Month: September 2021

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. 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-carboxylate, A new synthetic method of this compound is introduced below., name: Ethyl 3-phenyl-1H-pyrazole-5-carboxylate

A mixture of ethyl 3-phenyl-lH-pyrazole-5-carboxylate (70.0′ g) , 2, 4-dichlorobenzyl chloride (69.6 g) , potassium carbonate (53.7 g) and N,N-dimethylformamide (400 ml) was stirred at room temperature for 15 hr, the reaction mixture was concentrated, and the residue was partitioned between water and ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSCU) / and concentrated. The residue was crystallized from ethyl acetate- hexane to give ethyl 1- (2, 4-dichlorobenzyl) -3-phenyl-lH- pyrazole-5-carboxylate (61.0 g, yield: 50%) as brown crystals, melting point 104-1070C.

The synthetic route of 13599-12-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/18314; (2007); A2;,
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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H6N2O

Step 2: 1 – methyl – l H-pyrazole-4-carbaldehyde oxime A mixture of the combined organic layer having 1 -methyl- l H-pyrazole-4-carbaldehyde and ethyl acetate obtained from step 1 , hydroxylamine hydrochloride (63.48 gm, 0.9135 moles) were refluxed at 70-80C for 2-4 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-5C, to this added DM water ( 100 ml) and 25% aqueous ammonia solution (100 ml) at 0-5C. The reaction mixture was stirred for 10 min at 20-30C. The organic layer was separated and aqueous layer was extracted with ethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (500 ml). Stirred for 10 min and separated the final aqueous layer and organic layer. The organic layer was evaporated to obtain the 1 -methyl- lH-pyrazole-4- carbaldehyde oxime. Dry wt : 60 gm Yield : 1.2 w/w (79%) HPLC purity : 99.78%

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 25016-11-9.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M.; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2111; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1453-58-3, name is 3-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 1453-58-3, SDS of cas: 1453-58-3

To a 10 ml Schlek reaction tube under the protection of an inert gas such as high purity nitrogen, 0.05 mmol of a water-soluble palladium on water-bound monophosphine salt compound (5), 1.0 mmol of p-chlorobenzene, 1.3mmol of 3-methylpyrazole, 3 mmol of potassium hydroxide and 5 ml of water were added and the reaction tube was purged with nitrogen three times and then heated to 100 C with an oil bath under magnetic stirring. The reaction was refluxed for 24 hours. The oil bath was removed and the reaction was concentrated on a rotary evaporator. The residue was chromatographed on silica gel using ethyl acetate as the developing solvent to give pure product 4-methylphenyl-3-methylpyrazole in 89%

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; Luoyang Normal College; Li Hongmei; Xu Chen; Tu Tianyong; Wang Zhiqiang; Hao Xinqi; (10 pag.)CN106674287; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 114474-28-1, The chemical industry reduces the impact on the environment during synthesis 114474-28-1, name is 4-(1H-Pyrazol-4-yl)aniline, I believe this compound will play a more active role in future production and life.

[0244] A mixture of 5,7-dichloro-l-methyl-lH-pyrazolo[4,3-d]pyrimidine (300 mg, 1.50 mmol), 4-(lH-pyrazol-4-yl)aniline (235, 1.50 mmol), and iPr2NEt (0.52 mL, 0.74 mmol) in DMF (3.0 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (465 mg, 97%). MS(ES+) m/e 326 (M+H)+.

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-(1H-Pyrazol-4-yl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; KIM, Ji-In; POYUROVSKY, Masha; LIU, Kevin; BARSOTTI, Anthony; MORRIS, Koi; (344 pag.)WO2016/210330; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1280210-79-8, 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. 1280210-79-8 name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, 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 tert-butyl 4,6-dihydropyrrolo[3,4- c]pyrazole-5(2H)-carboxylate (15.0 g, 71.8 mmol) in DMF (150 mL) was added NaH (60% in mineral oil) (8.6 g, 215.4 mmol) while the reaction mixture was cooled with an ice bath. When the addition was complete, the resulting mixture was allowed to warm to room temperature and was stirred at room temperature for 30 min. At this point, l-bromo-2- methoxyethane (19.8 g, 143.6 mmol) was added into the reaction mixture, and stirring was continued at room temperature for 2 h. The reaction mixture was then quenched with water (300 mL), and extracted with EtOAc (150 mL x 3). The combined organic layer was washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 30 : 1) to give a mixture of 122 and 122-A (19.0 g, 99%) as a colorless oil. MS 268.2 [M + H]+. [0072] Synthesis of 123 and 123-A. To a solution of 122 and 122-A (6.5 g, 24.3 mmol) in DCM (60 mL) cooled with an ice bath was added TFA (30 mL). The reaction mixture was stirred at room temperature for 1 h, whereupon the solvent was removed in vacuo to give 123 and 123-A as a crude product mixture which was used directly in the next step without further purification. MS 168.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; RODIN THERAPEUTICS, INC; FULLER, Nathan, Oliver; LOWE, John, A.; (45 pag.)WO2019/32528; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, molecular formula is C9H12N2O4, 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: C9H12N2O4

Example 27; Preparation of (5R, 6Z)-7-oxo-6- [ (4-oxo-6, 7-dihydro-4H-pyrazo . o [5, 1-c] [1, 4] oxazin-2- yl) methylene]-4-thia-1-azabicyclo [3. 2. 0] hept-2-ene-2-carboxylic Acid. Step 1: Diethyl 1- (2-frtert-butyl (dimethvl) silvlloxylethyl)-1H-ayrazole-3, 5- dicarboxvlate To a solution of diethyl 3, 5-pyrazoledicarboxylate (2.17 g, 10 mmol) in acetonitrile (10 ml), under nitrogen, was added potassium carbonate (2.07 g, 15 mmol), and 2- bromoethoxy-t-butyldimethylsilane (2.90 g, 12 mmol). The mixture was stirred at reflux for 18 hr. It was then cooled to room temperature, diluted with ethyl acetate (20 ml), and filtered through Magnesol. The filter pad was eluted wtih 2 x 10 mi of ethyl acetate, and the combined filtrate was evaporated. The residue was dissolved in hexanes and passed through a column of silica gel (70 g). After eluting with hexanes (100 ml), the column was eluted with ethyl acetate. The ethyl acetate eluent was evaporated to give 3.71 g of a colorless oil ; MS m/e 371 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 37687-24-4, its application will become more common.

Reference:
Patent; WYETH; WO2003/93277; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 694-48-4,Some common heterocyclic compound, 694-48-4, name is 1,3-Dimethyl-1H-pyrazole, molecular formula is C5H8N2, 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.

In a 5 L reactor, equipped with a stirrer, a reflux condenser, an argon inlet, thermometer and dropping funnel, 1,3-dimethyl-1H-pyrazole(500 g, 5.2 mol) was added slowly with stirring to acetic anhydride (1950 mL, 2125 g, 20.8 mol), while maintaining the temperature below 45 C. Concd H2SO4(50 mL, 92 g, 0.94 mol) was added with cooling and stirring and the mixture then was gradually heated to reflux and held at reflux for 6 h. The mixture was then cooled, evaporated at 70 C/7 Torr, and treated with crushed ice (2 kg). By carefully addition of 40% NaOH solution, the pH of the reaction mixture was adjusted to pH 8, then the organic phase was separated and the aqueous phase was extracted with CH2Cl2(2 × 1000 mL).The combined organic phases were washed successively with H2O(500 mL) and brine (500 mL), and dried over MgSO4. The solvent was removed at 7 Torr, and the residue was distilled (110-112 C/10 Torr) to afford the target ketone (452 g, 63%) as thick, light yellow oil, which crystallized upon standing.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dimethyl-1H-pyrazole, its application will become more common.

Reference:
Article; Taydakov, Ilya V.; Krasnoselskiy, Sergey S.; Synthesis; vol. 45; 15; (2013); p. 2188 – 2192;,
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 5932-27-4 as follows. Recommanded Product: Ethyl 1H-pyrazole-3-carboxylate

To a solution of ethyl 3-pyrazolecarboxylate (1.0 g) in N,N-dimethylformamide (7.0 mL) was added N-iodosuccinimide (1.6 g), and the mixture was stirred at room temperature for 1 hour, warmed to 60C, and then stirred for 0.5 hours. The reaction solution was returned to room temperature, saturated aqueous sodium bicarbonate and sodium sulfite were added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and then dried over sodium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain a compound 0215-1 (1.0 g) as a pale yellow solid.

According to the analysis of related databases, 5932-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; FURUYA, Kentarou; TERAO, Takahiro; SEKINE, Shinichirou; NAKAGAWA, Daisuke; EP2727920; (2014); A1;,
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. 612511-81-6, name is (1-Methyl-1H-pyrazol-3-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 612511-81-6

General procedure: N,N-Diisopropylethylamine (3.0?4.0 eq) was added to 8-methoxyquinoline-3-carboxylic acid (1.0 eq) in solvent (dichloromethane, tetrahydrofuran,or N,N-dimethylformamide, 0.05 to 0.2 M) at room temperature. Then, 1-((dimethylamino)(dimethyliminio)methyl)-1H-[1,2,3]triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate(V)(1.0?1.5 eq) was added and the reaction mixture was stirred for five minutes. Then, amine (1.0 ? 2.0 eq) was added and the reaction mixture was stirred for one to sixteen hours. 10percent Aqueous citric acid was added and the reaction mixture was extracted with dichloromethane, washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered,and concentrated. The resulting residue was purified by RP HPLC or silica gel chromatography to give the quinoline-3-carboxamide (1percent-95percent yield).

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 612511-81-6.

Reference:
Article; Deaton, David N.; Do, Young; Holt, Jason; Jeune, Michael R.; Kramer, H. Fritz; Larkin, Andrew L.; Orband-Miller, Lisa A.; Peckham, Gregory E.; Poole, Chuck; Price, Daniel J.; Schaller, Lee T.; Shen, Ying; Shewchuk, Lisa M.; Stewart, Eugene L.; Stuart, J. Darren; Thomson, Stephen A.; Ward, Paris; Wilson, Joseph W.; Xu, Tianshun; Guss, Jeffrey H.; Musetti, Caterina; Rendina, Alan R.; Affleck, Karen; Anders, David; Hancock, Ashley P.; Hobbs, Heather; Hodgson, Simon T.; Hutchinson, Jonathan; Leveridge, Melanie V.; Nicholls, Harry; Smith, Ian E.D.; Somers, Don O.; Sneddon, Helen F.; Uddin, Sorif; Cleasby, Anne; Mortenson, Paul N.; Richardson, Caroline; Saxty, Gordon; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1456 – 1478;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 181585-93-3,Some common heterocyclic compound, 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, molecular formula is C5H5N3O4, 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.

Step3: Methyl 5,7-dihydroxy-6-phenylpyrazolo[1 ,5-a]pyrimidine-2-carboxylate; A solution of 5.Og Methyl 3-amino-1 H-pyrazole-5-carboxylate, 8.3ml_ diethyl- phenylmalonate and 5OmL diisopropylethylamine in 5OmL DMF was heated to 1500C for 40h. The solvent was removed, the solid residue was dissolved in 2- propanol the mixture was stirred for 3 hours. The desired product was filtered, dried and was used without further purification. MS (M+1): 286 Characteristic 1 H NMR (300MHz, d6-DMSO) signals: 6.0 (s, 1 H); 3.8 (s, 3H)

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

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; VENNEMANN, Matthias; MAIER, Thomas; HOeLDER, Swen; BENEKE, Gerrit; DEHMEL, Florian; ZUeLCH, Armin; STRUB, Andreas; BECKERS, Thomas; INCE, Stuart; REHWINKEL, Hartmut; LIU, Ningshu; BOeMER, Ulf; WO2010/91808; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics