Day: June 22, 2021

Application of 139308-52-4, The chemical industry reduces the impact on the environment during synthesis 139308-52-4, name is Ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

(4-(((Trans)-4-morpholinocyclohexyl)amino)quinazolin-6-yl)boronic acid (30 mg, 0.084mmol) was dissolved in EtOH (1 mL) and added to a vial containing ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate (29.0 mg, 0.126 mmol) and Si-DPP-Pd (64.8 mg, 0.0 17mmol). Potassium carbonate (1M in water, 0.084 ml, 0.168 mmol) was added, the vial wassealed and the resulting mixture was then heated to 125 C for 10 minutes under microwave irradiation. The mixture was filtered and purified by mass triggered reverse phase HPLC (ACN/water with 0.1% TFA modifier) to afford the title product as a TFA salt. MS: 465 (M+1). ?H NMR (DMSO-d6, 600 MHz) oe 9.79 (s, 1H), 8.89 (s, 1H), 8.75 (s, 1H), 8.48 (s,1H), 8.25 (d, J = 8.69 Hz, 1H), 7.81 (d, J = 8.67 Hz, 1H), 4.39 (br s, 1H), 4.14 (q, J = 7.10 Hz, 2H), 4.02-4.00 (m, 2H), 3.95 (s, 3H), 3.71-3.69 (m, 2H), 3.44-3.39 (br s, 1H), 2.52-2.50 (m, 4H), 2.20-2.18 (m, 2H), 2.10-2.08 (m, 2H), 1.64-1.58 (m, 4H), 1.16 (t,J= 7.10 Hz, 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, Ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; ANDRESEN, Brian, M.; BRUBAKER, Jason, D.; CHILDERS, Matthew, L.; DONOFRIO, Anthony; FISCHMANN, Thierry; GIBEAU, Craig, R.; KATTAR, Solomon, D.; LESBURG, Charles, A.; LIM, Jongwon; MACLEAN, John, K. F.; MANSOOR, Umar, F.; NORTHRUP, Alan, B.; SANDERS, John, M.; SMITH, Graham, F.; TORRES, Luis; (91 pag.)WO2016/53771; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35344-95-7,Some common heterocyclic compound, 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 1Hpyrazole4carbaldehyde (1.00 g, 10.40 mmol) and 6bromo4methylnicotinonitrile (2.05 g, 10.40 mmol) in dioxane (15 mL) were added K2CO3 (4.31 g, 31.20 mmol). The resulting reaction mixture was degassed with nitrogen for 5 minutes then copper (I) iodide (0.59 g, 3.12 mmol) was added, followed by transN,N’dimethylcyclohexane1,2diamine (2.59 mL, 16.4 mmol). The resulting mixture was degassed again for 10 minutes and heated at 110 °C for 1 h under microwave irradiation. The reaction mixture was cooled to ambient temperature, filtered through Celite® and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2040percent EtOAc/ nhexane) to obtain Intermediate 6 (1.15 g, 52.10percent) as pale yellow solid. 1H NMR (300 MHz, DMSOd6) G^ppm 2.62 (s, 3 H), 8.10 (s, 1 H), 8.38 (s, 1 H), 8.95 (s, 1 H), 9.37 (s, 1 H), 9.98 (s, 1 H). LCMS (methodD), retention time 1.68 min, [M+H] 213.2.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol, 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 132712-71-1, Formula: C4H6N2O

General procedure: To a neat solution containing 11H-indeno[1,2-b]quinoxalin-11-one (1 mmol), pyrazolone (1 mmol), and malononitrile (1 mmol), 10% mol of Na2CO3 in ethanol(10 mL) was added. The reaction mixture was heated at 70 8C for 12 h. After completion of the reaction as indicated by TLC, the precipitate was filtrated and washed with cold ethanol to afford the pure product 8. 4.6 6′-amino-3′, 7-dimethyl-1’H-spiro [indeno[1,2-b]quinoxaline-11′,4-pyrano[2,3-c] pyrazole] carbonitrile (8b) Light brown powder (0.35 g, yield 90%). Mp 258-262 C. IR (KBr) 3445, 3250, 3224, 2966, 3110, 2193, 1638, 1597, 1447, 1398. 1H NMR (250 MHz, DMSO-d6): deltaH (ppm) 1.13 (3H, s, CH3), 2.58 (3H, s, CH3-Ar), 7.32-8.14 (9H, m, H-Ar and NH2), 12.6 (1H, s, NH). 13C NMR (62 MHz, DMSO-d6): deltaC (ppm) 8.9 (CH3), 21.1 (CH3-Ar), 56.5 (C-Spiro), 96.3 (C-CN), 118.7 (CN), 121.4, 125.6, 127.8, 128.6, 129.4, 131.5, 132.7, 135.6, 139.7, 140.4, 142.0, 150.8, 152.6, 155.0, 162.4 (C-Ar and C-Pyrazole), 163.3 (C-NH2). Anal. calcd for C23H16N6O: C, 70.40; H, 4.11; N, 21.42. Found: C, 70.44; H, 4.14; N, 21.39.

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, 3-Methyl-1H-pyrazol-5-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Soleimani, Ebrahim; Hariri, Mina; Saei, Parisa; Comptes Rendus Chimie; vol. 16; 9; (2013); p. 773 – 777;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, 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 28466-26-4 as follows.

3-(2-(Methoxycarbonyl)phenyl)acrylic acid (1.23 g, 5.97 mmol) was weighed.EDCI (1g, 5.24mmol), DMAP (0.35 g, 2.87 mmol) was dissolved in THF (18 mL) and stirred at room temperature.Compound 1H-pyrazole-4-amine (0.56 g, 5.6 mmol) was then added.The system was stirred at room temperature overnight.Add water to filter the sediment,Concentration in vacuo gave a crude product (yield: 0.72 g, 2.66 mmol) as a white solid.

According to the analysis of related databases, 28466-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing University of Technology; Zhang Na; Qi Xiaoqian; Li Chunqiong; Zhao Lijiao; Zhong Rugang; (8 pag.)CN109879808; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 17827-60-0,Some common heterocyclic compound, 17827-60-0, name is Methyl 1-Methylpyrazole-5-carboxylate, molecular formula is C6H8N2O2, 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 methyl l-methyl-lH-pyrazole-5-carboxylate (3 g, 21.4 mmol) in tetrahydrofuran (50 mL) at 0 C was added lithium aluminum hydride (977 mg, 25.7 mmol). The mixture was stirred at room temperature for 12 h. The reaction was quenched by adding water, extracted with ethyl acetate (100 mL), dried, concentrated and the residue was purified by column chromatography on silica gel (petroleum ether/ acetic ester =10: 1), to afford the title compound as an off-white oil (2 g, 83.3%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-Methylpyrazole-5-carboxylate, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COOK, Andrew; COTE, Alexandre; DAKIN, Les, A.; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NASVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2014/151142; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 174891-10-2, name is 5-Amino-1H-pyrazole-3-acetic acid, 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 174891-10-2, SDS of cas: 174891-10-2

mixture of 4-chloro-5-(2-chloroethoxy)-7-(2-methoxyethoxy)quinazoline (2.01g, 6.34mmol), (3-amino-lH-pyrazol-5-yl)acetic acid (0.89g, 6.31mmol) and hydrogen chloride (1.6ml of a 4M solution in 1,4-dioxane, 6.4mmol) in dimethylacetamide (20ml) were stirred at room temperature for 4 hours. The resulting thick suspension was added to water (100ml) then 40% aqueous sodium hydroxide solution added to pEta 12. 2N Hydrochloric acid was then added to re-adjust the pH to 4.8. The resulting pale orange solid was filtered, washed with water and dried over phosphorus pentoxide under high vacuum to give (3-{[5-(2- chloroethoxy)-7-(2-methoxyethoxy)quinazolin-4-yl]amino}-lH-pyrazol-5-yl)acetic acid (2.45g, 92% yield). MS (+ESI): 422 (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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/67391; (2006); 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. 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 5-nitro-1H-pyrazole-3-carboxylate

To a solution ofmethyl3-nitro-1H-pyrazole-5-carboxylate (342 mg, 2.0 mmol) macetone (40 mL) was added 1,2-dibromoethane (412 mg, 2.2 mmol), followed by K2C03 (828mg, 6. 0 mmol). The resulting mixture was stirred to reflux for 2 hrs. Then K2C03 was filteredoff The filtrate was concentrated in vacuo to give a residue, which was purified by silica gelcolumn (DC.lV1/MeOH = 50/1) to afford methyll-(2-bromoethyl)-3-nitro-lH-pyrazole-5-carboxylate (430 mg, yield: 77%) as yellow solid.[001034] 1H NMR (400 rviHz, CDCb): J = 7.42 (s, 1H), 5.08 (t, J = 6.4 Hz, 2H), 3.97 (s, 3H),3.78 (t, J = 6.4 Hz, 2H).

