Category: pyrazoles-derivatives

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 26621-44-3 as follows. name: 3-Nitro-1H-pyrazole

3-Nitropyrazole (11.3 g, 0.1 mol) at room temperature,Benzyl bromide (17.1 g, 0.1 mol), tetrabutylammonium bromide (1.6 g, 0.005 mol), dissolved in 10 ml of dimethyl sulfoxide (DMSO).Add sodium hydroxide solution [sodium hydroxide solution: 8.8 g (0.22 mol)The solution obtained by dissolving sodium hydroxide in 10 ml of water], the reaction is exothermic,After the dropwise addition is completed, the mixture is stirred at room temperature overnight, and diluted with water to quench.Extract with dichloromethane, dry, concentrate and recrystallize with semi-dry petroleum ether.The product was obtained in 18.3 g with a yield of 90%.

According to the analysis of related databases, 26621-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (16 pag.)CN108863936; (2018); A;,
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 3112-31-0 as follows. Product Details of 3112-31-0

To a 25 mL reactor, 174.0 mg of 3,5-pyrazoledicarboxylic acid monohydrate and 250.0 mg of copper sulfate pentahydrate powder were added, 5 mL of pyridine and 10 mL of water were added, and after stirring for 15 minutes, the reaction kettle was placed in an oven and heated to 180. °C, reaction for 24 hours; After the reaction is completed, the reaction solution is transferred to a flask, and 2 mL of a saturated aqueous solution of sodium sulfide is added to the reaction solution, and after the precipitation is completed, it is filtered:Add 1M hydrochloric acid solution to the filtrate droplet obtained in the second step, adjust the solution pH=3, and filter;The filtrate obtained in the third step was extracted with an organic solvent dichloromethane (3×20 mL), and the organic phase was collected and dried over anhydrous sodium sulfate for 10 h;The organic phase obtained after the fourth step of drying was concentrated and dried to obtain 100 mg of a white powder, which was designated as sample 1.

According to the analysis of related databases, 3112-31-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Fujian Structure Of Matter Institute; Huang Deguang; Xiang Shiqun; Zhang Xiaofeng; (13 pag.)CN109369617; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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).

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:
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

These common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, 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. COA of Formula: C3H5N3

Neat 1 H-pyrazol-4-amine (55.2 mg, 0.66 mmol) was added in one charge to a stirred solution of 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method D; 170 mg, 0.55 mmol), EDC (318 mg, 1.66 mmol) and HOBT (254 mg, 1.66 mmol) in N,N-dimethylformamide (4 ml) in air at room temperature. The reaction mixture was stirred at room temperature overnight. Water (30 ml) was added, and the mixture was extracted with ethyl acetate (50 ml x 2). The organic layers were combined, dried over MgSO,,, and concentrated in vacuo. The residue was washed with ethyl acetate yield the title compound as a brown solid. 180 mg.1HNMR (400 MHz, DMSO-c/6): 5.26 (s, 2H), 7.24 (d, 1 H), 7.35-7.45 (m, 4H), 7.52 (d, 2H), 7.65-7.68 (m, 1 H), 7.77 (d, 1 H), 7.93 (s, 1 H), 10.21 (s, 1 H), 12.66 (s, 1 H).MS (electrospray): m/z [M+H]+ = 372

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

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

400877-57-8, name is Methyl 1-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. Computed Properties of C6H7N3O4

10% palladium/C (2.87 g, 2.7 mmol) was added to a stirred solution of methyl 1 -methyl- 4-nitro-1 H-pyrazole-3-carboxylate (p69, 7.15 g, 38.6 mmol) in methanol (250 ml_) and stirred at RT under H2 atmosphere for 4 hrs. The catalyst was filtered off and the solvent was evaporated under vacuum to afford methyl 4-amino-1 -methyl-1 H-pyrazole- 3-carboxylate (p70, 6 g, y= quant) as purple wax used as such in the next step. MS (/T7/z): 156.1 [MH]+

The synthetic route of 400877-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; CREMONESI, Susanna; SEMERARO, Teresa; TARSI, Luca; GIBSON, Karl Richard; (116 pag.)WO2019/81939; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1453-58-3, A common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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 suspension of hexane washed potassium hydride (0.424 g) in dimethylformamide (5 ml) was treated in one portion with 3-methyl pyrazole (0.85 ml) while stirring. After the gas evolution ceased, 2-chloro-4-fluorobenzoic acid methyl ester (2.0 g, 10.6) was added to the clear solution and heated at 130° C. for 15 minutes. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and brine. The organic phase was washed with water, brine,. and dried over anhydrous sodium sulfate. Removal of solvent in vacuo afforded 2.2 g of a yellow oil. (Note: 20percent hydrolysis of the ester was detected by analysis of the NMR spectrum of the crude product). The desired regioisomer 2-chloro-4-(3-methyl-1H-pyrazol-1-yl)-benzoic acid methyl ester was isolated from the other isomer (described below) by flash column chromatography on silica gel (Merck 60) eluting with dichloromethane-hexane 2:1) to give 1.55 g of the title compound as a colorless solid. MS (EI m/z: 250/252 (M)+. [00283] The 5-regioisomer, namely 2-chloro-4-(5-methyl-1H-pyrazol-1-yl)-benzoic acid methyl ester was isolated from the above flash column chromatography on silica gel (Merck 60) by further eluting with dichloromethane-hexane 2:1 to give 0.20 g of the product as a colorless solid. MS (EI), m/z: 250/252 (M)+.

The synthetic route of 1453-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6831079; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 stirred solution of /erf-butyl 2,6^hydropyrrolo[3,4-c]pyrazole-5(4 /)- carboxylate (20 g, 96 mmol) in DMF (200 mL) at 0 C was added sodium hydride (4.21 g, 105 mmol). After stirring for 1 h at RT, 2-trimetbylsilylethoxymethyl chloride (SEM-C1) (4.65 mL, 26.3 mmol) was added. The resulting mixture was stirred at RT overnight. The mixture was quenched with saturated NuEta4OmicronEta, and the solvents were removed. The residue was diluted with ethyl acetate (500 mL), washed with water, brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on a silica gel Biotage 65i column, eluting with 0 to 20% ethyl acetate in hexanes to give the title compound as a colorless gum. LC-MS: 340.1 (Mu+Eta)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HICKS, Jacqueline, D.; BIFTU, Tesfaye; CHEN, Ping; QIAN, Xiaoxia; WILKENING, Robert, R.; WO2011/146358; (2011); 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. 25016-17-5, name is Methyl 5-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

b. Synthesis of I.S-dimethyl-pyrazole-delta-carboxylic acid methylester; S-methyl-pyrazole-delta-carboxylic acid methyl ester (6.8 Kg Kg) is dissolved in DMF (8L) and dimethyl sulfate (6.0 L) is added dropwise in over three hours. The reaction is exothermic and the addition of dimethyl sulfate must be controlled so that the internal temperature does not exceed 900C. After complete addition, the mixture is heated for 18 hours at 800C. The mixture is then cooled to room temperature, diluted with ice (3.4 Kg), and cooled in an ice bath. A solution of aqueous 28% ammonium hydroxide (8.6 L) is added to the reaction mixture over 3 hours. The resulting mixture is stirred for 18 hours, diluted with ethyl acetate (12 L) and water (16 L), extracted, and the layers are separated. The organic layer is washed with water (4L), dried over MgSO4, filtered, and concentrated under reduced pressure to provide 5.14 Kg of 1 ,3-dimethyl-pyrazole-delta-carboxylic acid methylester (69 % yield with a purity of >90 % by HPLC). The crude product is used directly in the next step.

The synthetic route of 25016-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2006/48761; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1151802-23-1, name is 4-Bromo-1-cyclopropyl-1H-pyrazole, 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 1151802-23-1, Application In Synthesis of 4-Bromo-1-cyclopropyl-1H-pyrazole

Step 1 : l-Cyclopropyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyridaziiie To a 100 n L flask is added 4-bromo-l-cyclopropylpyrazol (6.57 g, 35.1 mmol) and anhydrous THF (30 niL). The solution is cooled to -78 C under nitrogen; then n-butyl lithium (15.5 n L, 2.5 M in hexanes, 38.6 mmol) is added dropwise. The reaction mixture is stirred at the temperature for 1 hr, followed by addition of isopropyl boronate (9.17 g, 94.1 mmol) and stirred below -70 C for 3 hours. The reaction is quenched with water (20 n L) and the resulted mixture is adjusted to pH 8-9 with aqueous hydrochloride solution (1 N). The combined organic phases are concentrated and used in next step without further purification (6.64 g, 81% yield). (MS: [M+l] 235)

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.

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHONG, Boyu; SHIH, Chuan; YUAN, Hongbin; ZHOU, Feng; WO2014/32498; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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