15366-34-4 | Page 7 of 9 | pyrazoles-derivatives

Kiselyov, Alexander S.’s team published research in Bioorganic & Medicinal Chemistry Letters in 2007 | CAS: 15366-34-4

Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4) belongs to pyrazoles. The application of pyrazole derivatives in the development of anticancer agents has been thoroughly investigated and verified. Moreover, the medicinal features of a number of natural products incorporating pyrazole moiety such as pyrazofurin, pyrazofurin B, pyrazole-3(5)-carboxylic acid and 4-methylpyrazole-3(5)-carboxylic acid have been reported.Synthetic Route of C5H6N2O2

In 2007,Kiselyov, Alexander S.; Milligan, Daniel; Ouyang, Xiaohu published 《Novel inhibitors of VEGF receptors-1 and -2 based on azole-5-carboxamide templates》.Bioorganic & Medicinal Chemistry Letters published the findings.Synthetic Route of C5H6N2O2 The information in the text is summarized as follows:

We have developed a series of novel potent 1-(2-(pyridin-4-yl)ethyl)-1H-azole-5-carboxamides active against kinases VEGFR-2 and -1. Both specific and dual ATP-competitive inhibitors of VEGFR-2 were identified. Kinase selectivity could be controlled by varying the 5-carboxamide substituent at the azole ring. The most specific mols. displayed >10-fold selectivity for VEGFR-2 over VEGFR-1. Compound activities in vitro and in cell-based assays (IC50 < 100 nM) were similar to those of reported clin. and development candidates, including PTK787 (Vatalanibtrade) and ZD6474 (Vandetanib). High permeability of active compounds across the Caco-2 cell monolayer (>40×10-5 cm/min) is indicative of their potential for intestinal absorption upon oral administration. In the part of experimental materials, we found many familiar compounds, such as Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Synthetic Route of C5H6N2O2)

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

Juanes, Olga’s team published research in Journal of the Chemical Society, Chemical Communications in 1985 | CAS: 15366-34-4

In 1985,Juanes, Olga; De Mendoza, Javier; Rodriguez-Ubis, Juan Carlos published 《Synthesis of macrobicyclic ligands containing pyrazole subunits: the N,N’-bipyrazolyl cryptand》.Journal of the Chemical Society, Chemical Communications published the findings.Recommanded Product: 15366-34-4 The information in the text is summarized as follows:

The cryptands I and II were prepared in 19 and 56% yield, resp., by reaction of 3,3′-bis(bromomethyl)-1,1′-bipyrazole with anhydrous NH3 and 4,13-diaza-1,7,10,16-tetraoxacyclooctadecane, resp., in dry MeCN at 100°. The tripodal pyrazolyl ligands III (R = H, Me, CH2Ph) were prepared analogously in 35, 41, and 39% yield, resp., by reaction of the appropriate pyrazoles IV with anhydrous NH3. After reading the article, we found that the author used Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Recommanded Product: 15366-34-4)

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

Danagulyan, Gevorg G.’s team published research in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2015 | CAS: 15366-34-4

Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4) belongs to pyrazoles. Pyrazole derivatives have been reported to exhibit a wide range of applications in medicinal chemistry and pharmacology. A large number of drugs incorporating pyrazole structure have been utilized as partial agonists for nicotinic acid receptors, antidepressants, antimicrobial agents, antiviral agents, and antifungal agents solely or along with the combination of other structural motifs.Electric Literature of C5H6N2O2

Electric Literature of C5H6N2O2In 2015 ,《Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts》 appeared in Chemistry of Heterocyclic Compounds (New York, NY, United States). The author of the article were Danagulyan, Gevorg G.; Tumanyan, Araksya K.; Attaryan, Oganes S.; Tamazyan, Rafael A.; Danagulyan, Anna G.; Ayvazyan, Armen G.. The article conveys some information:

The authors studied a reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of N-azolyl- and C-pyrazole-substituted carboxylic acids, which were synthesized from the resp. esters and hydrazine hydrate. This reaction was shown to result in recyclization and formation of Et 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-a]pyrimidine. The synthesis of the target compounds was achieved using 2-(2-ethoxy-2-oxoethyl)-1,4,6-trimethylpyrimidinium iodide and 1H-pyrazole-3-carboxylic acid hydrazide, 1H-pyrazole-1-acetic acid hydrazide, 1H-1,2,4-triazole-1-acetic acid hydrazide as key reactants. The title compounds thus formed included (pyrazolyl)pyrazolo[1,5-a]pyrimidine derivatives and (triazolyl)pyrazolo[1,5-a]pyrimidine derivatives In the part of experimental materials, we found many familiar compounds, such as Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Electric Literature of C5H6N2O2)

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

Randow, Hendrik’s team published research in Wissenschaftliche Zeitschrift der Universitaet Rostock, Naturwissenschaftliche Reihe in 1990 | CAS: 15366-34-4

In 1990,Randow, Hendrik; Miethchen, Ralf published 《Regioselectivity in N-alkylations of pyrazoles and 1,2,4-triazoles》.Wissenschaftliche Zeitschrift der Universitaet Rostock, Naturwissenschaftliche Reihe published the findings.Product Details of 15366-34-4 The information in the text is summarized as follows:

The regioselectivity of the N-alkylation of pyrazoles I (R1 = H, Me, Br, Cl, iodo; R2 = H, Br, iodo; R3 = Me, CO2Me, Br, iodo) and the triazoles II (R4 = Br, Cl) with BrCH2COOMe and, in some cases, MeI is discussed with the help of product NMR data. The experimental process involved the reaction of Methyl 1H-pyrazole-3-carboxylate(cas: 15366-34-4Product Details of 15366-34-4)

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

Brief introduction of 15366-34-4

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1H-pyrazole-3-carboxylate, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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 15366-34-4, Recommanded Product: 15366-34-4

c) Methyl l-cyclopropyl-lH-pyrazole-3-carboxylateMethyl lH-pyrazole-3-carboxylate (4 g, 31.7 mmol) was dissolved in di- chloroethane (160 ml). Na2C03 (6.72 g, 63.4 mmol) and cyclopropylboronic acid (5.44 g, 63.4 mmol) were added to the solution. The resulting mixture was heated to 70 C and a hot solution of bipyridine (4.92 g, 31.6 mmol) and Cu(OAc)2 (5.72 g, 31.6 mmol) in dichloroethane (40 ml) was added. The mixture was stirred at 70 C under an oxygen atmosphere overnight. Saturated aqueous solution of NaHC03 was added to the reaction mixture and extracted with EtOAc. The organic layer was evaporated and the residue was purified by flash chromatography. Yield 2.5 g. – NMR (400 MHz; DMSO-d6): delta 1.04-1.09 (m, 2H), 1.17-1.23 (m, 2H), 3.64-3.69 (m, IH), 3.91 (s, 3H), 6.78 (d, IH), 7.46 (d, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1H-pyrazole-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Simple exploration of Methyl 1H-pyrazole-3-carboxylate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1H-pyrazole-3-carboxylate, its application will become more common.

Reference of 15366-34-4,Some common heterocyclic compound, 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, molecular formula is C5H6N2O2, 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.

1 -Chloro-4-iodo-benzene (3.5 g, 14.7 mmol), methyl 1 H-pyrazole-3-carboxylate (1.85 g, 14.7 mmol) and Cul (0.235 g, 1.47 mmol), L-proline (0.405 g, 2.94 mmol), K2C03 (4.1 g, 29.4 mmol) in DMSO (40ml_) were stirred at 90 C for10 hours. The reaction mixture was filtered and the organic layer was diluted with EtOAc (300 ml_), washed with brine (100 ml. x 3), and dried over Na2S04. Evaporation of the solution on a water bath under reduced pressure gave methyl 1 -(4-chlorophenyl)pyrazole-3-carboxylate (2.3 g, 66% yield).

Reference:
Patent; BASF SE; WINTER, Christian; RHEINHEIMER, Joachim; WOLF, Antje; TERTERYAN, Violeta; POONOTH, Manojkumar; WIEBE, Christine; KREMZOW-GRAW, Doris; ROeHL, Franz; ROHRER, Sebastian Georgios; WIEJA, Andy; ROSENBAUM, Claudia; GRAMMENOS, Wassilios; WO2014/202703; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some tips on C5H6N2O2

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 15366-34-4

To a mixture of tert-butyl 3-(methanesulfonyloxy)azetidine-l-carboxylate (750 mg, 2.98 mmol) in DMF (10 mL) was added K2C03(1.2 g, 8.95 mmol) and methyl lH-pyrazole- 3-carboxylate (376.4 mg, 2.98 mmol). The reaction was stirred at 100 C overnight. TLC showed the reaction was complete. The mixture was washed with water and extracted with EA. The organic layer was dried over anhydrous Na2S04and concentrated under reduced pressure to give methyl l-(l-(tert-butoxycarbonyl)azetidin-3-yl)-lH-pyrazole-3-carboxylate (650 mg). LC-MS (ESI) found: 236 [M+H-56]+.

Reference:
Patent; ZAFGEN, INC.; ZAHLER, Robert; VATH, James, E.; (239 pag.)WO2019/118612; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Sources of common compounds: 15366-34-4

The synthetic route of 15366-34-4 has been constantly updated, and we look forward to future research findings.

Electric Literature of 15366-34-4, These common heterocyclic compound, 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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.

A 50 mL flask was charged with 1.89 g of startingmaterial 1 (15mmol), 1.96 g of starting material 2 (10 mmol),400 mg of Cul (2.0 mmol), 4.5 gofK 2C 0 3 (3.3 mmol) and 0.9mL of trans-N,N’-dimethylcyclohexayldiamine (2.0 mmol).The resulting mixture was stirred at 140 C. for 3 h. After themixture was cooled down to room temperature, 200 mL ofEtOAc was added and the oiganics were washed with water(2×50 mL), brine (2×50 mL). The oiganics were dried overM gS04 and concentrated under reduced pressure. The residuewas purified via flash chromatography on silica gel(0-25% EtOAc in hexanes) to get the desired product 3 (1.2 g,50%).

The synthetic route of 15366-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Continuously updated synthesis method about Methyl 1H-pyrazole-3-carboxylate

According to the analysis of related databases, 15366-34-4, the application of this compound in the production field has become more and more popular.

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 15366-34-4 as follows. Recommanded Product: 15366-34-4

A solution of methyl 1H-pyrazole-3-carboxylate (5 g) in dry acetonitrile was treated with cesium carbonate (32.3 g) and methyl iodide (6.45 g) and the mixture was stirred at rt for 2 h. The suspension was filtered and the volatiles were removed under reduced pressure. The residue was purified by chromatography (SiO2, Cy/EtOAc) to yield the desired product (66% yield). LC-MS (Method 1): m/z [M+H]+=141.2 (MW calc.=140.14); Rt=1.0 min.

According to the analysis of related databases, 15366-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194443; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

A new synthetic route of Methyl 1H-pyrazole-3-carboxylate

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.