The synthetic route of 181585-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JECURE THERAPEUTICS, INC.; STAFFORD, Jeffrey A.; VEAL, James M.; TRZOSS, Lynnie Lin; MCBRIDE, Christopher; (411 pag.)WO2018/136890; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, 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. name: 3-(Trifluoromethyl)-1H-pyrazole

Step A: Preparation of N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide To a solution of 3-trifluoromethylpyrazole (5.0 g, 36 mmol), triethylamine (7.0 mL, 50 mmol) in dichloromethane (40 mL) was added dimethylsulfamoyl chloride (5.5 mL, 51 mmol), and the reaction mixture was heated at reflux for 2 days. The resulting mixture was cooled to ambient temperature and filtered through a pad of silica gel using dichloromethane as eluent. The filtrate was then concentrated under reduced pressure to give an amber residue. The resulting residue was dissolved in diethyl ether. The ether solution was washed with water, dried (MgSO4), and concentrated under reduced pressure to give 8.71 g of the title compound. 1H NMR (CDCl3): delta 3.01 (s, 6H), 6.65 (s, 1H), 8.03 (s, 1H).

The synthetic route of 20154-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gregory, Vann; Pasteris, Robert James; US2010/240619; (2010); 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. 1120-82-7, name is (1H-Pyrazol-1-yl)methanol, A new synthetic method of this compound is introduced below., Recommanded Product: 1120-82-7

General procedure: Step 2: The reaction was performed under argon by using standard Schlenk techniques. To a cold (0?C) solution of 1-(2-hydroxymethyl)-3,5-dimethylpyrazole (1.0?g, 8?mmol) in chloroform was added dropwise thionyl chloride (1.15?mL in 15?mL of CHCl3) and the mixture was refluxed for 4?h. The precipitate (1-(2-chloromethyl)-3,5-dimethylpyrazole, 79% yield) was collected, washed with diethyl ether and dried.

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:
Article; Coelho, Felipe Lange; Dresch, Lucielle Codeim; Stieler, Rafael; Campo, Leandra Franciscato; Schneider, Paulo Henrique; Catalysis Communications; vol. 121; (2019); p. 19 – 26;,
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. 118430-73-2, name is 3-(tert-Butyl)-1-methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 118430-73-2

Pyrazole 5 (673 mg, 4.4 mMol), diisopropylethylamine (684 mg, 5.3 mMol, 1.2 eq.), and DCM (9 mL) were cooled to -10 C. and phenyl chloroformate (750 mg, 4.8 mMol, 1.1 eq.) was added in a single portion. The solution was allowed to warm to 0 C. and stir for 30 min. The solution was partitioned between ether and aqueous sodium bicarbonate and the ether layer was washed with brine. The organic fraction was dried over anhydrous sodium sulfate and the solvent removed in vacuo and the residue purified using silica gel chromatography eluting with ethyl acetate (5%-50%)/hexane. Solvent removal afforded the product (6) as brittle foam (1.0 g, 3.9 mMol, 90% yield), which provided a single peak by LC-MS analysis (M+H=274.1). 1H NMR (400 MHz, CDCl3) delta: 7.4 (dd, J=8.0, 7.6 Hz, 2H), 7.25 (tt, J=7.6 Hz, 1H), 7.18 (d, J=8.0 Hz, 2H), 6.95 (brs, 1H), 6.15 (s, 1H), 3.79 (s, 3H), 1.29 (s, 9H).

The synthetic route of 118430-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Holtzman, Michael; Romero, Arthur; Alevy, Yael; Patel, Anand; Brett, Thomas; Patel, Dhara; US2015/183777; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics