nitroketene aminal 2 and 1,3-biselectrophiles like β-aminoketones (ketonic Mannich bases) or enaminoketones.
- Mertens, Hubert,Troschuetz, Reinhard,Roth, Hermann J.
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p. 380 - 383
(2007/10/02)
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- Process for the synthesis of intermediates in the preparation of diaminopyridines
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The present invention relates to a process for preparing aminonitropyridines comprising reacting an alkoxynitropyridine with ammonium acetate.
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- SYNTHESES WITH AROMATIC NITRAMINES, V. PHOTOCHEMICAL REARRANGEMENT OF NITRAMINOPYRIDINES
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All three isomeric nitraminopyridines were photolysed in methanol with low-pressure mercury lamp (253.7 nm). 2-Nitraminopyridine yielded both 2-amino-3-nitro- and 2-amino-5-nitropyridines (isomer ratio 6.26 : 1). 3-Nitropyridine rearranged into both 4-nitro- and 2-nitro-3-aminopyridines (isomer ratio 1.28 : 1), whereas 4-nitraminopyridine gave 3-nitro-4-aminopyridine as the sole product. 1-Methyl-2-nitriminopyridine did not rearrange under the conditions applied, but 1-methyl-4-nitriminopyridine gave 3-nitro-4-methylaminopyridine.The latest product was also obtained when the same starting material was rearranged in conc. sulfuric acid.
- Sepiol, J.,Tomasik, P.
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p. 159 - 164
(2007/10/02)
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- Kinetic Studies of the Mechanism of the Nitraminopyridine Rearrangement
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Rate data are reported for the rearrangement, in 92percent sulfuric acid at 30 deg C, of a series of 4-X-2-nitraminopyridines (X=H, Me, Br, Cl, MeO, CO2H) and of 4-methyl-2-nitramino(3-D)-pyridine.Values of pKa for second protonation of the corresponding pyridin-2-amines were also measured and rate constants for nitration of the monoprotonated pyridinamines were thereby calculated.The results suggest that the rate-determining step occurs prior to formation of the appropriate 3- and 5-nitro ? complexes.The nature of this step is not clear, however, and a key role for the nitramine itself is not proven by the current evidence
- Deady, Leslie W.,Korytsky, Olga L.
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p. 2035 - 2040
(2007/10/02)
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- Chemotherapeutically effective nitro compounds. III. Nitropyridines, nitroimidazopyridines and related compounds
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New 2 nitropyridines and 3 nitropyridines, and 3 nitroimidazo [1,2 a] pyridines and related compounds (together 106) were synthesized and tested for their chemotherapeutic efficacy against trichomonads, amoebas and other organisms, such as Eimeria tenella, bacteria, fungi and helminths. Several 2 nitropyridines revealed a detectable systemic effect against Entamoeba histolytica (extraintestinal amoebiasis of the golden hamster) and also a weak activity against Trichomonas fetus in the NMRI mouse. Only a few 3 nitropyridines showed a marked systemic effect against trichomonads. Of the 3 nitroimidazo [1,2 a] pyridines, only the electroneutral carboxylic acid amide group exhibited a pronounced activity, exclusively against trichomonads; however, the activity was nullified by electronegative, electropositive and other electroneutral substituents. As they were not superior in chemotherapeutic respect compared to the known standard preparations (metronidazole), no further tests were carried out with the most effective compounds.
- Winkelmann,Raether,Hartung,Wagner
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