Category: pyrazoles-derivatives

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

Application of 143426-52-2, 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. 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (182 mg, 0.60 mmol, 1.0 eq.), cesium carbonate (585 mg, 1.80 mmol, 3.0 eq.), 1-(4-(chloromethyl)phenyl)-1H-pyrazole (173 mg, 0.90 mmol, 1.5 eq.) and Pd(dppf)Cl2.DCM (66 mg, 0.090 mmol, 0.15 eq.) were combined in a vial which was sealed and placed under an inert atmosphere. A 1,4-dioxane/H2O solution (5:1 v/v, 4 mL, degassed) was then added via syringe. The resulting mixture was heated to 90 C. for 1.5 h, after which time the reaction was cooled to r.t. and filtered through a plug of Celite with EtOAc and DCM. Solvents were concentrated under reduced pressure, and crude residue was purified by column chromatography (3-100% EtOAc in hexanes, then 0-5% MeOH in DCM) to give the title compound as a brown solid (22 mg, 11% over 3 steps). ES-MS [M+H]+=334.3.

The synthetic route of 1-(4-(Chloromethyl)phenyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Conn, P. Jeffrey; Engers, Darren W.; Engers, Julie L.; Long, Madeline; Bender, Aaron M.; US2020/131180; (2020); 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 27006-76-4 as follows. Product Details of 27006-76-4

General procedure: To a solution of acetonitrile (20 mL), compound 3 (0.02 mol), benzyltriethylamine chloride (0.001 mol), KOH (0.024 mol), and appropriate phenols were added and refluxed for 5-48 h. The solvent was removed to give a residue under reduced pressure, which was dissolved with CH2Cl2 and washed using 10% KOH solution. Anhydrous MgSO4 was used to dry the dichloromethane layer. Compounds 4a-4l and 5a-5l were obtained after evaporation of the solvents, which were used to prepare compounds 6a-6l and 7a-7l without purification.

According to the analysis of related databases, 27006-76-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Song, Ming-Xia; Wu, Yi; Deng, Xian-Qing; Letters in drug design and discovery; vol. 13; 8; (2016); p. 800 – 808;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1260243-04-6,Some common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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.

General procedure: A mixture of ethyl-5-amino-1H-pyrazole-4-carboxylate 1 (1.0 mmol), an appropriate aldehyde 2 (1.0 mmol) and aterminal alkyne 3 (1.0 mmol) in acetic acid (5 mL) was stirred at 25 °C for 10 min. The mixture was then stirred at 60 °C under ultrasound using a laboratory ultrasonic bath SONOREX SUPER RK 510H model producing irradiationof 35 kHz for 30 min in the presence of air. The increase of bath temperature beyond 60 °C due to the prolonged ultrasound irradiation was controlled by adding cold water time to time. After completion of the reaction the mixture was cooled to room temperature, poured into ethyl acetate (25 mL) and washed with brine solution (2 x 15 mL) followed by 10percent NaHCO3 solution (2 x 15 mL). The organiclayer was collected, dried over anhydrous Na2SO4, filteredand concentrated under low vacuum. The residue isolatedwas purified by column chromatography over silica gel using3-8percent petroleum ether-EtOAc to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 5-amino-1H-pyrazole-4-carboxylate, its application will become more common.

Reference:
Article; Suresha, Namburi; Durgaraoa, Bodapati Veera; Ratnakar; Kolli, Sunder Kumar; Ashfaq, Mohd Ashraf; Rao, Mandava V. Basaveswara; Pal, Manojit; Letters in drug design and discovery; vol. 14; 10; (2017); p. 1176 – 1183;,
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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 37622-90-5

To a solution of 12 4,4,5,5-tetramethyl-2-(2-(3-(trifluoromethyl)benzyl)-1-benzothiophen-7-yl)-1,3,2-dioxaborolane (4) (1.25g, 3.0mmol) and 46 ethyl 1H-pyrazole-4-carboxylate (840mg, 6.0mmol) in 47 pyridine (10mL) was added 48 Cupric acetate, monohydrate (1.19g, 6.0mmol) at room temperature. The mixture was stirred at 50C under a dry atmosphere (CaCl2 tube) overnight. The mixture was quenched with 49 water at room temperature and extracted with EtOAc. The organic layer was separated, washed with 1M HCl and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0-25% EtOAc in 50 hexane) to give 51 5 (557mg, 43%) as colorless crystals. 1H NMR (300MHz, CDCl3) delta: 1.39 (3H, t, J=7.1Hz), 4.29 (2H, s), 4.36 (2H, q, J=7.1Hz), 7.08-7.11 (1H, m), 7.38-7.57 (6H, m), 7.68 (1H, dd, J=6.6, 2.2Hz), 8.18 (1H, s), 8.50 (1H, s).

According to the analysis of related databases, 37622-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nakahata, Takashi; Tokumaru, Kazuyuki; Ito, Yoshiteru; Ishii, Naoki; Setoh, Masaki; Shimizu, Yuji; Harasawa, Toshiya; Aoyama, Kazunobu; Hamada, Teruki; Kori, Masakuni; Aso, Kazuyoshi; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1598 – 1608;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 277299-70-4,Some common heterocyclic compound, 277299-70-4, name is 2-(3,4-Dimethylphenyl)-5-methyl-1H-pyrazol-3(2H)-one, molecular formula is C12H14N2O, 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.

b 4-{[1-(3,4-Dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl]azo}-3-hydroxybenzoic Acid Following the procedure of Example 1, except substituting 1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one for 3-methyl-1-(4-methylphenyl)-3-pyrazolin-5-one, the title compound was prepared as an orange solid (1.5 g, 82%). 1H NMR (400 MHz, d6-DMSO) delta 13.5 br s, 1H), 11.0 (s, 1H), 7.70 (m, 2H), 7.61 (dd, J=8.2 and 2.1 Hz, 1H), 7.53 (m, 2), 8.20 (d, J=8.2 Hz, 1H), 2.30 (s, 3H), 2.27 (s, 3H), 2.22 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3,4-Dimethylphenyl)-5-methyl-1H-pyrazol-3(2H)-one, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US6642265; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

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-Amino-1-phenyl-1H-pyrazol-5(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
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

Electric Literature of 17635-45-9, 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. 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred suspension of thioacid (1.0 mmol) in THF (5 mL) were added I2 (0.6 mmol, 152 mg), DIPEA (1.2 mmol, 0.156 mL) and HOBt (2.0 mmol, 270 mg) at r.t., followed by the appropriate amine(1.1 mmol). The reaction mixture was stirred for 0.5 to 1 h as analyzed by TLC (until complete disappearance of the thioacid was observed). After the reaction was complete, the solvent was evaporated under vacuum and diluted with EtOAc (20 mL). The organic phase was washed with 10percent HCl (2 × 10 mL), 1 N Na2CO3(3 × 10 mL), H2O (2 × 10 mL) and brine (10 mL) and then dried over anhydrous Na2SO4. The solvent was filtered and evaporated under reduced pressure. The crude reaction mixture was purified under column chromatography using hexane?EtOAc (7:3) as the eluentto afford the desired product.

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, 4-Pyrazol-1-yl-phenylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Madhu, Chilakapati; Vishwanatha; Sureshbabu, Vommina V.; Synthesis; vol. 45; 19; (2013); p. 2727 – 2736;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics