Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, 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 39806-90-1, Formula: C4H5IN2

Step 1: Prepartion of tert-but 4-(l-methyI-lH-pyrazoI-4-yl)-3-oxopiperazine~l- carboxylate: tot-Butyl 3-oxopiperazine-l-carbox late (0.164 g, 0.819 mmol) was suspended in isopropanol (3 mL) under an atmosphere of nitrogen and treated with l-methyl-4-iodo-lH- pyrazole (0.204 g, 0.983 mmol, 1.20 equiv), ethylene glycol (0.051 g, 0.82 mmol, 1.0 equiv). copper iodide (0.03 g, 0.16 mmol, 0.20 equiv), and potassium phosphate (0.695 g, 3.28 mmol, 4.00 equiv), and placed into a preheated oil bath at 100 C for 8 hours. The mixture was cooled to ambient temperature, concentrated in vacuo and the residue was dissolved in dichloromethane, washed with water, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 0: 100 hexanes : ethyl acetate), providing the titled compound.

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; MERCK SHARP & DOHME CORP.; BESHORE, Douglas, C.; KUDUK, Scott, D.; WO2011/137049; (2011); 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. 56984-32-8, name is Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 56984-32-8

Example 11; [Show Image] Compound 6 was reacted with various benzylalcohols to give Compounds A-21, A-22, A-23 and A-24 via Mitsunobu reaction.

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; Shionogi & Co., Ltd.; EP1953145; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, molecular formula is C4H3N3O4, 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. SDS of cas: 5334-40-7

A mixture of 4-nitro-3-pyrazolecarboxylic acid (4.98 g, 31.7 mmol), trans 4-aminocyclohexanol (3.65 g, 31.7 mmol), EDAC (6.68 g, 34.8 mmol) and HOBt (4.7 g, 34.8 mmol) in DMF (120 ml) was stirred at ambient temperature for 16 hours. The mixture was reduced in vacuo, the residue taken up in CH2CI2 and washed successively with 5percent citric acid, saturated aqueous sodium bicarbonate, water and brine. The product was found to be mainly in the citric acid wash, which was basified and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and evaporated to give a white solid, which was triturated with CHCI3 to give 1.95 g of 4-nitro-1H-pyrazole-3-carboxylic acid 4-hydroxy-cyclohexylamide. (LC/MS: Rt 1.62, [M+H]+255).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5334-40-7, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77424; (2006); A1;; ; Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77425; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 28466-26-4, 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. 28466-26-4, name is 4-Aminopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

0.2g of compound 2 and 0.11g of 4-aminopyrazole were dissolved in n-butanol. 0.27g of N,N-diisopropylethylamine was added to the solution and was heated at 150C under microwave for 2h. After completion of the reaction, the solvent was evaporated to dryness using a rotary evaporator under reduced pressure to obtain a crude product. The product was purified by column chromatography (dichloromethane:methanol = 20:1) to give 0.15g of compound 3 as a yellow solid, yield: 65%.

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

Reference:
Patent; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 930-36-9, A common heterocyclic compound, 930-36-9, name is 1-Methylpyrazole, molecular formula is C4H6N2, 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.

To a stirred solution of 1 -methyl- lH-pyrazole (609 mmol) in dry ether (600 mL) under an atmosphere of nitrogen is added a solution of n-BuLi in hexane (2.6 M, 670 mmol) dropwise at -78C over a period of Ih. The reaction mixture is then stirred at this temperature for a further 1 h, and then dry carbon dioxide gas is passed through the mixture at -78C for 30 min. The reaction mixture is then allowed to warm to room temperature and quenched with water (500 mL). The aqueous phase is separated, washed with ether (500 mL) and cooled to 2-3 0C. To the stirred mixture is added concentrated aqueous hydrochloric acid until a peta of 3 is obtained. The resulting precipitate is collected by filtration, washed with ice-cold water (20 mL), dried first in open air, and then in a vacuum desiccator over P2O5 to afford 2-methyl-2H-pyrazole-3-carboxylic acid as a white powder.[00249] Compound wt: 35.3g, 45.4% yield. 1H NMR (400 MHz, OMSO-d6) delta: 13.31 (IH, bs);7.50 (IH, d); 6.81 (IH, d); 4.07 (3H, s).

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; Galapagos NV; WO2009/71705; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 151049-87-5, 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. 151049-87-5 name is 3-Bromo-1-methyl-1H-pyrazole, 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.

1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole A mixture of 3-bromo-1-methyl-1H-pyrazole (100 mg, 0.62 mmol), 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (500 mg, 1.52 mmol), K3PO4 (400 mg, 1.88 mmol) and Pd(dtbpf)Cl2 (41 mg, 0.063 mmol) in 1,4-dioxane (2.5 mL) and water (0.5 mL) was stirred at 120 C. for 1 h under microwave irradiation. The mixture was then concentrated in vacuo and the residue purified by Biotage column chromatography (SNAP 25 g column, CH2Cl2/EtOH 100/0->99/1) to give the title compound as a yellow resin (45 mg, 26%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-1-methyl-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; Cancer Research Technology, Ltd.; SCHIEMANN, Kai; BLAGG, Julian; MALLINGER, Aurelie; RINK, Christian; SEJBERG, Jimmy; HONEY, Mark; (139 pag.)US2016/16951; (2016); 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. 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C11H5Cl2F3N4

General procedure: A mixture of compound A (5 mmol) and corresponding benzaldehyde (5 mmol) in 10 mL ethanol was refluxed for 24 hours in a reaction flask wrapped up by silver paper. Upon the reactions completed (monitored by TLC), tawny solids were obtained through suction filtration. The precipitates were washed with ethanol (5 mLx3) and recrystallized from ethanol with 50-84% yields.

The synthetic route of 120068-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Letter; Li, Guanglong; Zhou, Cong; Zhu, Chengchun; He, Lujue; Li, Xiaoyang; Xu, Zhiping; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong; Cheng, Jiagao; Letters in drug design and discovery; vol. 16; 10; (2019); p. 1175 – 1180;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 112758-40-4, These common heterocyclic compound, 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, 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.

PREPARATION 461-(3-Chloro-2-pyridyl)-3-methyl-pyrazole-4-carbaldehyde; To a solution of 3-methyl-pyrazole-4-carbaldehyde (0.5 g, 4.5 mmol) in dry dimethylformamide (15 mL) is added potassium carbonate (2.5 g, 18 mmol,) at room temperature. The reaction mixture is stirred at 40 C. for 30 min and then 1-fluoro-2-chloropyridine (0.77 g, 6 mmol,) is added. The reaction mixture is heated at 70 C. for 16 h. After completion, the reaction mixture is cooled to room temperature, diluted with water and then extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and concentrated under reduce pressure. The crude mixture is purified by chromatography on silica gel eluting with hexane/ethyl acetate (75:25, 65:35) to yield 0.525 g (52%) of the title compound. MS (m/z): 222 (M+1).

The synthetic route of 112758-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; US2011/118251; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3920-50-1, The chemical industry reduces the impact on the environment during synthesis 3920-50-1, name is Pyrazole-3-carboxaldehyde, I believe this compound will play a more active role in future production and life.

The compound (72.0 mg) obtained in Example 43-1 was dissolved in methanol (3.5 ml) and then added with pyrazole-3-carboxaldehyde (24.5 mg) and sodium cyanoborohydride (35.9 mg). The reaction solution was adjusted to pH 5 with the addition of acetic acid, followed by stirring at room temperature for 14 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then extracted with chloroform. Then, the organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. After the solvent had been distilled off, the residue obtained was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining hydrochloride (52.3 mg) of the subject compound as a yellow solid. MS(FAB,Pos.):m/z=486[M+H]+1H-NMR(500MHz,DMSO-d6):delta=0.85(6H,t,J=7.5Hz),1.65(4H,m),2.88(4H,m),3.70(2H,brs),3 .78(2H,brs),4.00(2H,brs),4.10(2H,brs),4.28(2H,brs),6.34(1H,d ,J=2.1Hz),6.65(2H,d,J=8.5Hz),7.21(2H,d,J=8.5Hz),7.32(2H,d,J= 8.3Hz),7.38(2H,d,J=8.3Hz),7.51(2H,s),7.69(1H,d,J=2.1Hz).

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, Pyrazole-3-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 83-10-3, The chemical industry reduces the impact on the environment during synthesis 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

Step 2) 4-(3-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)phenoxy)picolinamide To a suspension of 4-(4-amino-3-chlorophenoxy)picolinamide (191 mg, 0.72 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (168 mg, 0.72 mmol) in DCM (10 mL) was added EDCI (166 mg, 0.86 mmol) and HOAT (20 mg, 0.14 mmol). The reaction was stirred at 46 C. for 6 hours, followed by the addition of 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (32 mg, 0.14 mmol) and EDCI (27 mg, 0.14 mmol). The mixture was further stirred at 46 C. for 13 hours, then cooled to rt and diluted with water (10 mL). The resulted mixture was extracted with ethyl acetate (10 mL*3), and the combined organic phases were washed with brine (10 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=50/1) to give the title compound as a pale yellow solid (160 mg, 46.5%). MS (ESI, pos. ion) m/z: 478.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6): delta (ppm) 2.71 (s, 3H), 3.37 (s, 3H), 7.19 (m, 1H), 7.23 (m, 1H), 7.43 (m, 3H), 7.50 (m, 2H), 7.60 (m, 2H), 7.72 (s, 1H), 8.13 (s,1H), 8.52 (d, J=5.6 Hz, 1H), 8.63 (d, J=9.1 Hz, 1H), 11.19 (s, 1H).

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, 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Wu, Yanjun; Liao, Min; Feng, Yanming; US2015/37280; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics