Category: 138786-86-4

Related Products of 138786-86-4, The chemical industry reduces the impact on the environment during synthesis 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

Example 12 Benzyl-(2S)-4-(5-{[(4-amino-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)-2-methylpiperazine-1-carboxylate A solution of methyl 4-nitro-1H-pyrazole-3-carboxylate (54.0 g, 315.6 mmol), phenylboronic acid (77.0 g, 631.2 mmol), copper(II) acetate (86.0 g, 473.4 mmol) and pyridine (49.9 g, 631.2 mmol) in methylene chloride (600 mL) was stirred at ambient temperature open to air for 48 hours. The reaction was evaporated in vacuo, diluted with 1 L of methylene chloride and filtered through a large plug of silica (washing with 2 L methylene chloride). The solvent was evaporated in vacuo to give methyl 4-nitro-1-phenyl-1H-pyrazole-3-carboxylate confirmed by 1H NMR (CDCl3) delta 8.61 (s, 1H), 7.73 (m, 2H), 7.50 (m, 3H), 4.02 (s, 3H).

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, Methyl 4-nitro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hamblett, Christopher; Mampreian, Dawn M.; Methot, Joey L.; Miller, Thomas; Sloman, David L.; Stanton, Matthew G.; Wilson, Kevin; US2009/105264; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 138786-86-4, name is Methyl 4-nitro-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 138786-86-4, name: Methyl 4-nitro-1H-pyrazole-3-carboxylate

Reference Example 39 Methyl 4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylate To a solution (275 mL) of methyl 4-nitro-1H-pyrazole-3-carboxylate obtained in Reference Example 1 (27.4 g, 160 mmol) and p-toluenesulfonic acid monohydrate (3.04 g, 16 mmol) in chloroform, 2,3-dihydropyran (19.0 mL, 330 mmol) was added at 0 C., and the mixture was warmed to room temperature, and stirred for 3 hr. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 2:1) to give the title compound (34.8 g, yield 85%) as pale-yellow oily substance. 1H-NMR (CDCl3): delta 1.62-1.77 (3H, m), 1.83-2.04 (2H, m), 2.15-2.27 (1H, m), 3.68-3.76 (1H, m), 3.99 (3H, s), 4.03-4.13 (1H, m), 5.43 (1H, dd, J=2.7 Hz, 9.1 Hz), 8.38 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-nitro-1H-pyrazole-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 138786-86-4

PART I: Synthesis Scheme I, shows that 4-nitro-1H-pyrazole-3-carboxylic acid (compound 12) was alkylated with methyl iodide in the presence of potassium carbonate in DMF. After flash chromatography on silica gel, two regioisomers, alkyl 1-alkyl-4-nitro-1H-pyrazole-3-carboxylate (compound 13a, 1,3-isomer) and alkyl 1-alkyl-4-nitro-1H-pyrazole-5-carboxylate (compound 13b, 1,5-isomer) were obtained in 26% and 74% yield, respectively. The structures of the isomers (compounds 13a, 13b) were determined by NOESY analysis: a NOESY correlation was observed between H-5 and alkyl protons in compound 13a.16 The nitro group of compounds 13a and 13b was reduced by hydrogenation in the presence of a catalytic amount of catalytic amount of 10% Pd/C to produce amines compounds 14a and 14b, respectively. Cyclization of compound 14b with urea afforded compound 15. Chlorination of compound 15 with POCl3 and DIPEA in toluene afforded compound 16 in 68% yield. Treatment with appropriate substituted anilines in isopropanol with 1 drop of conc. HCl with compound 16, provided the instant compounds 4-11 of this invention (65-78% yields).

The synthetic route of 138786-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duquesne University of the Holy Spirit; Gangjee, Aleem; (26 pag.)US2019/276457; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 138786-86-4, name is Methyl 4-nitro-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 138786-86-4, Safety of Methyl 4-nitro-1H-pyrazole-3-carboxylate

Reference Example 27 Methyl 4-nitro-1-trityl-1H-pyrazole-3-carboxylate To a solution of methyl 4-nitro-1H-pyrazole-3-carboxylate obtained in Reference Example 18 (5.0 g, 29.0 mmol) and triethylamine (4.5 mL, 32.0 mmol) in DMF (50 mL), trityl chloride (8.9 g, 32.0 mmol) was added at 0 C., and the mixture was stirred at room temperature for 4 hr. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 9:1) to give the title compound (7.3 g, yield 61%). 1H-NMR (CDCl3): delta 3.28 (3H, s), 7.14-7.19 (5H, m), 7.30-7.35 (10H, m), 8.11 (1H, s).

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, Methyl 4-nitro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 138786-86-4,Some common heterocyclic compound, 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, molecular formula is C5H5N3O4, 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.

To a solution of 4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (3.1 g, 18.1 mmol) in dry acetone (2 ml) was added K2C03 (5 g, 36.2 mmol) at 25C. The reaction mixture was cooled to 0C, and methyl iodide (2.2 ml, 36.3 mmol) was added. The temperature was again raised to 25C, and then heated to 70C for 2 hrs. The solvent was removed in vacuo The residue was diluted with EtOA and washed with water and with brine, dried (Na2S04), filtered, and concentrated. The crude product was purified by column chromatography over silica gel. Elution with 20% EtOAc/hexane) gave the undesired isomer 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid methyl ester (1 g, 30%), subsequent elution with 40% EtOAc/hexane provided the desired isomer l-methyl-4-nitro-lH-pyrazole-3-carboxylic acid methyl ester (1.8 g, 54%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-nitro-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; GRUBER, Felix; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; WO2011/154327; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 138786-86-4, These common heterocyclic compound, 138786-86-4, name is Methyl 4-nitro-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.

PART I: Synthesis Scheme I, shows that 4-nitro-1H-pyrazole-3-carboxylic acid (compound 12) was alkylated with methyl iodide in the presence of potassium carbonate in DMF. After flash chromatography on silica gel, two regioisomers, alkyl 1-alkyl-4-nitro-1H-pyrazole-3-carboxylate (compound 13a, 1,3-isomer) and alkyl 1-alkyl-4-nitro-1H-pyrazole-5-carboxylate (compound 13b, 1,5-isomer) were obtained in 26% and 74% yield, respectively. The structures of the isomers (compounds 13a, 13b) were determined by NOESY analysis: a NOESY correlation was observed between H-5 and alkyl protons in compound 13a.16 The nitro group of compounds 13a and 13b was reduced by hydrogenation in the presence of a catalytic amount of catalytic amount of 10% Pd/C to produce amines compounds 14a and 14b, respectively. Cyclization of compound 14b with urea afforded compound 15. Chlorination of compound 15 with POCl3 and DIPEA in toluene afforded compound 16 in 68% yield. Treatment with appropriate substituted anilines in isopropanol with 1 drop of conc. HCl with compound 16, provided the instant compounds 4-11 of this invention (65-78% yields).

The synthetic route of 138786-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duquesne University of the Holy Spirit; Gangjee, Aleem; (26 pag.)US2019/276457; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 138786-86-4 as follows. Application In Synthesis of Methyl 4-nitro-1H-pyrazole-3-carboxylate

Preparation of tert-Butyl (3-Amino-1-phenyl-1H-pyrazol-4-yl)carbamate (I); A solution of methyl 4-nitro-1H-pyrazole-3-carboxylate (54.0 g, 315.6 mmol), phenylboronic acid (77.0 g, 631.2 mmol), copper(II) acetate (86.0 g, 473.4 mmol) and pyridine (49.9 g, 631.2 mmol) in methylene chloride (600 mL) was stirred at ambient temperature open to air for 48 hours. The reaction was evaporated in vacuo, diluted with 1000 mL methylene chloride and filtered through a large plug of silica (washing with 2 liters methylene chloride). The solvent was evaporated in vacuo. 1H NMR (CDCl3) delta 8.61 (s, 1H), 7.73 (m, 2H), 7.50 (m, 3H), 4.02 (s, 3H).

According to the analysis of related databases, 138786-86-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Berk, Scott C.; Close, Joshua; Hamblett, Christopher; Heidebrecht, Richard W.; Kattar, Solomon D.; Kliman, Laura T.; Mampreian, Dawn M.; Methot, Joey L.; Miller, Thomas; Sloman, David L.; Stanton, Matthew G.; Tempest, Paul; Zabierek, Anna A.; US2007/117824; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-nitro-1H-pyrazole-3-carboxylate

Compound 6 and 6A: To a mixture containing 5 (3.1 g, 18.1 mmol) and potassium carbonate (5.0 g, 36.2 mmol) in 60 mL of acetone was added methyl iodide (2.2 mL, 36.2 mmol). The resulting solution was heated and stirred at 70 C. for 2 hours. After the reaction mixture was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate (×3). The combined organics were washed with brine, dried (MgSO4), and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel using 20% ethyl acetate in hexanes as the eluent to afford 6 (1.1 g, 33%) as white solid. 1H NMR (d6-DMSO) delta 3.96 (s, 3H) 3.98 (s, 3H) 8.36 (s, 1H); ES (+) MS m/e=186 (M+1) and using 30% ethyl acetate in hexanes to afford 6A (2.2 g, 66%) as white solid. 1H NMR (d-CDCl3) delta 3.98 (s, 3H) 4.00 (s, 3H) 8.13 (s, 1H); ES (+) MS m/e=186 (M+1).

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.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2007/27166; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, 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. Formula: C5H5N3O4

Preparative Example 7 4-nitro-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester 340 mg (1.99 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.33 ml (2.19 mM) of iodomethane and 1.3 g (3.98 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 195 mg (53%) of the title compound and 110 mg (30%) of the compound of Preparative Example 13. 1H NMR (300 MHz, CDCl3) delta 4.00 (s, 3H), 4.02 (s, 3H), 8.15 (s, 1H). Mass: 185 (M+) ; 340 mg (1.99 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.33 ml (2.19 mM) of iodomethane and 1.3 g (3.98 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 110 mg (30%) of the title compound and 195 mg (53%) of the compound of Preparative Example 7.1H NMR (300 MHz, CDCl3) delta 4.03 (s, 3H), 4.04 (s, 3H), 8.03 (s, 1H).

The synthetic route of 138786-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; US2010/63106; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-nitro-1H-pyrazole-3-carboxylate

Reference Example 20 Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate A mixture of methyl 4-nitro-1H-pyrazole-3-carboxylate obtained in Reference Example 18 (2.0 g, 11.7 mmol), methyl iodide (2.0 g, 14.0 mmol), potassium carbonate (1.62 g, 11.7 mmol) and acetone (60 mL) was stirred at 30 C. for 5 hr. The mixture was diluted with water, and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 4:1-1:1) to give the title compound, methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate (Rf value 0.43) (0.95 g, yield 44%) and the title compound, methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate (Rf value 0.71) (0.61 g, yield 28%).

The synthetic route of 138786-86-4 has been constantly updated, and we look forward to future research findings.