Tag: M.W:100-200

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. 876343-24-7, name is 1-Ethyl-1H-pyrazol-4-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Ethyl-1H-pyrazol-4-amine

EXAMPLE 187: 4-[4-(l-EthyMNo.-pyrazol-4-ylamino)-7No.-pyrroIo[2,3-“npyrimidin-6-yI]-3,6-dihydro-2No.-pyridine-l-carboxylic acid fcrf-butyl ester.; [527] A mixture of 4-(4-chloro-7No.-pyrrolo[2,3 -d]pyrimidin-6-yl)-3 ,6-dihydro-2No.-pyridine-1-carboxylic acid fert-butyl ester (HOmg, 0.33mmol) and l-ernyl-4-amino-l./:/’-pyrazole (44mg, 0.39mmol) in 1-butanol (3mL) was heated at 120°C overnight, LC-MSshowed the desired product and some de-Boc product. After the mixture was cooled to rt, itwas diluted with methylene chloride (3mL), then AyV-diisopropylethylamine (0.1 ImL,0.66mmol) and di-tert-butyldicarbonate (72mg, 0.33mmol) were added, the resulting mixturewas stirred at rt for 30min. The mixture was diluted with EtOAc (30mL), then washed withbrine (20mL), and dried over anhydrous sodium sulfate. The solvent was evaporated underreduced pressure, and the residue was crystallized with EtOAc to give, the title compound asan off-white solid. LC-MS (ES, Pos.): 410 [MH*]. ‘HNMR (CDC13, 400 MHz): 8 = 1.51 (s,9H), 1.56 (t, J = 7.3 Hz, 3H), 2.50 (m, 2H), 3.66 (m, 2H), 4.16 (m, 2H), 4.22 (q, J = 7.3 Hz,2H), 6.04 (s, 1H), 6.17 (s, 1H), 6.57 (s, 1H), 7.56 (s, 1H), 7.95 (s, 1H), 8.38 (s, 1H), 10.96 (brs, 1H).

The synthetic route of 876343-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3398-16-1, 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. 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a dry three-necked flask with a magnetic rotor was added 4-bromo-3,5-dimethylpyrazole (3.5714 g, 20 mmol, 98%, 1.0 eq.), phenylboronic acid (2.9552 g, 24 mmol, 99%, 1.2 equivalents),Palladium acetate (0.1123 g, 0.5 mmol, 0.025 equivalent), ligand S-Phos (0.5027 g, 1.2 mmol, 98%, 0.06 equivalent), 1,4-dioxane (60 mL) and potassium carbonate (8.2920 g, 60 mmol, 3.0 eq.) of aqueous solution (20 mL).Nitrogen was bubbled for 15 minutes and then the reaction flask was placed in a 115 C oil bath.After stirring for 15 hours, the reaction was monitored by thin layer chromatography. It was cooled to room temperature and extracted with dichloromethane (20 mL×3).All organic phases were combined and dried over anhydrous sodium sulfate.Filtration, concentration, and purification of the crude product by flash chromatography on silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 3/1 – 1/2) to give 3,5-dimethyl-4-phenyl -1H-imidazole,The white solid was 3.0773 g, and the yield was 89%.

The synthetic route of 4-Bromo-3,5-dimethylpyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; Dai Jianxin; She Yuanbin; Chen Shaohai; (127 pag.)CN108659050; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

Step j04: 3-Tert-butyl-1 H-pyrazol-5-amine (J-lll) (1 eq., 40 g) was dissolved in dilute HCI (120 ml of HCI in 120 ml of water) and mixed dropwise with NaNO2 (1.03 eq., 25 g in 100 ml) at 0 – 5 C over a period of 30 min. After stirring for 30 minutes, the reaction mixture was neutralised with Na2C03. A diazonium salt obtained by reaction of KCN (2.4 eq., 48 g), water (120 ml) and CuCN (1.12 eq., 31 g) was added dropwise to the reaction mixture within 30 min and the mixture was stirred for a further 30 min at 75 C. After complete reaction, the reaction mixture was extracted with EE (3 x 500 ml), the combined organic phases were dried over sodium sulphate and the solvent was removed under vacuum. The purification (Si02, 20 % EE/hexane) of the residue by column chromatography produced a white solid (J- IV) (6.5 g, 15.1 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-5-tert-butylpyrazole, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; FRORMANN, Sven; WO2012/62463; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 31037-02-2, 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. 31037-02-2 name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-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.

EXAMPLE IX.5 This Example illustrates a preparation of ethyl 5-(4,4-difluorobut-3-enylthio)-1-methylpyrazol-4-yl carboxylate (Compound IX.34). Bis-(4,4-difluorobut-3-enyl)disulfide (2.90 g) and tert.butyl nitrite (1.22 g) in acetonitrile (40 cm3) were heated to 60 C. under an atmosphere of nitrogen. To the stirred solution was added dropwise ethyl 5-amino-1-methylpyrazol-4-yl carboxylate (1.00 g) in acetonitrile (10 cm3). On complete addition the reaction solution was heated for 2 hours at 60 C., evaporated under reduced pressure and fractionated by chromatography (silica; hexane:diethyl ether, 5:1 by volume) to give Compound IX.34 (yield 42%). M+ =276; 1 H NMR: delta 1.38(3H,t); 2.20(2H,m); 3.05(2H,t); 3.97(3H,s); 4.25(1H,m); 4.34(2H,q); 7.98(1H,s); (oil).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Zeneca Limited; US5705516; (1998); A;,
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

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

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

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

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

Application of 16617-46-2, 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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Following the procedure described in Example 1 wherein 2-methoxyethanol was used as the solvent instead of ethanol, 76percent of the product was obtained with m. p. 184-187 °C.

The synthetic route of 3-Amino-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENTIVA, A.S.; WO2004/37824; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics