Tag: M.W:100-200

Some common heterocyclic compound, 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H6F2N2O2, 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: C6H6F2N2O2

To a 200 ml single-neck round bottom flask was added 28.39 mmol 3 dissolved in 40 ml of dichloromethane, and then 31.32 mmol of triethylamine was added. Stir for 10 minutes; Further adding 31.23 mmol of EDCI and catalytic amount of DMAP to the reaction. Stir at room temperature for 30 minutes. Finally, 28.39 mmol of N,O-dimethylhydroxylamine hydrochloride was added to the system. Stir at room temperature overnight, after the reaction is completed, The mixture was suction filtered under reduced pressure and the filtrate was concentrated to remove solvent. It was dissolved in 20 ml of dichloromethane and diluted. Wash once with 30 ml of water, separate the aqueous layer and extract twice with dichloromethane (10 ml × 2). The combined organic layers were washed once with 20 ml of saturated sodium chloride solution. The aqueous layer was separated and extracted twice with dichloromethane (10 mL×2). The combined organic layers were dried over anhydrous sodium sulfate; The filtrate is concentrated to remove the solvent.With petroleum ether / ethyl acetate (2:1, volume / volume) purification by column chromatography to give a white solid 6; yield 91%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 176969-34-9, its application will become more common.

Reference:
Patent; Nankai University; Fan Zhijin; Yu Bin; Yang Dongyan; Zhao Bin; Guo Xiaofeng; Zhang Nailou; Hao Zesheng; Wu Qifan; Zhou Shuang; Cao Lixin; (36 pag.)CN110128419; (2019); A;,
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 113100-53-1 as follows. Recommanded Product: 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

General procedure: To a solution of carboxylic acid (1 equiv) in CH2Cl2 or DMF (1 mL) was added HOBt (1.2 equiv) and DIEA (2 equiv). After the mixture was stirred at room temperature for 5 min, EDCI (1.1 equiv) and corresponding amine (1.3 equiv) were added. The mixture was stirred overnight, diluted with ethyl acetate (40 mL), washed with 1 N HCl (10 mL), saturated NaHCO3 (20 mL), H2O (20 mL), brine (20 mL), dried over Na2SO4, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel.

According to the analysis of related databases, 113100-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cheng, Gang; Muench, Stephen P.; Zhou, Ying; Afanador, Gustavo A.; Mui, Ernest J.; Fomovska, Alina; Lai, Bo Shiun; Prigge, Sean T.; Woods, Stuart; Roberts, Craig W.; Hickman, Mark R.; Lee, Patty J.; Leed, Susan E.; Auschwitz, Jennifer M.; Rice, David W.; McLeod, Rima; Bioorganic and Medicinal Chemistry Letters; vol. 23; 7; (2013); p. 2035 – 2043;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6994-25-8, name is Ethyl 3-amino-1H-pyrazole-4-carboxylate, 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 6994-25-8, SDS of cas: 6994-25-8

Example 29[00239] Example 29 presents the preparation of Cmpd 29, N-(5-fluoropyrimidin-2-yl)- 4,5,6,7-tetrahydropyrazolo[3′,4′:6,7]cyclohepta[1,2-d][1 ,3]thiazol-2-amine (Table II, Compound No. 29)[00240] To a solution of t-BuONO (124 g, 1.20 mol) in 3 L MeCN was added CuBr2 (279 g, 1.20 mol). The mixture was stirred at room temperature for 1 h under nitrogen, then compound 29a (160g, 1.03 mol) was added in portions over 30 min. The mixture was stirred at room temperature under nitrogen for 30 min, then heated to 70C and stirred for an additional 2h. After cooling to r.t., the solvent was removed in vacuo. The residue was diluted with EtOAc (3 L) and washed with brine (400 mL.x3). The organic layer was dried over MgS04, filtered, and concentrated to afford the crude product 29b (200 g, 89% yield) used directly in the next step without purification.

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Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA S.A.; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; YUNFU, Luo; WO2012/8999; (2012); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5203-77-0, These common heterocyclic compound, 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, 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.

Weigh 4.0g (0.036mol) 1,3- dimethyl-5-pyrazolone-ol in 250mLthree-necked flask was added 50mL1,2-Dichloroethane was dissolved, weighing 12g (0.12mol) oftriethylamine in the system. Under ice cooling, the mixture of intermediate(b-2)The reaction solution (0.030mol press note) was addeddropwise to the system, a solution process using argon. After the reaction 1hHPLC trace transShall, after completion of the reaction raw reaction solutioncontaining the intermediate (b-3) a. To the reaction solution containingintermediate (b-3) in additional3.0g (0.030mol) of triethylamine and 0.5mL acetonecyanohydrin, temperature control and the use of argon, the reaction 2h at 50 ~60 ,The reaction was followed by HPLC. After completion of thereaction was added 100mL of water was slowly added dropwise HCl, stirring atroom temperature, until pH = 3 or so. ExtractionThe aqueous layer was removed, and the organic layer waswashed twice with 200mL of water, dried over anhydrous sodium sulfate, theorganic solvent was removed by rotary evaporation to afford 8.1gA tan solid, a powdered compound b.

The synthetic route of 5203-77-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lian, Lei; Zheng, Yurong; He, Bin; Pengxue, Gang; Jin, Tao; Cui, Qi; (63 pag.)CN105503728; (2016); A;,
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. 154471-65-5, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H5F3N2

To a mixture of 8.71 g of l-methyl-3-trifIuoromethyl-1H-‘ pyrazole and 130 ml of tetrahydrofuran was added dropwise 32 ml of a 2.0 mol/L lithium diisopropylamide solution in heptane/tetrahydrofuran/ethylbenzene at -78C. The mixture of stirred at -780C for 2 hours and then poured into a mixture was dry ice and 50 ml of tetrahydrofuran. The mixture was stirred for 2 hours while allowing it to rise to around room temperature. Water and diethyl ether were poured into the reaction mixture. The aqueous layer was adjusted to pH 10-12 by an addition of a 2N aqueous sodium hydroxide solution, and then layers were separated. The resulting aqueous layer was washed with diethyl ether two times, adjusted to around pH 3 by an addition of 2N hydrochloric acid, and then extracted with methyl tert-butyl ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure to obtain 8.19 g of l-methyl-3- tri f luoromethyl- lH-pyra zole- 5-carboxylic acid of the formula :l-Methyl-3-trifluoromethyl-lH-pyrazole-S-carboxylic acid EPO 1H-NMR (CDCl3, TMS) delta (ppm) : 4.13 (3H, s) , 7.22 (IH, s).

The synthetic route of 154471-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2007/43677; (2007); 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. 3920-40-9, name is 4-Amino-1-methyl-1H-pyrazole-3-carboxamide, A new synthetic method of this compound is introduced below., COA of Formula: C5H8N4O

Stage c A mixture of 2-(3-methanesulphonylphenyl)thiazole-4-carboxylic acid (120 mg) from stage b and 4-amino-1-methyl-1H-pyrazole-3-carboxamide (65 mg) in triethylamine (176 muL) and DMF (3 ml) in the presence of HATU (209 mg) is stirred at room temperature for 88 h. Water is added, the mixture is extracted with ethyl acetate and the organic phase is concentrated. Purification by preparative HPLC and purification by column chromatography on silica gel (mobile phase cyclohexane/acetone) result in 2-(3-methanesulphonylphenyl)thiazole-4-(3-carbamoyl-1-methyl-1H-pyrazol-4-yl)carboxamide (3.4 mg) as a white solid. C16H15N5O4S2, M=405.1; LC-MS (ZQ): Rt=0.92, m/z=406 [M+H]+. 1H-NMR (300 MHz, D6-DMSO): 3.31 (s, 3H), 3.90 (s, 3H), 7.56 (s, 1H), 7.72 (s, 1H), 7.84 (m, 1H), 8.07 (m, 1H), 8.32-8.38 (m, 2H), 8.43 (m, 1H), 8.55 (s, 1H), 11.3 (s, 1H)

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; Ulrich, BOTHE; Arne, Von Bonin; Duy, Nguyen; Ulf, Bomer; Judith, Guenther; US2009/163486; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

852227-86-2, name is 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole, 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: C6H9ClN2

A mixture of N-(1 -methylcyclopropyl)-3-[(1 -metriylpyrazol-4-yl)metriyl]-2-oxo- 7H-quinoline-6-sulfonamide (60 mg, 0.16 mmol), 5-(chloromethyl)-1 ,3-dimethyl- 1H -pyrazole (23 mg, 0.16 mmol), potassium carbonate (45 mg, 0.32 mmol) and potassium iodide (27 mg, 0.16 mmol) in DMF (2 mL) was heated with agitation in the microwave at deltaOmicron ‘ for 30 minutes. The solvent was removed in vacuo and the residue purified by prep HPLC (high pH) affording the desired product (20 mg, 0.042 mmol, 26%) as a white powder.

The synthetic route of 852227-86-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); 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 26621-44-3 as follows. name: 3-Nitro-1H-pyrazole

3-Nitropyrazole (11.3 g, 0.1 mol) at room temperature,Benzyl bromide (17.1 g, 0.1 mol), tetrabutylammonium bromide (1.6 g, 0.005 mol), dissolved in 10 ml of dimethyl sulfoxide (DMSO).Add sodium hydroxide solution [sodium hydroxide solution: 8.8 g (0.22 mol)The solution obtained by dissolving sodium hydroxide in 10 ml of water], the reaction is exothermic,After the dropwise addition is completed, the mixture is stirred at room temperature overnight, and diluted with water to quench.Extract with dichloromethane, dry, concentrate and recrystallize with semi-dry petroleum ether.The product was obtained in 18.3 g with a yield of 90%.

According to the analysis of related databases, 26621-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (16 pag.)CN108863936; (2018); A;,
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 3112-31-0 as follows. Product Details of 3112-31-0

To a 25 mL reactor, 174.0 mg of 3,5-pyrazoledicarboxylic acid monohydrate and 250.0 mg of copper sulfate pentahydrate powder were added, 5 mL of pyridine and 10 mL of water were added, and after stirring for 15 minutes, the reaction kettle was placed in an oven and heated to 180. °C, reaction for 24 hours; After the reaction is completed, the reaction solution is transferred to a flask, and 2 mL of a saturated aqueous solution of sodium sulfide is added to the reaction solution, and after the precipitation is completed, it is filtered:Add 1M hydrochloric acid solution to the filtrate droplet obtained in the second step, adjust the solution pH=3, and filter;The filtrate obtained in the third step was extracted with an organic solvent dichloromethane (3×20 mL), and the organic phase was collected and dried over anhydrous sodium sulfate for 10 h;The organic phase obtained after the fourth step of drying was concentrated and dried to obtain 100 mg of a white powder, which was designated as sample 1.

According to the analysis of related databases, 3112-31-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Fujian Structure Of Matter Institute; Huang Deguang; Xiang Shiqun; Zhang Xiaofeng; (13 pag.)CN109369617; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 15366-34-4,Some common heterocyclic compound, 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, molecular formula is C5H6N2O2, 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.

1 -Chloro-4-iodo-benzene (3.5 g, 14.7 mmol), methyl 1 H-pyrazole-3-carboxylate (1.85 g, 14.7 mmol) and Cul (0.235 g, 1.47 mmol), L-proline (0.405 g, 2.94 mmol), K2C03 (4.1 g, 29.4 mmol) in DMSO (40ml_) were stirred at 90 C for10 hours. The reaction mixture was filtered and the organic layer was diluted with EtOAc (300 ml_), washed with brine (100 ml. x 3), and dried over Na2S04. Evaporation of the solution on a water bath under reduced pressure gave methyl 1 -(4-chlorophenyl)pyrazole-3-carboxylate (2.3 g, 66% yield).

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

Reference:
Patent; BASF SE; WINTER, Christian; RHEINHEIMER, Joachim; WOLF, Antje; TERTERYAN, Violeta; POONOTH, Manojkumar; WIEBE, Christine; KREMZOW-GRAW, Doris; ROeHL, Franz; ROHRER, Sebastian Georgios; WIEJA, Andy; ROSENBAUM, Claudia; GRAMMENOS, Wassilios; WO2014/202703; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics