Category: pyrazoles-derivatives

These common heterocyclic compound, 49633-25-2, name is 3-Isopropylpyrazole, 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. Computed Properties of C6H10N2

Following the procedure of Example 36, Part B, but substituting 3-isopropylpyrazole for 4-bromo-3-isopropylpyrazole, there was prepared 3-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide having a boiling point at 83 C. at 0.03 mm Hg. About 10% of the 5-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide isomer was present.

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

Reference:
Patent; The Upjohn Company; US3957480; (1976); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

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.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

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

These common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, 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. Quality Control of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

Under argon, the goodsN-Boc-protected pyrazolopyrrolidine (1) (1 eq.) Was mixed in dry acetonitrile and sodium hydride (1.2 eq.) Was added slowly with ice bath cooling. The reaction mixture was stirred for 2 hours at room temperature.The resulting white suspension, iceUnder cooling in the bath, the product trideuteromethanesulfonyl chloride (methanesulfonyl chloride-D3) (2) (2 equivalents) is added slowly.After the addition was completed, the mixture was further stirred at 25 C for 1 hour.LC-MS and TLC showed that the basic reaction of the intermediate was completed.The reaction was quenched by addition of water and extracted with methylene chloride. The organic phases were combined and washed with water.Dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography to give tert-butyl 1- (trideuteromethylsulfonyl) -4,6-dihydropyrrolo [3,4-c] pyrazole- 5 (1H) Ester.

The synthetic route of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Ji Bell Pharmaceutical Co., Ltd.; Zhenjiang Sheng’an Pharmaceutical Co., Ltd.; Geng Zhongyi; Chen Xinghai; (20 pag.)CN107337674; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic 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 176969-34-9, COA of Formula: C6H6F2N2O2

To a one-necked flask was added 53.00 g 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid and 72 mL of thionyl chloride,Heating up to the system has a reflow phenomenon,After refluxing for 2 h, the unreacted thionyl chloride was evaporated at atmospheric pressure.System cooling to 60 below, an external anhydrous calcium chloride drying tower,Water pump vacuum distillation of low boiling impurities, get red viscous liquid, placed overnight solidified into white crystals.The yield was 78.25%.

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; Zhejiang Chemical Institute Co., Ltd.; Sinochem Lantian Group Co., Ltd.; Zhu Bingchun; Peng Weili; Yuan Jing; Huang Hongying; Yu Jiping; Wei Youchang; Kong Xiaolin; Chen Jie; (36 pag.)CN106810545; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 175137-46-9, 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. 175137-46-9 name is 5-Cyclopropyl-1H-pyrazol-3-amine, 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.

To a solution of 1,2,3-trifluoro-4-nitrobenzene (3.2 g, 18 mmol) and DIEA (4.2 ml, 24 mmol) in dry THF (20 ml) was added dropwise the solution of 5-cyclopropyl-lH-pyrazol-3- amine (2.0 g, 16 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 21 hrs. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 5. : 2). Recrystallization from EtOAc (10 ml) and hexanes ((at)100 ml) gave the title compound as red crystals (1.5 g, 33%). NMR (400 MHz) 11.90 (s, 1H), 8.78 (s, 1H), 7.86 (t, J= 7.6 Hz, 1H), 7.08 (q, J= 8.7 Hz, 1H), 5.60 (s, 1H), 1.83 (m, 1H), 0.89 (m, 2 H), 0.65 (m, 2H). MS: Calcd. : 280; Found: [M+H]+ 281.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, 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 31108-57-3, SDS of cas: 31108-57-3

General procedure: The appropriate carboxylic acid (1.0 equiv) was treated with oxalylchloride (1.1 equiv) in CH2Cl2 (0.5 M) at 0 C. The reaction mixture wasstirred at room temperature for 1 h. The solvent was removed under N2and the acid chloride (1 equiv) was dissolved in anhydrous CH2Cl2(0.5 M). The appropriate pyrazole (1.0 equiv) was dissolved in CH2Cl2(0.5 M) and cooled to 0 C. The acid chloride (1 equiv) in CH2Cl2 (0.5 M) was added dropwise and the reaction mixture was stirred atroom temperature for 3 h. The mixture was diluted with EtOAc, washedwith saturated aqueous NaCl, and dried over Na2SO4. Evaporationunder reduced pressure yielded the crude product that was purified byflash chromatography (SiO2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Pyrazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Otrubova, Katerina; Chatterjee, Shreyosree; Ghimire, Srijana; Cravatt, Benjamin F.; Boger, Dale L.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1693 – 1703;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 578008-32-9, These common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, 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.

The product of the previous step (6.6 g, 14.8 mmol), tert-butyl 3-amino-S-methyl- 1H-pyrazole-1-carboxylate (3.5 g, 17.7 mmol), cesium carbonate (9.61 g, 29.6 mmol) andPd Xphos (2.32 g, 2.95 mmol) were dissolved in dioxane (130 mL) and purged with nitrogen. The reaction mixture was stirred at 110 C for 12 h. The product was combined with the product of a similar reaction, extracted with EtOAc (600 mL) and washed with brine (3 x 300 mL). The organic layer was evaporated. The residue was crystallized to provide the title intermediate (5 g, 58 % yield) and 2 g of cmde product which waspurified by preparative HPLC (method 2).

Statistics shows that tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 578008-32-9.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; HUDSON, Ryan; KOZAK, Jennifer; FATHEREE, Paul R.; PODESTO, Dante D.; BRANDT, Gary E.L.; FLEURY, Melissa; BEAUSOLEIL, Anne-Marie; HUANG, Xiaojun; THALLADI, Venkat R.; (121 pag.)WO2016/191524; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 158001-28-6,Some common heterocyclic compound, 158001-28-6, name is 5-Amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile, molecular formula is C8H12N4, 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 mixture of 5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile (8, 1.1 g, 6.7 mmol) in formamide (15 ml) under a nitrogen atmosphere was heated in a microwave at 180 C for 30 min. The mixture was extracted with EtOAc (3 x 30 ml) and the organic layer was washed successively with sodium carbonate (30 ml), water (30 ml) and brine (30 ml). The organic layer was dried with magnesium sulfate, filtered and concentrated via evaporation of the solvent under a reduced pressure. The product was isolated as a brown solid in 77 % yield (0.97 g, 5.1 mmol). 1H NMR (200 MHz, CDCl3) delta 8.31 (s, 1 H), 7.85 (s, 1 H), 6.17 (s, 2 H), 1.77 (s, 9 H); 13C NMR (50 MHz, CDCl3) delta 157.9, 154.4, 153.2, 128.9, 102.1, 60.4, 29.2; HRMS (CI) calcd for C9H13N5 (M) 191.1171, found 191.1180.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile, its application will become more common.

Reference:
Article; Todorovic, Nick; Awuah, Emelia; Shakya, Tushar; Wright, Gerard D.; Capretta, Alfredo; Tetrahedron Letters; vol. 52; 44; (2011); p. 5761 – 5763;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 25016-17-5, name is Methyl 5-methyl-1H-pyrazole-3-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. Formula: C6H8N2O2

General procedure: A mixture of 1 (5.68 mmol) and potassium tert-butoxide (7.59 mmol) in 80 ml of anhydrous THF was heated under reflux for 1 h. After cooling to 0 C, a solution of ethylbromoacetate (7.78 mmol) in 20 ml of THF was slowly added. The reaction mixture was then stirred for 5 h at room temperature. The resulting mixture was filtered and the solvent was evaporated to dryness. The obtained residue was purified on alumina using dichloromethane as eluant.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25016-17-5, its application will become more common.

Reference:
Article; Radi, Smaail; Yahyi, Abderrahmane; Ettouhami, Abdelkader; Chaudhary Jha, Ambika; Adarsh; Robeyns, Koen; Garcia, Yann; Polyhedron; vol. 85; (2015); p. 383 – 388;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

16461-94-2, name is 4-Bromo-1H-pyrazol-3-amine, 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. Recommanded Product: 4-Bromo-1H-pyrazol-3-amine

A. A solution of 3-amino-4-bromopyrazole (2.0 g, 12 mmol) and 1 ,1 ,3,3- tetramethoxypropane (4.1 mL, 25 mmol) in acetic acid (5 mL) was heated at reflux for 4 h. Water (2 mL) was added and the mixture heated at reflux for a further 0.5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was triturated in methanol. The solid thus obtained was washed with cold methanol, ethyl acetate, and hexanes to provide 3-bromopyrazolo[1 ,5-a]pyrimidine as a brownish solid in 39% yield (0.953 g): 1H NMR (300 MHz, DMSO-d6) £9.13 (d, J = 6.5 Hz, 1 H), 8.61 (s, 1 H), 8.35 (s, 1 H), 7.19-7.02 (m, 1 H); MS (ES+) m/z 197.9 (M + 1), 199.9 (M + 1).

The synthetic route of 16461-94-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; LIU, Shifeng; FOCKEN, Thilo; CHAHAL, Navjot; ZHANG, Zaihui; OBALLA, Renata, Marcella; FONAREV, Julia; WO2013/64984; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics