37622-90-5 | Page 10 of 16 | pyrazoles-derivatives

Fotsing, Joseph R. team published research on Journal of Medicinal Chemistry in 2020 | 37622-90-5

37622-90-5, Ethyl 4-pyrazolecarboxylate, also known as Ethyl pyrazole-4-carboxylate, is a useful research compound. Its molecular formula is C6H8N2O2 and its molecular weight is 140.14 g/mol. The purity is usually 95%.

Ethyl pyrazole-4-carboxylate is a low yield, transition metal salt that is used in the synthesis of pyrazoles. It can be synthesized by the reaction of sodium ethoxide with ethyl chloroformate and a Grignard reagent. Sodium ethoxide is added to a suspension of sodium chloride and dried ethyl chloroformate, followed by addition of magnesium turnings. The mixture is refluxed for one hour, cooled, and filtered to give crystals. Ethyl pyrazole-4-carboxylate is used in the preparation of ethyl esters from aliphatic alcohols by reacting with boron trichloride or phosphorus pentachloride. It participates in certain chemical reactions as a byproduct and can damage equipment during chemical reactions. The yield of this compound can be increased by using an excess amount of Grignard reagent or adding hexamethylenetetramine to the reaction mixture, Recommanded Product: Ethyl 4-pyrazolecarboxylate

Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. 37622-90-5, formula is C6H8N2O2, Name is Ethyl 4-pyrazolecarboxylate. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. Recommanded Product: Ethyl 4-pyrazolecarboxylate.

Fotsing, Joseph R.;Darmohusodo, Vincent;Patron, Andrew P.;Ching, Brett W.;Brady, Thomas;Arellano, Melissa;Chen, Qing;Davis, Timothy J.;Liu, Hanghui;Servant, Guy;Zhang, Lan;Williams, Mark;Saganich, Michael;Ditschun, Tanya;Tachdjian, Catherine;Karanewsky, Donald S. research published 《 Discovery and Development of S6821 and S7958 as Potent TAS2R8 Antagonists》, the research content is summarized as follows. In humans, bitter taste is mediated by 25 TAS2Rs. Many compounds, including certain active pharmaceutical ingredients, excipients, and nutraceuticals, impart their bitter taste (or in part) through TAS2R8 activation. However, effective TAS2R8 blockers that can either suppress or reduce the bitterness of these compounds have not been described. We are hereby reporting a series of novel 3-(pyrazol-4-yl) imidazolidine-2,4-diones as potent and selective TAS2R8 antagonists. In human sensory tests, S6821(I) and S7958(II), two of the most potent analogs from the series, demonstrated efficacy in blocking TAS2R8-mediated bitterness and were selected for development. Following data evaluation by expert panels of a number of national and multinational regulatory bodies, including the US, the EU, and Japan, S6821 and S7958 were approved as safe under conditions of intended use as bitter taste blockers.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Desai, Shrey P. team published research on Organic Letters in 2021 | 37622-90-5

Synthetic Route of 37622-90-5, Ethyl 4-pyrazolecarboxylate, also known as Ethyl pyrazole-4-carboxylate, is a useful research compound. Its molecular formula is C6H8N2O2 and its molecular weight is 140.14 g/mol. The purity is usually 95%.

Desai, Shrey P.;Taylor, Mark S. research published 《 Diarylborinic Acid-Catalyzed Regioselective Ring Openings of Epoxy Alcohols with Pyrazoles, Imidazoles, Triazoles, and Other Nitrogen Heterocycles》, the research content is summarized as follows. A method for regioselective ring openings of 3,4- and 2,3-epoxy alcs. with ambident nitrogen heterocycles is described. Using a diarylborinic acid catalyst, a single regioisomer is favored in couplings of nucleophile and electrophile partners that display low regioselectivity under conventional conditions. The method provides access to aromatic heterocycles bearing stereochem. defined, functionalized alkyl substituents, a product class similar in structure to medicinally relevant compounds such as the acyclic nucleoside analogs.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Cho, Jong hyun team published research on Tetrahedron Letters in 2015 | 37622-90-5

Application In Synthesis of 37622-90-5, Ethyl 4-pyrazolecarboxylate, also known as Ethyl pyrazole-4-carboxylate, is a useful research compound. Its molecular formula is C6H8N2O2 and its molecular weight is 140.14 g/mol. The purity is usually 95%.

Cho, Jong hyun;Coats, Steven J.;Schinazi, Raymond F. research published 《 Synthesis of carbocyclic nucleoside analogs with five-membered heterocyclic nucleobases》, the research content is summarized as follows. New carbocyclic nucleoside analogs with five-membered heterocyclic nucleobases were synthesized and evaluated as potential anti-HIV and anti-HCV agents. Among the synthesized carbocyclic nucleoside analogs, the pyrazole amide 15f exhibited modest selective anti-HIV-1 activity (EC₅₀ = 24 μM).

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Collibee, Scott E. team published research on Journal of Medicinal Chemistry in 2021 | 37622-90-5

Name: Ethyl 4-pyrazolecarboxylate, Ethyl 4-pyrazolecarboxylate, also known as Ethyl pyrazole-4-carboxylate, is a useful research compound. Its molecular formula is C6H8N2O2 and its molecular weight is 140.14 g/mol. The purity is usually 95%.

Pyrazoles are synthesized by the reaction of α,β-unsaturated aldehydes with hydrazine and subsequent dehydrogenation. 37622-90-5, formula is C6H8N2O2, Name is Ethyl 4-pyrazolecarboxylate. Substituted pyrazoles are prepared by condensation of 1,3-diketones with hydrazine (Knorr-type reactions). For example, acetylacetone and hydrazine gives 3,5-dimethylpyrazole. Name: Ethyl 4-pyrazolecarboxylate.

Collibee, Scott E.;Bergnes, Gustave;Chuang, Chihyuan;Ashcraft, Luke;Gardina, Jeffrey;Garard, Marc;Jamison, Chris R.;Lu, Kevin;Lu, Pu-Ping;Muci, Alexander;Romero, Antonio;Valkevich, Ellen;Wang, Wenyue;Warrington, Jeffrey;Yao, Bing;Durham, Nickie;Hartman, James;Marquez, Anna;Hinken, Aaron;Schaletzky, Julia;Xu, Donghong;Hwee, Darren T.;Morgans, David;Malik, Fady I.;Morgan, Bradley P. research published 《 Discovery of Reldesemtiv, a Fast Skeletal Muscle Troponin Activator for the Treatment of Impaired Muscle Function》, the research content is summarized as follows. Herein, the discovery of reldesemtiv I, a second-generation fast skeletal muscle troponin activator (FSTA) that increases force production at submaximal stimulation frequencies, is reported. Property-based optimization of high throughput screening hit, 4-(4-fluorobenzyl)-5-(phenethylamino)-1,2,4-thiadiazole, led to compounds with improved free exposure and in vivo muscle activation potency compared to the first-generation FSTA, tirasemtiv. The compound I demonstrated increased muscle force generation in a phase 1 clin. trial and is currently being evaluated in clin. trials for the treatment of amyotrophic lateral sclerosis.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Corbin, Daniel A. team published research on ChemCatChem in | 37622-90-5

Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns. 37622-90-5, formula is C6H8N2O2, Name is Ethyl 4-pyrazolecarboxylate. 1-Methyl-5-(trifluoromethyl)pyrazole underwent deprotonation and subsequent carboxylation mainly or exclusively at either the 4-position of the heterocycle or at the nitrogen-attached methyl group. Application In Synthesis of 37622-90-5.

Corbin, Daniel A.;Cremer, Christopher;Puffer, Katherine O.;Newell, Brian S.;Patureau, Frederic W.;Miyake, Garret M. research published 《 Effects of the Chalcogenide Identity in N-Aryl Phenochalcogenazine Photoredox Catalysts》, the research content is summarized as follows. Phenochalcogenazines such as phenoxazines and phenothiazines were widely employed as photoredox catalysts (PCs) in small mol. and polymer synthesis. However, the effect of the chalcogenide in these catalysts was not fully studied. Four phenochalcogenazines is synthesized to understand how the chalcogenide impacts catalyst properties and performance. Increasing the size of the chalcogenide is found to distort the PC structure, ultimately impacting the properties of each PC. For example, larger chalcogenides destabilize the PC radical cation, possibly resulting in catalyst degradation PCs with larger chalcogenides experience increased reorganization during electron transfer, leading to slower electron transfer. Ultimately, catalyst performance is evaluated in organocatalyzed atom transfer radical polymerization and a photooxidation reaction for C(sp²)-N coupling. Results from these experiments highlight that a balance of PC properties is most beneficial for catalysis, including a long-lived excited state, a stable radical cation, and a low reorganization energy.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Dallinger, Doris team published research on Journal of Organic Chemistry in 2016 | 37622-90-5

Product Details of C6H8N2O2, Ethyl 4-pyrazolecarboxylate, also known as Ethyl pyrazole-4-carboxylate, is a useful research compound. Its molecular formula is C6H8N2O2 and its molecular weight is 140.14 g/mol. The purity is usually 95%.

Dallinger, Doris;Pinho, Vagner D.;Gutmann, Bernhard;Kappe, C. Oliver research published 《 Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane》, the research content is summarized as follows. A configurationally simple and robust semibatch apparatus for the in situ on-demand generation of anhydrous solutions of diazomethane (CH₂N₂) avoiding distillation methods is presented. Diazomethane is produced by base-mediated decomposition of com. available Diazald within a semipermeable Teflon AF-2400 tubing and subsequently selectively separated from the tubing into a solvent- and substrate-filled flask (tube-in-flask reactor). Reactions with CH₂N₂ can therefore be performed directly in the flask without dangerous and labor-intensive purification operations or exposure of the operator to CH₂N₂. The reactor has been employed for the methylation of carboxylic acids, the synthesis of α-chloro ketones and pyrazoles, and palladium-catalyzed cyclopropanation reactions on laboratory scale. The implementation of in-line FTIR technol. allowed monitoring of the CH₂N₂ generation and its consumption. In addition, larger scales (1.8 g diazomethane per h) could be obtained via parallelization (numbering up) by simply wrapping several membrane tubings into the flask.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

9/23/2021 News The important role of 37622-90-5

The synthetic route of 37622-90-5 has been constantly updated, and we look forward to future research findings.

37622-90-5, name is Ethyl 4-pyrazolecarboxylate, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of Ethyl 4-pyrazolecarboxylate

Ethyl 1-(4-(hydroxymethyl)benzyl)-1H-pyrazole-4-carboxylate Combined ethyl 1H-pyrazole-4-carboxylate (2.31 g; 16.48 mmol; 1.00 eq.), [4-(chloromethyl)phenyl]methanol (2.58 g; 16.48 mmol; 1.00 eq.), DMAP (0.04 g; 0.33 mmol; 0.02 eq.), and potassium carbonate (4.55 g; 32.97 mmol; 2.00 eq.) in acetonitrile (30.00 ml). Heated the reaction to 90 C. for 2 hours. Let the reaction cool to rt. Diluted reaction with water, extracted with ethyl acetate, combined organics, dried with MgSO4, filtered, and concentrated. The residue was purified by silica gel column to give ethyl 1-(4-(hydroxymethyl)benzyl)-1H-pyrazole-4-carboxylate (3.7 g, 86%)1H NMR (400 MHz, Chloroform-d) delta 7.93 (d, J=0.7 Hz, 1H), 7.84 (d, J=0.7 Hz, 1H), 7.40-7.34 (d, J=6.2 Hz, 2H), 7.24 (d, J=6.2 Hz, 2H), 5.29 (s, 2H), 4.70 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 1.36-1.29 (m, 3H).

The synthetic route of 37622-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

September 17, 2021 News Analyzing the synthesis route of 37622-90-5

Statistics shows that Ethyl 4-pyrazolecarboxylate is playing an increasingly important role. we look forward to future research findings about 37622-90-5.

Synthetic Route of 37622-90-5, These common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Reference Example 1 ethyl 3,5-dibromo-1H-pyrazole-4-carboxylate (0885) (0886) To a mixed solution of ethyl 1H-pyrazole-4-carboxylate (31.0 g), sodium acetate (118 g), ethanol (200 mL) and water (300 mL) was added bromine (141 g), and the mixture was stirred at room temperature for 10 hr. To the reaction mixture was added sodium thiosulfate (175 g), and the solvent was evaporated under reduced pressure. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (65.1 g). MS (ESI+): [M+H]+ 296.7

Statistics shows that Ethyl 4-pyrazolecarboxylate is playing an increasingly important role. we look forward to future research findings about 37622-90-5.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

9/13/2021 News New learning discoveries about 37622-90-5

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-pyrazolecarboxylate, and friends who are interested can also refer to it.

Reference of 37622-90-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 37622-90-5 name is Ethyl 4-pyrazolecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 8 -(4-Chloromethyl-benzyl)-1 H-pyrazole-4-carboxylic acid ethyl ester 1 H-Pyrazole-4-carboxylic acid ethyl ester (2 g, 13.9 mmol), (4-chloromethyl-phenyl)- methanol (2.21 g, 13.9 mmol) and triphenylphosphine (4.49 g, 16.8 mmol) are dissolved in tetrahydrofuran (40 ml). The solution is cooled to 0C then diethylazodicarboxylate(6.47 ml, 16.6 mmol) is added. The mixture is stirred at 0C for 2 hours, then 1 hour at room temperature. The solvent is removed under vacuum and the residue is purified by flash chromatography (0 – 50% ethyl acetate in cyclohexane) to give the title compound (Yield 1 .72 g). LC (Method 2): tR = 4.40 min; Mass spectrum (ES+): m/z = 279 [M+H ]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-pyrazolecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; BAKKER, Remko; GIOVANNINI, Riccardo; HAMPRECHT, Dieter; LINGARD, Iain; PAUTSCH, Alexander; WELLENZOHN, Bernd; (92 pag.)WO2017/72020; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

9/9/2021 News Introduction of a new synthetic route about 37622-90-5

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 4-pyrazolecarboxylate, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 37622-90-5, Product Details of 37622-90-5

To a solution of NaH (1.08 g, 25.70 mmol) in THF (30 mL) at ambient temperature under nitrogen atmosphere was added a solution of ethyl 1H-pyrazole-4-carboxylate (3.00 g, 21.41 mmol) in THF (10 mL) and stirring was continued for I h. Then benzyl bromide (3.06 mL, 25.7 mmol) was added over the period of 15 mm and the reaction was stirred for 22 h. Thereaction mixture was cooled to 10 C diluted with aqueous NH4CI (100 mL) and extracted with ethyl acetate (2 x 80 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Redisep-120 g, 0-30% EtOAc/n-Hexane) to obtain Intermediate 45A (450 g, 88%) as a white solid. 1H NMR. (400 MHz, 1)MSO-d6) 6 ppm 1.23 – 1 .28 (m, 3 H),4.21 (q. J:::: 719 Hz, 2 H), 537 (s, 2 H), 7.25 – 738 (in, 5 H), 787 (s, 1 H), 8.46 (s, 1 H). LCMS Method-H): retention time 1.8 mm, [M±H] 2310.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics