37687-24-4 | Page 2 of 4 | pyrazoles-derivatives

Simple exploration of Diethyl 3,5-pyrazoledicarboxylate

The synthetic route of Diethyl 3,5-pyrazoledicarboxylate has been constantly updated, and we look forward to future research findings.

Electric Literature of 37687-24-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (3.00 g, 14.1 mmol), 2-bromo-1-[3-methyl-4-(trifluoromethyl)phenyl]ethanone (Intermediate 188A, 4.37 g, 15.5 mmol) and potassium carbo- nate (2.15 g, 15.5 mmol) in acetone (40 ml) was stirred at RT overnight. After filtering off the sol- ids, the filtrate was evaporated and the residue partitioned between dichloromethane and water. The organic phase was washed with water and brine, then dried over sodium sulfate and evapo- rated to give the title compound (5.70 g, 81 % of theory, 83% purity). LC/MS [Method 6]: Rt = 1.29 min; MS (ESIpos): m/z = 413 [M+H]+. 1H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.11 (s, 1H), 8.04 (d, 1H), 7.90 (d, 1H), 7.36 (s, 1H), 6.30 (s, 2H), 4.31 (q, 2H), 4.20 (q, 2H), 2.55 (s, 3H), 1.31 (t, 3H), 1.19 (t, 3H). 19F-NMR (376 MHz, DMSO-d6): d [ppm] = -60.95 (s, 3F).

The synthetic route of Diethyl 3,5-pyrazoledicarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; MUeLLER, Steffen; SCHOHE-LOOP, Rudolf; ORTEGA, HERNANDEZ, Nuria; SUeSSMEIER, Frank; JIMENEZ NUNEZ, Eloisa; BRUMBY, Thomas; LINDNER, Niels; GERDES, Christoph; POOK, Elisabeth; BUCHMUeLLER, Anja; GAUGAZ, Fabienne, Zdenka; LANG, Dieter; ZIMMERMANN, Stefanie; EHRMANN, Alexander, Helmut, Michael; GERISCH, Michael; LEHMANN, Lutz; TIMMERMANN, Andreas; SCHAeFER, Martina; SCHMIDT, Georg; SCHLEMMER, Karl-Heinz; FOLLMANN, Markus; KERSTEN, Elisabeth; WANG, Vivian; GAO, Xiang; WANG, Yafeng; (801 pag.)WO2019/219517; (2019); A1;,
Pyrazole – Wikipedia,
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A new synthetic route of 37687-24-4

According to the analysis of related databases, 37687-24-4, the application of this compound in the production field has become more and more popular.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 37687-24-4

A solution of 849 mg (4.00 mmol) diethyl pyrazole-3,5-dicarboxylate and 1.02 g (4.00 mmol) 2-bromo-1-(4-tert-butyl-phenyl)-ethanone in 4 ml acetone is treated with 663 mg (4.80 mmol) potassium carbonate. The resulting suspension is stirred overnight at room temperature. The reaction mixture is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated to give 1-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-1H-pyrazole-3,5-dicarboxylic acid diethyl ester as light yellow foam; HPLC/MS 2.77 (A), [M+H] 387.

According to the analysis of related databases, 37687-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; DORSCH, Dieter; BUCHSTALLER, Hans-Peter; MOINET, Gerard; WEGENER, Ansgar; WO2013/143663; (2013); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Extracurricular laboratory: Synthetic route of Diethyl 3,5-pyrazoledicarboxylate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 3,5-pyrazoledicarboxylate, its application will become more common.

Application of 37687-24-4,Some common heterocyclic compound, 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, molecular formula is C9H12N2O4, 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.

Preparation of Intermediate 1-12.A mixture of Intermediate 1-13 (1.21 g, 2.65 mmol), diethyl 3,5- pyrazoledicarboxylate (539 mg, 2.54 mmol) and K2C03 (440 mg, 3.18 mmol) in acetone (20 mL) was stirred overnight at rt. Water (50 mL) was added and the mixture was extracted with DCM (4 x 150 mL). The combined organic layers were washed with brine (50 mL), dried (MgS04), filtered and evaporated. The residue was purified by column chromatography (EtOAc:cyclohexane, 30:70) and the product obtained was triturated from Et20 to give the desired product (898 mg, 66%) as a white solid.1H N R (300 MHz, DMSO) delta 9.02 (s, 2H), 7.34 (s, 1 H), 7.22 (d, J = 8.6 Hz, 4H), 6.89 (d, J = 8.7 Hz, 4H), 6.14 (s, 2H), 4.83 (s, 4H), 4.31 (q, J = 7.1 Hz, 2H), 4.23 (q, J = 7.1 Hz, 2H), 3.73 (s, 6H), 1.31 (t, J = 7.1 Hz, 3H), 1.22 (t, J = 7.1 Hz, 3H).

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALES, Sonia; RODRIGUEZ HERGUETA, Antonio; RAMOS LIMA, Francisco, Javier; ALVAREZ ESCOBAR, Rosa, Maria; HIGUERAS HERNANDEZ, Ana Isabel; WO2011/141713; (2011); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Analyzing the synthesis route of C9H12N2O4

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, Diethyl 3,5-pyrazoledicarboxylate, other downstream synthetic routes, hurry up and to see.

Electric Literature of 37687-24-4, The chemical industry reduces the impact on the environment during synthesis 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, I believe this compound will play a more active role in future production and life.

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (5.95 g, 28.0 mmol), 2-bromo-1-(2,3-dihydro-1H-inden-5-yl)ethan-1-one (Intermediate 129A, 9.57 g, 70% purity, 28.0 mmol) and potassium carbonate (9.68 g, 70.1 mmol) in acetone (250 ml) was stirred at RT overnight. Then, the mixture was filtered, and the filtrate was concentrated to afford the crude product which was used in the next step without further purification. Yield: 10.4 g (65% of theory, 65% purity). LC/MS [Method 7]: Rt = 1.15 min; MS (ESIpos): m/z = 371 [M+H]+.

Introduction of a new synthetic route about Diethyl 3,5-pyrazoledicarboxylate

According to the analysis of related databases, 37687-24-4, the application of this compound in the production field has become more and more popular.

Example 4: ethyl 4-hydroxy-6-methyl-pyrazolo[l,5-a]pyrazine-2-carboxylate (0257) l-Chloropropan-2-one (10.5 kg, 113 mol) was added slowly at room temperature (0258) (exothermic) to a suspension of diethyl lH-pyrazole-3,5-dicarboxylate (20 kg, 94.2 mol) and cesium carbonate (30.7 kg, 94.2 mol) in acetone (200 1). The reaction mixture was stirred for 1.5 hours, filtred and the precipitate was washed with acetone. Acetone was distilled off from the filtrate at 60 C to obain a volume of 60-90 1, DMSO (85 1) was added and the distillation was continued until acetone was completely removed. (0259) Ammonium acetate (14.5 kg, 188 mol) was added at room temperature. The reaction mixture was stirred at 80 C for 18 hours, cooled to 60 C and water (290 1) was slowly added. The suspension was stirred 2 hours at 0-5 C. The precipitate was filtered off, washed with water and dried at 70 C under high vacuum affording ethyl 4-hydroxy-6- methyl-pyrazolo[l,5-a]pyrazine-2-carboxylate (16.8 kg, 80.6%) as beige crystals. (0260) 1H-NMR (600 MHz, DMSO-d6): 11.51 (s, 1H), 7.62 (s, 1H), 7.32 (s, 1H), 4.33 (q, 2H), 2.14 (s, 3H), 1.32 (t, 3H); MS(ISP): m/e = 222.09 (M+H+).

According to the analysis of related databases, 37687-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DOTT, Pascal; FEYEN, Fabian; HILDBRAND, Stefan; HOFFMANN, Ursula; HOFFMANN-EMERY, Fabienne; MEIER, Roland; MOINE, Gerard; REGE, Pankaj; WUITSCHIK, Georg; (64 pag.)WO2017/186668; (2017); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Share a compound : 37687-24-4

Adding a certain compound to certain chemical reactions, such as: 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, 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 37687-24-4, COA of Formula: C9H12N2O4

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (2.00 g, 9.42 mmol), 2-bromo-1-(3,4-dihydro-2/-/-chromen-2-yl)ethanone (Intermediate 209A, 2.52 g, 9.90 mmol) and potassium carbonate (1.43 g, 10.4 mmol) in dry acetone (50 ml) was stirred at RT overnight. After filtering off the solids, the filtrate was evaporated and the residue partitioned between dichloromethane and water. The organic phase was washed with water and brine, then dried over sodium sulfate and concen- trated. The residue was purified by flash-chromatography on silica gel (80 g, eluent: 0-25% ethyl acetate in petroleum ether) to give the title compound (2.88 g, 79% of theory). 1H-NMR (300 MHz, CDCIs): d [ppm] = 7.44 (s, 1H), 7.21-7.16 (m, 1H), 7.12-7.10 (m, 1H), 6.95- 6.90 (m, 2H), 5.95 (d, 1H), 5.69 (d, 1H), 4.75-4.71 (m, 1H), 4.42 (q, 2H), 4.30 (q, 2H), 2.88-2.82 (m, 2H), 2.36-2.17 (m, 2H), 1.40 (t, 3H), 1.35 (t, 3H).

Extended knowledge of 37687-24-4

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 3,5-pyrazoledicarboxylate, and friends who are interested can also refer to it.

In 250 mL of acetonitrile was dissolved 2-chloro-1-(i-methyl-1H- pyrazol-4-yl)ethanone (18.3 g, 115 mmol) and diethyl iH-pyrazole-3,5-dicarboxylate (24.5 g, 115 mmol) before finely ground K2C03 (31.9 g, 231 mmol) was added in one portion. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was filtered and the cake was washed with acetonitrile (100 mL). The filtrate was concentrated in vacuo to a thick oil. The oil was dissolved in EtOAc (80 mL), and heptane (200 mL) was added slowly with stirring. The resultant solids were stirred for 2 hours, then filtered and washed with heptane. The solids were dried in a vacuum oven to afford diethyl 1-(2-(i-methyl-1H-pyrazol-4- yl)-2-oxoethyl)-1H-pyrazole-3,5-dicarboxylate (26.4 g, 77.4 mmol, 67.1 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 3,5-pyrazoledicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The important role of Diethyl 3,5-pyrazoledicarboxylate

Synthetic Route of 37687-24-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (3.00 g, 14.1 mmol), 2-bromo-1-(8-fluoronaph- thalen-2-yl)ethanone (Intermediate 205A, 3.78 g, 14.1 mmol) and potassium carbonate (2.15 g, 15.6 mmol) in acetone (40 ml) was stirred at RT overnight. After filtering off the solids, the filtrate was evaporated and the residue partitioned between dichloromethane and water. The organic phase was washed with water and brine, then dried over sodium sulfate and concentrated. The crude product was purified by flash-chromatography on silica gel (80 g, eluent: 0-20% ethyl ace- tate in petroleum ether) to give the title compound (4.21 g, 70% of theory, 94% purity). LC/MS [Method 6]: Rt = 1.25 min; MS (ESIpos): m/z = 399 [M+H]+. 1H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.85 (s, 1H), 8.22 (d, 1H), 8.14-8.10 (m, 1H), 7.94 (d, 1H), 7.77-7.72 (m, 1H), 7.55-7.50 (m, 1H), 7.39 (s, 1H), 6.46 (s, 2H), 4.33 (q, 2H), 4.24 (q, 2H), 1.32 (t, 3H), 1.18 (t, 3H).

Introduction of a new synthetic route about 37687-24-4

The synthetic route of 37687-24-4 has been constantly updated, and we look forward to future research findings.

In 250 mL of acetonitrile was dissolved 2-chloro-l-(l -methyl- 1H- pyrazol-4-yl)ethanone (18.3 g, 115 mmol) and diethyl lH-pyrazole-3,5-dicarboxylate (24.5 g, 115 mmol) before finely ground K2CO3 (31.9 g, 231 mmol) was added in one portion. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was filtered, and the cake was washed with acetonitrile (100 mL). The filtrate was concentrated in vacuo to a thick oil. The oil was dissolved in EtOAc (80 mL), and heptane (200 mL) was added slowly with stirring. The resultant solids were stirred for 2 h, then filtered and washed with heptane. The solids were dried in a vacuum oven to afford the title compound (26.4 g, 67% yield).

The synthetic route of 37687-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Sources of common compounds: Diethyl 3,5-pyrazoledicarboxylate

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. 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 37687-24-4

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (5.20 g, 24.5 mmol), 2-chloro-1-(3-chloro-4-methylphenyl)ethan-1-one (4.98 g, 24.5 mmol), potassium carbonate (3.73 g, 27.0 mmol) and water (3 drops) in acetone (100 ml) was stirred at RT overnight. The solids were then filtered off, and the filtrate was concentrated under reduced pressure. The residue was partitioned between dichloromethane and water. The layers were separated, and the organic layer was washed with water and brine, dried over sodium sulfate and filtered. The filtrate was concentrated under re- duced pressure to afford the crude title compound which was directly used in the next step with- out further purification. Yield: 7.99 g (83% of theory, 97% purity). LC/MS [Method 34]: Rt = 1.39 min; MS (ESIpos): m/z = 379/381 [M+H]+.