Category: pyrazoles-derivatives

Related Products of 37622-90-5, 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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

l-(Chloromethyl)-4-methoxybenzene (157 mmol, 24.5 g) and K2CO3 (39.43 g, 285.71 mmol) were added to a solution of ethyl lH-pyrazole-4- carboxylate (143 mmol, 20.0 g) in acetonitrile (150 mL). The resulting mixture was stirred under reflux for 5 h. After cooling to rt, the mixture was filtered and concentrated in vacuum. The residue was purified by flash chromatography over silica gel using EtOAc/PE ( 1 :20 to -1 :5) as eluent to afford ethyl l-(4-methoxybenzyl)-lH- pyrazole-4-carboxylate ( 126.7 mmol, 33 g, 89%) as an off-white solid. LC-MS: m/z ES = 261.

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

Reference:
Patent; ADDEX PHARMA S.A.; BOLEA, Christelle; CELANIRE, Sylvain; BOUDOU, Cedric; TANG, Lam; ROCHER, Jean-Philippe; LIVERTON, Nigel, J.; WO2012/9009; (2012); A2;,
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. 360056-45-7, name is Methyl 4-amino-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H7N3O2

2,6-dichlorobenzoyl chloride (8.2 g; 39.05 mmol) was added cautiously to a solution of 4- amino-1H-pyrazole-3-carboxylic acid methyl ester (prepared in a manner analogous to 165B) (5 g; 35.5 mmol) and triethylamine (5.95 ml; 42.6 mmol) in dioxan (50 ml) then stirred at room temperature for 5 hours. The reaction mixture was filtered and the filtrate treated with methanol (50 ml) and 2M sodium hydroxide solution (100 ml), heated at 50 0C for 4 hours, and then evaporated. 100 ml of water was added to the residue then acidified with concentrated hydrochloric acid. The solid was collected by filtration, washed with water (100 ml) and sucked dry to give 10.05 g of 4-(2,6-dichloro-benzoylamino)-1H- pyrazole-3-carboxylic acid as a pale violet solid.

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; ASTEX THERAPEUTICS LIMITED; WO2008/1101; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 1572-10-7, name is 3-Amino-5-phenylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Amino-5-phenylpyrazole

A mixture of 2,6-Dichloro-4-(piperidine-l-sulfonyl)-pyridine (190 mg, 0.644 mmol), 3-amino-5-phenylpyrazole (113 mg, 0.708 mmol) and DIPEA (249 mg, 1.93 mmol) in anhydrous DMSO (2 mL) was heated at 140 C for 16h. The mixture was partitioned between EtOAc (50 mL) and water (15 mL) and the phases separated. The organic phase was washed with water (2 x 5 mL), brine (5 mL), dried (Na2S04), filtered and concentrated in vacuo. The crude material was purified by flash chromatography, eluting with EtOAc (50 %) in heptane + to afford the title compound as a brown solid (65 mg, 15%) MS: m/z = 418.1 (M+H) .

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1572-10-7.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); 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 1203705-55-8 as follows. Safety of 3-Bromo-1H-pyrazol-5-amine

1-(1,3-dimethyl-1H-pyrazol-4-yl)-4,4,4-trifluoro-3-hydroxybut-2-en-1-one (Preparation 5, 1.7 g) and 3-bromo-1H-pyrazol-5-amine (Preparation 6, 1.18 g) in Acetic acid (52.61 mL) was heated at 120 C. in a sealed tube overnight. The reaction solution was cooled to room temperature, and poured into ice water (500 mL) resulting in a white precipitate. The precipitate was filtered and washed with copious amounts of water. The precipitate was then collected and dried in vacuo to afford the title compound as a white powder (1.9 g, 73.1%). [0524] 1HNMR (400 MHz, DMSO-d6) delta: 2.47 (s, 3H), 3.79, (s, 3H), 6.95, (s, 1H), 7.73, (s, 1H), 8.67, (s, 1H).

According to the analysis of related databases, 1203705-55-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boivin, Roch; Carlson, Eric; Endo, Atsushi; Hansen, Hans; Hawkins, Lynn D.; Ishizaka, Sally; Mackey, Matthew; Narayan, Sridhar; Satoh, Takashi; Schiller, Shawn; US2013/324547; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-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 1280210-79-8, Product Details of 1280210-79-8

Under N2 protection and a condition free of water and oxygen, Intermediate 2 (1000 mg, 4.78 mmol) was dissolved in N,N-dimethylformamide (15 ml), which was cooled to -15C, and sodium bis(trimethylsilyl)amide (4.78 mL, 2 mol/L, 9.56 mmol) was added, followed by stirring for 30 min, and S-cyclopentylsulfonyl chloride (1.37 g, 8.13 mmol) was added dropwise, followed by reaction for 16 hours at -15C. The temperature was raised to 0C, and the reaction was quenched by addition of water (20 ml) to the reaction solution, which was then extracted with ethyl acetate (20 ml*2). The organic phases were combined, dried over anhydrous sodium sulfate, concentrated, re-dissolved in tetrahydrofuran (20 ml), and cooled to a temperature between -10C and 0C, potassium t-butoxide (85 mg, 0.76 mmol) was added, and the reaction was allowed to proceed for 24 hours at this temperature. After the reaction was completed, a saturated aqueous solution of ammonium chloride (10 ml) and water (10 ml) were added. The solution was extracted with ethyl acetate (20 mL*3). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate (v/v) = 5:1) to obtain a white solid 6a (800 mg, yield 62%).

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; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 141573-95-7, A common heterocyclic compound, 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C8H10F2N2O2, 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.

Example 1Ethyl 5-chloro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate (III-1) 20.25 g (100 mmol) of ethyl 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate and 40 ml of SO2Cl2 are placed under argon and the mixture is heated to 60 C. and stirred at this temperature for 8 hours. After diluting the mixture with ethyl acetate, washing with water and removing the solvent under vacuum, 21 g of the product are obtained with an HPLC purity of 94%. M.p. 37-39 C.1H NMR (CDCl3): delta=7.1 (1H, t), 4.3 (q, 2H), 3.9 (s, 3H), 1.4 (t, 3H) ppm.19F NMR (CD3CN): delta=-114.9 (2F, t) ppm.

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; Bayer CropScience AG; US2011/288305; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 39806-90-1, name is 4-Iodo-1-methyl-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 39806-90-1, Recommanded Product: 4-Iodo-1-methyl-1H-pyrazole

To a mixture of Cul (6 mg, 0.033 mmol, 0.2 equiv.), 4-iodo-l -methyl- 1H- pyrazole (41 mg, 0.195 mmol, 1.2 equiv.) and K2CO3 (90 mg, 0.651 mmol, 4.0 equiv.) were added methyl 3-((4-chlorobenzyl)amino)-2-oxopyrrolidine-3-carboxylate (46 mg, 0.163 mmol, 1.0 equiv.) in anhydrous l,4-dioxane (2 mL) and N,N-dimethylethylenediamine (4 m^, 0.033 mmol, 0.2 equiv.). The resulting mixture was flushed with nitrogen, sealed, heated in an oil bath at 115 C for 18 h, cooled to room temperature, filtered through a syringe filter, and purified with reverse phase HPLC using 10% – 100% ACN / water (both with 0.1% formic acid; Phenomenex Gemini C18 5 micron column) to provide 8 mg (14%) of methyl 3- ((4-chlorobenzyl)amino)-l-(l-methyl-lH-pyrazol-4-yl)-2-oxopyrrolidine-3-carboxylate. LRMS (APCI) m/z 363.2 (M+H).

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; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 4149-06-8, These common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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 solution of 3-amino-1-phenyl-2-pyrazolin-5-one 1 (0.35 g, 2 mmol), dimedone 2 (0.28 g, 2 mmol), aldehyde 3 (0.28 mg, 2 mmol) and Cell-LA-TEA+/Fe3O4 nanocatalyst (0.03 g, 0.09 mol%) in H2O/EtOH (3:2) was subjected to ultrasonic irradiation (ultrasonic bath, room temperature). The progress of the reaction was controlled by TLC (hexane/ethyl acetate, 2:3). After reaction completion, the nanocatalyst was separated magnetically from the reaction mixture and used for subsequent cycles after washing with ethanol. By cooling the reaction solution, the solid product was collected, separated and recrystallized from methanol to get the pure product.

Statistics shows that 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one is playing an increasingly important role. we look forward to future research findings about 4149-06-8.

Reference:
Article; Zahedifar, Mahboobeh; Pouramiri, Behjat; Razavi, Razieh; Research on Chemical Intermediates; vol. 46; 5; (2020); p. 2749 – 2765;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 28466-26-4, name is 4-Aminopyrazole, 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 28466-26-4, Formula: C3H5N3

Step 2: To a solution of 5-(m-tolyl)oxazole-4-carboxylic acid (1 1.18 g) in DCM (65 mL), HOBT (1 1 .15 g, 0.083 mol) and EDC (15.8 g, 0.083 mol) was added at 0 C. This suspension was stirred at this temperature for 10 min, then it was added to a suspension was of 1 /-/-pyrazol-4-amine (5.48 g) and DIPEA (17.65 mL) in DCM (50 mL). The resulting mixture was allowed to warm to rt and was stirred at rt for 18 h. Percipitation of the desired compound was obtained by the addition of water. The solid was filtered and dried to yield the title compound. LC-MS conditions B: tR = 0.63 min, [M+H]+ = 269.13.

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; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2012/110986; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 34334-96-8, name is 3-Methyl-5-nitro-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 34334-96-8, Formula: C4H5N3O2

A solution of 5-methyl-3-nitro-lH-pyrazole (500 mg, 3.93 mmol) and potassium carbonate (1.08 g, 7.81 mmol) in acetonitrile (20 mL) was treated dropwise with 2- iodoethanol (2.00 g, 1 1.6 mmol) and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted with ethyl acetate (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, heptane to 1 : 1 ethyl acetate/heptane) to afford 2-(5-methyl-3-nitro-lH-pyrazol-l-yl)ethanol as a white solid: NMR (400 MHz, DMSO-i¾d 6.82 (s, 1H), 4.97 (t, J = 5.2 Hz, 1H), 4.19 (t, J = 5.2 Hz, 2H), 3.75 (q, J= 5.2 Hz, 2H), 2.35 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyl-5-nitro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter; CURRIE, Kevin, S; KROPF, Jeffrey, E.; LEE, Seung, H.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; XU, Jianjun; ZHAO, Zhongdong; WO2011/112995; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics