Tag: M.W=0-100

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. 1453-58-3, name is 3-Methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Methylpyrazole

250 mL of dimethyl sulfoxide and sodium hydride 24.0 g (60percent, petroleum ether washing) were added to a three-necked flask, and 41.0 g of 3-methylpyrazole was dissolved in 150 mL of dimethyl sulfoxide, and slowly added to the reaction flask. The reaction was carried out until no bubbles were evolved, and 101.5 g of p-methoxybenzyl bromide was added to maintain the temperature of the reaction system at 30 °C. After the reaction was completed, 1 L of ice water was added, and dichloromethane (200 mL × 3) was added, and the organic phase was combined, washed with water, washed with saturated sodium hydrogen carbonate, brine, and dried over anhydrous sodium sulfate.Concentration gave 99.6 g (98.5percent) of 1-(4′-methoxybenzyl)-3-methylpyrazole.

According to the analysis of related databases, 1453-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nantong University; Tang Yanfeng; Ding Xinyu; Shan Jiahui; Yu Hongmei; Wang Shuqing; Mao Jiarong; Guo Xiaoqing; (5 pag.)CN103880749; (2019); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 288-13-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 288-13-1 name is 1H-Pyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: Complex 2 (0.05 mmol) was added to a 5 mL of a sealed tube containing the aryl iodide or bromide (0.5 mmol), 1H-pyrazole (0.75 mmol), NaOH (1 mmol), and DMSO (1 mL). The mixture was stirred at 100 C for 12 h. After being cooled to room temperature, the mixture was quenched with 10 mL H2O and extracted with EtOAc(3 × 20 mL). The combined EtOAc extracts were dried with anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure.The residue was purified by flash column chromatography on silicagel with PE/EtOAc (from 10:1 to 5:1) as the eluent to afford the pure products. All N-aryl pyrazoles reported here are known products and were characterised by 1H NMR, and GC-MS.

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

Reference:
Article; Liu, Yan; Liu, Wei; Zhang, Qin; Liu, Ping; Xie, Jian-Wei; Dai, Bin; Journal of Chemical Research; vol. 37; 10; (2013); p. 636 – 637;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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. Recommanded Product: 3-Methylpyrazole

General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999percent purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98percent purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1453-58-3, its application will become more common.

Reference:
Article; Teo, Yong-Chua; Yong, Fui-Fong; Lim, Gina Shiyun; Tetrahedron Letters; vol. 52; 52; (2011); p. 7171 – 7174;,
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. 28466-26-4, name is 4-Aminopyrazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Aminopyrazole

1/-/-Pyrazol-4-amine (for a preparation see intermediate 1 ; 0.54 g, 6.5 mmol) was dissolved in acetonitrile (25 ml) with triethylamine (1.81 ml, 13.0 mmol) to give a red- purple suspension which was cooled in an ice-water bath. To the suspension was added a solution of 2,6-difluorobenzoyl chloride (Aldrich; 0.817 ml, 6.5 mmol) in acetonitrile (25 ml) dropwise over 15 min. The mixture was stirred cold under nitrogen. The reaction was stirred and allowed to warm slowly towards room temperature over 2 h, then at room temperature for 30 min. The reaction mixture was partitioned between EtOAc and water (-100 ml each). The aqueous phase was extracted with further EtOAc (2 x 50 ml). The combined organic extracts were dried (MgS04) and concentrated in vacuo. The residue (1.41 g) was purified on silica (50 g) using 0-100% EtOAc-cyclohexane then 0-20% methanol- EtOAc. Relevant fractions were concentrated in vacuo to give some pure product (0.925 g) and some less pure material (0.50 g). The latter material was re-purified on silica (20 g) using EtOAc to give further pure product (0.366 g). The two batches of pure product were combined to give the title compound (1.28 g) as a pale cream solid; LCMS (System 1): MH+= 224, tRET = 2.08 min.

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; GLAXO GROUP LIMITED; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; WO2012/52459; (2012); 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. 113402-89-4, name is 3-Methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H7N3

4-Bromo-6,7-dimethoxycinnoline (530 mg, 2.0 mmol), 5-methyl-4H-pyrazol-3-amine (150 mg, 1.5 mmol), toluene (4 mL), tris(dibenzylideneacetone)dipalladium(0) (45 mg, 0.049 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthane (70.0 mg, 0.121 mmol) and sodium tert-butoxide (1.80E2 mg, 1.87 mmol) were combined in a 10 mL sealed tube. The reaction was irradiated in a microwave on 300 watts, at 140°C for 600 seconds The reaction mixture was then filtered through Celite using methanol and methylene chloride and subsequently concentrated. The crude product was then dissolved in 1 mL methanol and filtered through a Gelman Acrodisk 0.45 micron HPLC filter. Purification using a C18 column preparative (30 x 00 mm) HPLC column and a gradient of 20-80percent acetonitrile:water (with 0.1percent formic acid) and a flow rate of 45 mL/min afforded 40.9mg (8percent) of 6,7-dimethoxy-N-(5-methyl-4H-pyrazol-3-yl)cinnolin-4-amine hydroformate as a yellow solid. MS [M+H] = 286.1, LC/MS (EI) tR 3.14 min (Method B), .H NMR (DMS0-d6) 8 (ppm) d 12.57 (s, 1 H), 9.38 (s, 1 H), 7.94 (s, 1 H), 6.12 (s, 1.5 H), 5.75 (s, 0.5 H), 4.01 (s, 3 H), 4.00 (s, 3 H), 2.30 (s, 3 H)

The synthetic route of 113402-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2006/28957; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1072-68-0, name is 1,4-Dimethylpyrazole, 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 1072-68-0, Recommanded Product: 1072-68-0

PREPARATION 129 (2-Bromo-5-fluorophenyl)(1 ,4-dimethyl-1 H-pyrazol-5-yl)methanol Sodium hydride (60% dispersion in mineral oil, 0.35 g, 8.65 mmol) was suspended in 12 ml tetrahydrofuran. A solution of 4-methyl-1 H-pyrazole (0.60 g, 7.3 mmol) in 2 ml tetrahydrofuran was added dropwise and the mixture was stirred for 1 h at room temperature. Methyl iodide (0.45 ml, 7.23 mmol) was added drop-wise and the mixture was stirred overnight forming a precipitate. The mixture was filtered and the solid was washed with a little tetrahydrofuran. The filtrates combined to give a crude solution of 1 ,4-dimethyl-1 H-pyrazole. The crude solution was cooled in an ice-bath and n-butyl lithium (1 .6 M in hexanes, 5.40 ml, 8.64 mmol) was added dropwise with stirring over 15 min under a nitrogen atmosphere. The cooling bath was removed and the mixture was stirred at ambient temperature for 2 h. The mixture was cooled to -78 C and a solution of 2-bromo-5- fluorobenzaldehyde (1 .76 g, 8.67 mmol) in 3 ml tetrahydrofuran was added over 1 min. The mixture was stirred overnight, warming to room temperature. The mixture was partitioned between saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue was purified using the Isolera purification system (ethyl acetate-hexane gradient, 0: 100 rising to 100:0) to give 720 mg (2.41 mmol, 33%) of the title compound as a white solid. Purity 100%. 1 H N MR (300 MHz, CHLOROFORM-d) delta ppm 7.45-7.54 (m, 2H), 7.19 (s, 1 H), 6.91 -6.98 (m, 1 H), 6.04 (s, 1 H), 3.84 (s, 3H), 2.70 (br s, 1 H), 1 .75 (s, 3H). UPLC/MS (3 min) retention time 1 .53 min. LRMS: m/z 299, 301 (M+1 ).

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; ALMIRALL, S.A.; VIDAL JUAN, Bernat; ALONSO DIEZ, Juan Antonio; BUIL ALBERO, Maria Antonia; EASTWOOD, Paul Robert; ESTEVE TRIAS, Cristina; LOZOYA TORIBIO, Maria Estrella; ROBERTS, Richard Spurring; VIDAL GISPERT, Laura; GONZALEZ RODRIGUEZ, Jacob; MIR CEPEDA, Marta; WO2013/10880; (2013); 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 31108-57-3 as follows. Formula: C4H3N3

EXAMPLE P7: Preparation of 1-[6-[3-chloro-6-(trifluoromethvnpyrazolo[4,3-clpyridin-2-yll-5- ethylsulfonyl-2-pyridyllpyrazole-4-carbonitrile (compound P10): (0692) (0693) To a solution of 3-chloro-2-(6-chloro-3-ethylsulfonyl-2-pyridyl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine (425 mg, 1 mmol) in N,N-dimethylformamide (4 mL) was added dipotassium carbonic acid (140 mg, 1 mmol), followed by 1 H-pyrazole-4-carbonitrile (93mg, 1 mmol). The mixture was stirred at room temperature for 3hrs. The reaction was diluted with ice water (20 ml), extracted with ethyl acetate (2×40 ml), the combined organic layers washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by combiflash (silica gel, 40% EA-cyclohexane) to afford 1-[6-[3-chloro-6-(trifluoromethyl)pyrazolo[4,3-c]pyridin-2-yl]- 5-ethylsulfonyl-2-pyridyl]pyrazole-4-carbonitrile (compound P10) as a solid, mp 251-253C. LCMS (method 3): 482/484 (M+H)+, retention time 1.50 min.

According to the analysis of related databases, 31108-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; SIKERVAR, Vikas; RAWAL, Girish; SEN, Indira; HALL, Roger, Graham; (117 pag.)WO2017/134066; (2017); 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. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Methyl-1H-pyrazol-3-amine

2-Bromo-5-fluoropyridine (1) (1 .Og, 5.71 mmcl), 1-methyl-I H-pyrazol-3-amine (2) (554mg, 5.7Immol), Xantphos (0.33g, 0.57mmol), and Cs2003 (2.79g, 8.56mmol) were combined in dry 1,4-dioxane (I5mL). The reaction mixture was degassed with N2(g) and placed under vacuum for 10mm. Pd2(dba)3 (0.26g,0.28mmol) was then added and the resulting reaction mixture was heated at90°C for 30h. It was then poured onto demineralized water (200mL), and extracted with EtOAc (3 x IOOmL). The organic phases were combined, dried over Na2SO4, filtered and subsequently evaporated under vacuum. The resulting residue was purified by flash chromatography, eluting with EtOAc/Hexane (1:1)to provide 5-fluoro-N-(1-methyl-IH-pyrazol-3-yl)pyridin-2-amine (3) as a yellow solid (0.65g, 61percent).LCMS (ES): Found 193.0 [MH]+.

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/72714; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 930-36-9, name is 1-Methylpyrazole, 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 930-36-9, Product Details of 930-36-9

Preparation 17-1) To a stirred mixture of bromine (50.2 ml) in dichloromethane (14) and anhydrous sodium carbonate (206.8 g) was added a solution of N-methylpyrazole (80 g) in dichloromethane (100 ml) at 0~5 C. After stirring for 1 hour at the same temperature, the mixture was stirred for a further one hour at room temperature and then ice cooled. To the reaction mixture, water (1 l) was added. The dichloromethane layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue was distilled in vacuo to afford 4-bromo-1-methylpyrazole (150.6 g). bp: 82 C. (20 mmHg) IR (Neat): 3100, 2930 cm-1 NMR (CDCl3, delta): 3.89 (3H, s), 7.38 (1H, s), 7.44 (1H, s) APCI-Mass (m/z): 161, 163 (MH+)

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, 1-Methylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5608056; (1997); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 31108-57-3, 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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of II-A13b To a solution of II-A12b (200 mg, 0.5 mmol) in acetone (3 mL) was added 4-cyanopyrazole (69.9 mg, 0.8 mmol) and K2C03 (345 mg, 2.5 mmol). The mixture was stirred at 25C for 16 hrs. To the mixture was added water (20 mL) and the mixture was extracted with EtOAc (2 x 20 mL). The organic layer was separated, concentrated and purified by flash column (0781) (25-60% EtOAc in PE) to give II-A13b (100 mg). The material (100 mg) was purified by HPLC separation to give II-A13b (4 mg, 2%) as a solid. (0782) 1H NMR (400 MHz, CDCf) dH 7.85-7.80 (m, 2H), 5.38-5.09 (m, 2H), 4.05 (t, J =1.6 Hz, 1H), 3.98 (s, 1H), 3.67 (dd, J= 8.0, 12.0 Hz, 1H), 1.95-1.66 (m, 7H), 1.52-1.37 (m, 8H), 1.35-1.19 (m, 7H), 1.17-1.00 (m, 1H), 0.86 (s, 3H); LC-ELSD/MS purity 99%, MS ESI calcd. for C^^NsOs [M +H]+ 412.2, found 412.2.

The chemical industry reduces the impact on the environment during synthesis 1H-Pyrazole-4-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (206 pag.)WO2019/140272; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics