Tag: M.W:100-200

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, category: pyrazoles-derivatives

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

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

Synthetic Route of 15878-00-9,Some common heterocyclic compound, 15878-00-9, name is 4-Chloro-1H-pyrazole, molecular formula is C3H3ClN2, 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 83 trans-4-Chloro-2′-cyclopropyl-2’H-[1,3′]bipyrazolyl-4′-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide Sodium hydride (60% in oil; 57 mg, 1.43 mmol) was added to a solution of 4-chloro-pyrazole (148 mg, 1.43 mmol) in dry DMF (25 mL) under nitrogen at 0 C. in an ice-water bath and the mixture was heated to 40 C. for 1 h. trans-5-Chloro-1-cyclopropyl-1H-pyrazole-4-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (60 mg, 0.18 mmol) was added and the mixture was heated at 110 C. overnight and then cooled. After the DMF was evaporated in vacuo, water and dichloromethane were added. The organic layer was separated, and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were concentrated in vacuo and the residue was purified by C-18 reverse phase preparative-HPLC with a gradient of 10-90% acetonitrile/water to give trans-4-chloro-2′-cyclopropyl-2’H-[1,3′]bipyrazolyl-4′-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (56 mg, 77%). LRMS m/z calcd for C20H24ClN5O2 (M+H) 402.2, found 402.2.

The synthetic route of 15878-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, Kevin William; Fotouhi, Nader; Gillespie, Paul; Goodnow, Robert Alan; Guertin, Kevin Richard; Haynes, Nancy-Ellen; Myers, Michael Paul; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Rossman, Pamela Loreen; Scott, Nathan Robert; Thakkar, Kshitij Chhabilbhai; Tilley, Jefferson Wright; Zhang, Qiang; US2007/225280; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 58607-90-2,Some common heterocyclic compound, 58607-90-2, name is Ethyl 5-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O3, 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.

[00230] To a solution of ethyl 5-oxo-4,5-dihydro-1 H-pyrazole-3-carboxylate (9.5 g , 60.8 mmol) in DCM and DMF (Volume: 1 25.5 ml, Ratio: 7:1 ) was added imidazole (6.21 g, 91 mmol) and TBDMSCI (1 0.09 g, 66.9 mmol) at 0 C. The reaction mixture was warmed up to room temperature and stirred for overnight. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered off, and dried in vacuo. The crude product was used for the next step without further purification. LCMS (m/z) : 271 [M+H]+. 1 H NMR (500 MHz, CDCI3) : (0402) 6.16 (s, 1 H), 4.37 (d, J=7.09 Hz, 2H), 1 .38 (t, J=7.09 Hz, 3H) , 0.98 (s, 9H), 0.27 (s, 6H).

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-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Jiping; HAN, Wooseok; JIN, Xianming; PFISTER, Keith Bruce; YOUNG, Joseph Michael; (68 pag.)WO2019/123285; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 60061-60-1, The chemical industry reduces the impact on the environment during synthesis 60061-60-1, name is 4-Bromo-3-isopropyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Part B – 4-Bromo-3-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide Sodium hydride (2.4 g., 0.06 mole) (57% oily dispersion) was washed with dry toluene (50 ml.) and then suspended in dry toluene (50 ml.). 4-Bromo-3-isopropylpyrazole (5.7 g., 0.03 mole) in toluene (10 ml.) was added drop by drop to the sodium hydride suspension, the mixture heated to reflux, and then treated dropwise with a solution of 2-chloro-N,N-dimethylpropionamide (8.1 g., 0.06 mole). Heating was continued for 4 hours, the mixture cooled, and treated with toluene (60 ml.) and water (40 ml.). The toluene layer was washed with water, (2 * 60 ml.), dried (magnesium sulfate) and the solvent removed under reduced pressure. The resulting oil was distilled to yield 4-bromo-3-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide (5.7 g., 67%) with a boiling point of 99 to 101 C. at 0.03 mm Hg. On standing, the oil solidified to give crystals having a melting point at 63 to 65 C.

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-Bromo-3-isopropyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

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

Synthetic Route 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

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. 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-(Furan-2-yl)-1H-pyrazol-3-amine

General procedure: A mixture of aldehyde (1.5 mmol), amine (3 mmol) and p-toluenesulphonic acid monohydrate (0.011 g, 0.06 mmol) in ethanol (10 mL) was heated to reflux for 2 h. After cooling, the precipitate was filtered off, washed with a little cold ethanol and dried in vacuo over anhydrous CaCl2.

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 96799-02-9.

Reference:
Article; Markovic, Violeta; Eric, Slavica; Stanojkovic, Tatjana; Gligorijevic, Nevenka; Aranelovic, Sandra; Todorovic, Nina; Trifunovic, Snezana; Manojlovic, Nedeljko; Jelic, Ratomir; Joksovic, Milan D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 15; (2011); p. 4416 – 4421;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 25016-11-9, 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 25016-11-9 as follows.

Potassium terf-butoxide (23.47 g of 95%, 199.1 mmol, 2.44 equiv.) was suspended in anhydrous DME (90 mL) and cooled to – 60 0C. TosMIC (23.76 g, 121.7 mmol, 1.49 equiv.) was dissolved in anhydrous DME (75 mL), and this was added drop-wise to the potassium terf-butoxide solution over 20 minutes. After stirring for 20 minutes between – 60 and – 55 0C, the compound of formula IX, in anhydrous DME (55 ml_), was added over 23 minutes. The reaction was stirred one hour at – 55 to – 50 0C to yield a thick suspension. Methanol (90 ml_) was then added resulting in a clear brown solution. The cooling bath was removed, and after stirring 5 minutes in air, the reaction flask was immersed in an oil bath preheated to 85 0C. The reaction was stirred for 1 hour. After cooling, the mixture was concentrated and the resulting tan solid was dissolved in water (180 ml_) with acetic acid (9 ml_). This was extracted with ethyl acetate (3 x 250 ml_), and these extracts were combined, washed with saturated aqueous sodium chloride (100 ml_), dried over sodium sulfate, filtered and concentrated to yield a brown oil (13.71 g). This oil was dissolved in dichloromethane and purified by silica-gel chromatography using a gradient from 0% to 15% dichloromethane-acetone to yield the compound of formula Xl as a bright yellow oil (7.89 g, 63% yield).

According to the analysis of related databases, 25016-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; WO2008/153870; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 64517-88-0, A common heterocyclic compound, 64517-88-0, name is 1,3-Dimethyl-1H-pyrazol-4-amine, molecular formula is C5H9N3, 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.

[6]; 2-(6-Chlorobenzotriazol-l-yl)-l,l,353-tetramethyluronium tetrafluoroborate was used in place of 2-(7-azabenzotriazol-l-yl)-l,l,353-tetramethyluronium hexafluorophosphate(V) as the coupling agent. The product gave the following characterising data :- 1H NMR Spectrum: (DMSOd6) 2.12 (s, 3H), 3.66 (s, 2H), 3.7 (s, 3H), 3.78 (s, 3H)5 4.02 (s, 3H)5 6.51 (d, IH), 6.88 (m, IH)5 7.03 (d, IH), 7.22 (s, IH)5 7.35 (d, IH)5 7.81 (s, IH), 8.77 (d, IH)5 9.43 (s, 2H); Mass Spectrum: M+H+ 434.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application 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