- Simple synthesis process of ethyl 5-methyl-1H-pyrazole-3-formate
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The invention discloses a simple synthesis process of ethyl 5-methyl-1H-pyrazole-3-formate, which comprises the following steps: by using diethyl oxalate and acetone as main raw materials, ethanol asa solvent and sodium ethoxide as alkali, carrying out condensation reaction to prepare an intermediate, and carrying out cyclization on the intermediate and hydrazine hydrate under an acidic conditionto synthesize ethyl 5-methyl-1H-pyrazole-3-formate. The whole process has the advantages of simple and accessible raw materials, simple and feasible operation and favorable economic benefit.
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Paragraph 0015-0017
(2021/02/24)
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- Synthesis process of lapatinib intermediate ethyl 1, 5-dimethyl-1H-pyrazole-3-formate
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The invention relates to a synthesis process of a lapatinib intermediate ethyl 1, 5-dimethyl-1H-pyrazole-3-formate, which comprises the following steps: 1, making diethyl oxalate react with acetone togenerate an intermediate product, and 2, making the intermediate product prepared in the step 1 react with methylhydrazine to generate the ethyl 1, 5-dimethyl-1H-pyrazole-3-formate. Diethyl oxalate and acetone are used as main raw materials, and a target product is synthesized through condensation and cyclization reactions. Particularly, during the second-step cyclization reaction, the conversionrate of the product is effectively increased, the content of impurities is inhibited, and the purity and yield of the product are improved by controlling the temperature, the feeding sequence and thepH value of the reaction solution.
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Paragraph 0010; 0012
(2021/02/24)
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- Synthesis method of 1, 3-dimethyl-1H-pyrazole-5-ethyl formate
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The invention relates to a synthesis method of 1, 3-dimethyl-1H-pyrazole-5-ethyl formate. The synthesis method comprises the following steps: 1. mixing ethanol, sodium ethoxide and diethyl oxalate, dropwisely adding acetone into the reaction solution reversely and slowly, keeping the internal temperature at 15 DEG C or below, and carrying out heat-preservation reaction for 24 hours to obtain an intermediate; 2, mixing DMF and the intermediate obtained in the step 1, cooling the reaction solution to 5-15 DEG C, slowly dropwise adding methylhydrazine into the reaction solution, and maintaining the internal temperature to be below 15 DEG C; after dropping, heating to 40-50 DEG C, and keeping the temperature to react for 6 hours; adding a reaction solution; concentrating under reduced pressureto obtain a crude product; and further carrying out reduced pressure distillation on the crude product to prepare the 1, 3-dimethyl-1H-pyrazole-5-ethyl formate. The method is simple and easy to obtain, reaction is easy to control, and aftertreatment is simple. By controlling the temperature and the feeding sequence, the conversion rate of the product is effectively increased, the content of impurities is inhibited, and the purity and the yield of the product are improved.
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Paragraph 0009-0010
(2021/01/30)
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- PYRAZINE DERIVATIVE
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Provided is a novel pyrazine derivative represented by the following formula (I) or a pharmaceutically acceptable salt thereof, or a solvate thereof which is useful for treating or preventing diseases in which URAT1 is involved, including gout, hyperurice
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Paragraph 0085
(2017/04/04)
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- Facile synthesis of 1,2,3-tricarbonyls from 1,3-dicarbonyls mediated by cerium(IV) ammonium nitrate
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A mild and efficient protocol for the synthesis of vicinal tricarbonyl compounds from β-dicarbonyls in a single step using cerium(IV) ammonium nitrate as a catalytic oxidant is described. Ease of execution, wide substrate scope and the suitability for the synthesis of commercially important compounds like ninhydrin, alloxan and oxoline make this reaction particularly noteworthy.
- Sivan, Akhil,Deepthi, Ani
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supporting information
p. 1890 - 1893
(2014/03/21)
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- Discovery of cell-active phenyl-imidazole Pin1 inhibitors by structure-guided fragment evolution
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Pin1 is an emerging oncology target strongly implicated in Ras and ErbB2-mediated tumourigenesis. Pin1 isomerizes bonds linking phospho-serine/threonine moieties to proline enabling it to play a key role in proline-directed kinase signalling. Here we report a novel series of Pin1 inhibitors based on a phenyl imidazole acid core that contains sub-μM inhibitors. Compounds have been identified that block prostate cancer cell growth under conditions where Pin1 is essential.
- Potter, Andrew,Oldfield, Victoria,Nunns, Claire,Fromont, Christophe,Ray, Stuart,Northfield, Christopher J.,Bryant, Christopher J.,Scrace, Simon F.,Robinson, David,Matossova, Natalia,Baker, Lisa,Dokurno, Pawel,Surgenor, Allan E.,Davis, Ben,Richardson, Christine M.,Murray, James B.,Moore, Jonathan D.
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scheme or table
p. 6483 - 6488
(2010/12/18)
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- Intramolecular inverse-electron-demand Diels-Alder reactions of imidazoles with 1,2,4-triazines: A new route to 1,2,3,4-tetrahydro-1,5-naphthyridines and related heterocycles
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The intramolecular inverse-electron-demand Diels-Alder reaction between imidazoles and 1,2,4-triazines linked by a trimethylene tether from the imidazole N1 position to the triazine C3 proceed in excellent yields to produce 1,2,3,4-tetrahydro-1,5-naphthyridines. The reaction proceeds by a cycloaddition with subsequent loss of nitrogen, followed by a presumed stepwise loss of a nitrile. The analogous intramolecular cycloadditions employing a tetramethylene tether also proceeded to give 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines in acceptable yields. The reaction to produce the tetrahydro-1,5-naphthyridines can also be promoted with microwave irradiation.
- Lahue, Brian R.,Lo, Sie-Mun,Wan, Zhao-Kui,Woo, Grace H. C.,Snyder, John K.
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p. 7171 - 7182
(2007/10/03)
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- DIKETOACID-DERIVATIVES AS INHIBITORS OF POLYMERASES
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Diketoacids of Formula (A) are useful as inhibitors of viral polymerases. In particular hepatitis C virus RNA dependent RNA polymerase (HCV RdRp), hepatitis B virus polymerase (HBV pol) and reverse transcriptase of human immunodeficiency virus (HIV RN.) The group R may be broadly chosen and is an organic moiety which contains 2 to 24 carbon atoms and includes an optionally cyclic or heterocyclic group in which the atom directly bonded to the adjacent carbonyl in the diketoacid is part of the ring structure
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- Synthesis and Chemistry of Acyltriazolinedione Ylides and Related Intermediates: New Methods for the Preparation of Di- and Tricarbonyl Compounds
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α-Urazolylcarbonyl compounds can be easily oxidized to the corresponding ylides, and these ylides hydrolyzed to the corresponding carbonyl compounds.In addition these same urazole precursors can be converted to carbonyl compounds via a novel version of the Swern oxidation.These two methods not only are of synthetic value in the preparation of 1,2-dicarbonyl and 1,2,3-tricarbonyl compounds but also serve as useful probes for the formation of triazolinedione ylides and the related urazolium species.
- Wilson, R. Marshall,Hengge, Alvan C.
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p. 197 - 202
(2007/10/02)
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- Indole as a Dienophile in Inverse Electron Demand Diels-Alder Reactions: Reactions with 1,2,4-Triazines and 1,2-Diazines
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Indole reacts with 1,2,4-triazines in the absence of solvent or in the presence of limited amounts of solvent to produce β- or γ-carbolines, benzonaphthyridines, or the noncyclized 3-indoles.The combined yields of cycloadducts with tricarbalkoxytriazines exceeds 90 percent, with the production of γ-carbolines exceeding 80 percent.The regiochemistry of the adduct and the ratio of the products is determined mainly by electronic effects of the triazine substituents.Indole also ungergoes a cyclocondensation reaction with tetramethyl 1,2-diazine-3,4,5,6-tetracarboxylate to give trimethyl 5H-6-oxophenanthridine-2,3,4-tricarboxylate.
- Benson, Scott C.,Gross, Jonathan L.,Snyder, John K.
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p. 3257 - 3269
(2007/10/02)
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- Synthesis of 2-oxy> 3-Keto Esters from 3-Keto Esters and (p-Nitrophenyl)sulfonyl Peroxide
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The preparation of 2-oxy> β-keto esters from β-keto esters and (p-nitrophenyl)sulfonyl peroxide is described.High yields are obtained for a variety of structural types.One β-diketone was also used and gave comparable success.Thes
- Hoffman, Robert V.,Wilson, Anna Lee,Kim, Hwa-Ok
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p. 1267 - 1270
(2007/10/02)
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- 2-(((p-Nitrophenyl)sulfonyl)oxy)-3-keto Esters: Versatile Intermediates for the Preparation of 1,2,3-Tricarbonyl Compounds
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The excellent leaving ability of the nosylate group and the high, differentiated functional group density in 2-(((p-nitrophenyl)sulfonyl)oxy)-3-keto esters, 1, suggested that they might serve as versatile precursors for the synthesis of other 1,2,3-trifunctionalized compounds.Reaction of 2-(nosyloxy)-3-keto esters with triethylamine gives 1,2,3-tricarbonyl compounds in high yields.The tricarbonyl compound can be reacted, without isolation, with nucleophiles to give heterocyclic products in excellent yields.
- Hoffman, Robert V.,Kim, Hwa-Ok,Wilson, Anna Lee
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p. 2820 - 2822
(2007/10/02)
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- THE USE OF NITRATE ESTERS IN THE SYNTHESIS OF DI- AND TRI-CARBONYL COMPOUNDS
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Vicinal di- and tri-carbonyl compounds are prepared by reacting some electrophiles, bearing a C=O vicinal to the leaving group, with an anion exchanger, in the nitrate form, or with the ammonium salt n-Bu4N(+)NO3(-).
- Cainelli, Gianfranco,Manescalchi, Francesco,Plessi, Laura
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p. 163 - 164
(2007/10/02)
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- Heterocycles from α-Nitroolefins, VIII. - 2-Methyl-3-pyrrolecarboxylates from α-Nitroolefins and Acetoacetates
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3-Pyrrolecarboxylates 4 can be prepared from α-nitroolefins 1 and acetoacetates 2 by two methods: (a) 1 and 2 react to give 4,5-dihydro-5-methyleneamino-3-furancarboxylates 3 which are hydrolyzed, (b) the nitronic acids 8, adducts of 1 and 2, yield with different reduction agents the heterocycles 4.
- Boberg, Friedrich,Garburg, Karl-Heinz,Goerlich, Karl-Joachim,Pipereit, Eberhard,Ruhr, Maria
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p. 239 - 250
(2007/10/02)
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- A SIMPLE ACCESS TO α,β-DIKETOESTERS
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Carboxylic acid chlorides react with 1,2-diethoxy-1,2-bis(trimethylsilyloxy)ethylene in the presence of catalytic amounts of ZnCl2 to produce regiospecifically protected α,β-diketoesters.
- Reetz, M. T.,Kyung, Suk-Hun
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p. 6333 - 6336
(2007/10/02)
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- Kinetics of Oxidation of Ethyl Acetoacetate by Selenium Dioxide
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The title reaction in aqueous acetic acid medium is first order each in and .Presence of mineral acid catalyses the reaction rate.Primary salt effect is negligible.Increase in percentage of acetic acid in the reaction medium increases the reaction rate.A suitable mechanism has been suggested.
- Valechha, N. D.,Pradhan, Asha
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p. 773 - 774
(2007/10/02)
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