Day: July 29, 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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

3-(difluoromethyl)-1-methyl-1H-pyrazol-4-carboxylic acid obtained by example 2 is treated with oxalyl chloride (1.25 eq) in toluene, and a few drops of dimethylformamide are added. The mixture is concentrated under reduced pressure to yield the carboxyl chloride.

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; SOLVAY FLUOR GmbH; Changzhou Keylab Biochemical Co., Ltd.; WANG, Mingchun; LI, Qingyi; (11 pag.)US2018/273486; (2018); 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 694-31-5 as follows. Quality Control of 1,5-Dimethyl-1H-pyrazole

N-Iodosuccinimide (35.8 g, 159 mmol) was added to a 10 C. solution of 1,5-dimethyl-1H-pyrazole (15.3 g, 159 mmol) in N,N-dimethylformamide (20 mL). The reaction mixture was stirred at 10 C. for 16 hours, and at 15 C. for 48 hours, whereupon it was diluted with ethyl acetate (500 mL) and washed sequentially with water (3*100 mL), aqueous sodium sulfite solution (100 mL), and saturated aqueous sodium chloride solution (50 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the product as a white solid. Yield: 28.0 g, 126 mmol, 79%. 1H NMR (400 MHz, CDCl3) delta 7.41 (s, 1H), 3.85 (s, 3H), 2.29 (s, 3H).

According to the analysis of related databases, 694-31-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; Kablaoui, Natasha Mariam; Green, Michael Eric; Montgomery, Justin Ian; Brodney, Michael Aaron; Verhoest, Patrick Robert; Kauffman, Gregory Wayne; Rankic, Danica Antonia; Mente, Scot Richard; Rogers, Bruce Nelsen; Arora, Kapildev Kashmirilal; Dunn, Matthew Francis; (98 pag.)US2018/148432; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5334-39-4, 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 5334-39-4 as follows.

To a stirred solution of 3-methyl-4-nitro-lH-pyrazole (1.24 g, 0.009 mol, 1 equiv) in DMF (20 mL) was added K2CO3 (1.86 g, 0.013 mol, 1 equiv) portion wise at 0C and stirred for 10 minutes. l-(bromomethyl)-2,4-bis(trifluoromethyl)benzene (3 gm, 0.009 mol, 1 equiv) was added drop wise 0C. The reaction mixture was allowed to stir for 1 hour at RT. Product formation was confirmed by LCMS. After completion of reaction, reaction mixture was diluted with water and extracted with ethyl acetate (100 mL x 3). Combined organic extracts were washed with water (100 mL x 4), dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain mixture of l-(2,4-bis(trifluoromethyl)benzyl)- 3-methyl-4-nitro-lH-pyrazole(peak 1) and l-(2,4-bis(trifluoromethyl)benzyl)-5-methyl-4- nitro-lH-pyrazole(peak 2). obtained crude was sent for separation in prep. LCMS: 353 [M+H] +.

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRAXIS BIOTECH LLC; ALFARO, Jennifer; BELMAR, Sebastian; NUNEZ VASQUEZ, Gonzalo Esteban; PUJALA, Brahmam; SATHE, Balaji Dashrath; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; THAKRAL, Pooja; PATIDAR, Rajesh Kumar; (344 pag.)WO2019/195810; (2019); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 313735-62-5, 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. 313735-62-5, name is 4-Bromo-1-isopropylpyrazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-bromo-l- (propan-2-yl)-lH-pyrazole (2 g, 10.58 mmol, 1.00 equiv) in Et20 (20 mL) maintained under nitrogen at -78 C was added dropwise a 2.5 M n-butyllithium solution (4.6 mL) in hexane. The reaction mixture was stirred at -78 C for 1 h. Sulfur dioxide gas was then bubbled in for 30 min. The reaction mixture was stirred at -78 C for 30 min and then warmed to rt. The solid was collected by filtration, washed with Et20 and dried in a vacuum to give 0.9 g (47%) of the title compound as a white solid. LCMS (Method G, ESI): RT =1.03 min, m/z = 191.0.

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

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; DRAGOVICH, Peter; ZAK, Mark; ZHAO, Guiling; ZHENG, Xiaozhang; WO2014/74715; (2014); 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. 5334-43-0, name is 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., name: 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

General procedure for diazotization of aminopyrazoles 1a-d and aminoimidazoles 2a-c: Aqueous NaNO2 (1.8 mmol, 1 mL) was added to a well-stirred and cooled solution (0-5 C) of pyrazole or imidazole (1 mmol) in a mixture of HCl/AcOH (3:1, 20 mL) over a period of 10 min. The reaction mixture was allowed to warm at room temperature and was stirred for 20 h. The precipitate of pyrazolotriazinone or imidazotriazinone was then filtered off, and the residue was diluted with water (20 mL), extracted with dichloromethane (3 × 30 mL), and dried with anhydrous MgSO4. The resulting solution was concentrated to dryness, and the solid was then subject to chromatographic column separation with dichloromethane and dichloromethane/ethyl acetate in different proportions.

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:
Article; Colomer, Juan Pablo; Moyano, Elizabeth Laura; Tetrahedron Letters; vol. 52; 14; (2011); p. 1561 – 1565;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, 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 1-Methyl-1H-pyrazol-3-amine

Step 1: (S) -tert-Butyl (1- (2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) -4- ( (1-methyl-1H-pyrazol-3-yl) carbamoyl) oxazol-5-yl) ethyl) carbamate[2043]To 15 mL of dichloromethane were added (S) -5- (1- ( (tert-butoxycarbonyl) amino) ethyl) -2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) oxazole-4-carboxylic acid (250 mg, 0.53 mmol) , 3-amino-1-methylpyrazole (62 mg, 0.64 mmol) , 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (153 mg, 0.80 mmol) and 1-hydroxy-7-azabenzotriazole (182 mg, 1.33 mmol) . To the mixture was added N, N-diisopropylethylamine (0.37 mL, 2.14 mmol) dropwise at 0 . The resulting mixture was stirred at rt for 3.5 hours. The reaction mixture was washed with water (10 mL × 2) and the organic layer was dried over anhydrous sodium sulfate. The organic solvent was removed and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 2/1) to give a white solid (260 mg, 85) .[2044]1H NMR (400 MHz, CDCl3) : delta ppm 7.59 (s, 1H) , 7.58 ?7.55 (m, 1H) , 7.31 (d, J 2.1 Hz, 1H) , 7.25 (d, J 8.8 Hz, 1H) , 6.79 (d, J 2.2 Hz, 1H) , 6.71 (t, JF-H 75.1 Hz, 1H) , 5.36 ?5.32 (m, 1H) , 4.00 (d, J 7.0 Hz, 2H) , 3.86 (s, 3H) , 1.56 (d, J 7.0 Hz, 3H) , 1.43 (s, 9H) , 1.37 ?1.32 (m, 1H) , 0.73 ?0.68 (m, 2H) , 0.46 ?0.42 (m, 2H) and MS-ESI: m/z 548.8 [M+H]+.

The synthetic route of 1-Methyl-1H-pyrazol-3-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; YU, Tianzhu; ZHANG, Yingjun; ZHANG, Xiangyu; ZHANG, Shiguo; CHENG, Changchung; ZHANG, Jiancun; WO2015/161830; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H12N2O4

reparation of intermediate 11-7; To a solution of diethyl 3,5-pyrazoledicarboxylate (1 g, 4.712 mmol) in acetone (20 ml), 2-bromo-3′-methoxyacetophenone (1.079 g, 4.712 mmol) and potassium carbonate (0.716 mg, 5.184 mmol) were added. The reaction mixture was stirred at RT 12h. The solvent was evaporated and residue was dissolved in DCM and washed with water. The organic phase was dried over Na2S04 and concentrated in vacuo. The residue, a yellow oil, (1.605g, 95% yield) was used in the next reaction step without further purification as intermediate II-7.

The synthetic route of 37687-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; RAMOS LIMA, Francisco, Javier; WO2011/89400; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

1572-10-7, name is 3-Amino-5-phenylpyrazole, 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. category: pyrazoles-derivatives

General procedure: The general method was described for the synthesis of D1. Compound C1 (150 mg, 0.393 mmol) was dissolved in ethanol (2 mL),followed by addition of 5-phenyl-1H-pyrazol-3-amine (62.63 mg, 0.393 mmol) and triethylamine (119.43 mg, 1.18 mmol). The mixture was stirred at room temperature for 5 h. The resultant mixture was purified by column chromatography to give D1.

The synthetic route of 1572-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin; Chinese Chemical Letters; vol. 31; 2; (2020); p. 418 – 422;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 179692-08-1, 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. 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 15, Step C [00154] To a solution of compound 15c (38 g, 143 mmol) in acetonitrile (380 mL) at r.t. was added K2C03 (39.5 g, 286 mmol) and then PMBCI (24 mL, 177 mmol). The reaction mixture was stirred at 60C overnight. After cooling to r.t., the mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford compound 15d (32 g, 58%).[00155] This compound was characterized by proton NMR (1HNMR) and mass spectroscopy (MS) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): delta 8.13(s, 1 H), 7.23(d, J = 8.8 Hz, 2H), 6.90(d, J = 8.8 Hz, 2H), 5.29(s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H); 1.26(t, J = 6.8 Hz, 3H). Mass spectroscopy indicated MS (ESI): m/z 387 (M+H)+.

The synthetic route of Ethyl 4-iodo-1H-pyrazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

1904-31-0, name is 1-Methyl-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. COA of Formula: C4H7N3

Synthesis Example 4 Synthesis of ethyl 3-chloro-1-methyl-5-pyrazolecarboxylate (Compound No. 4.3 (a) of the invention) 6.5 g of 3-amino-1-methylpyrazole was dissolved in 55 ml of conc. hydrochloric acid. To this solution was added dropwise a solution of 6.22 g of sodium nitrite in 12.5 ml of water while maintaining the temperature of from 0° to 5° C. through cooling with ice. After the completion of the dropwise addition, the stirring was continued at this temperature for 1 hour. The above-mentioned diazonium solution was added dropwise to a suspension of 7 g of cuprous chloride in 55 ml of chloroform. 2 g of cuprous chloride were twice added thereto during that time. After the completion of the dropwise addition, the mixture was reacted at 50° C. for 5 hours, and was then stirred at room temperature for 15 hours. This solution was filtered using a Celite, and was then neutralized with a sodium carbonate aqueous solution. The chloroform layer was extracted, and the aqueous layer was further extracted twice with 50 ml of chloroform. The combined chloroform solution was washed with a saturated aqueous solution of sodium chloride, and was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 7 g of a crude product. This crude product was purified through silica-gel column chromatography to obtain 5.2 g of 3-chloro-1-methylpyrazole as a yellow oil.

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

Reference:
Patent; Nissan Chemical Industries, Ltd.; US5817829; (1998); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics