Day: June 11, 2021

Related Products of 10250-64-3,Some common heterocyclic compound, 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, molecular formula is C11H10N2O2, 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.

General procedure: To a solution of 19 (1.2 eq) and HOBt(1.4 eq) in DMF (0.5 M) were added EDCI (1.3 eq) and a solution of 15a-j or 16a-j (1.0 eq) in DMF (0.25 M), Et3N (3.5 eq) at 0 C. The reaction mixture was stirred at room temperature for 24 hours, then diluted in AcOEt. The organic phase was washed with water twice, saturated aqueous NaHCO3 three times, and brine, then dried over Na2SO4,filtered, and concentrated. The residue was purified by flash column chromatography to give intermediates 17a-j and 18a-j.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, its application will become more common.

Reference:
Article; Nakagawa, Hidehiko; Seike, Suguru; Sugimoto, Masatoshi; Ieda, Naoya; Kawaguchi, Mitsuyasu; Suzuki, Takayoshi; Miyata, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 25; 23; (2015); p. 5619 – 5624;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31037-02-2,Some common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H11N3O2, 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.

The acid chloride reaction solution was synthesized in the same manner as in Example 1.75 g of water, 67 g of pyrazole amine, 42 g of sodium carbonate and 5 g of triethylamine were added to 1000 ml, cooled to 0 to 5 C, and acyl chlorideThe reaction solution was controlled at a temperature of 5 to 10 C. The dropwise addition was completed and the reaction was completed for 1 hour. The reaction was completed, the layers were separated and the organic phase was dissolved to obtain a crude product.Add 200g of methanol heated to 50 C dissolved, cooled to 5 C, precipitated the solid, filtered to give the product as a white solid, yield:82%, content: 95%.

The synthetic route of 31037-02-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Fuding Chemical Co., Ltd.; Liu, Dongwei; Cheng, Lizhong; Chang, Qing; Dong, Hailong; Zhu, Ruiyu; Gu, Junkun; (11 pag.)CN106631896; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 152120-54-2, These common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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.

General procedure: Method B. The required amine hydrochloride salt 7 (1.5-6.0 equiv) and pyrazole-1-carboxamide 6a (1.0 equiv) were dissolved in acetonitrile or chloroform (ca. 1 mL per mmol) and triethylamine (twofold excess based on 7) was added drop-wise with stirring, together with anhydrous MgSO4 to dryness. After 16 h the mixture was filtered, evaporated and purified by column chromatography on silica.

The synthetic route of 152120-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Al Shuhaib, Zainab; Davies, Deiniol H.; Dennis, Mark; Evans, Daniel M.; Fletcher, Matthew D.; Franken, Herjan; Hancock, Paul; Hollinshead, Jackie; Jones, Iestyn; Kaehm, Kristina; Murphy, Patrick J.; Nash, Robert; Potter, David; Rowles, Richard; Tetrahedron; vol. 70; 29; (2014); p. 4412 – 4419;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, 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 5334-40-7, category: pyrazoles-derivatives

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).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Nitro-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77428; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5334-43-0, 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. 5334-43-0, name is 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 5-amino-1-phenyl-1H-pyrazole-4-carbonitriles (7-12)(0.01 mol) and 20 mL of formic acid was stirred and allowed to reflux for 12 h. The reaction mixture was poured into 50 mL of ice-cold water. The precipitate was collected by filtration and washed with water to produce 13-18 in 68-89% yield. 1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (13). Yield: 74%.MP:>300 C. IR (cm-1): 3116; 1727; 1660; 1591. 1H NMR (400 MHz,DMSO-d6, TMS, delta in ppm): 8.06-7.39 (m; 5H; HAr); 8.20 (d; 1H;J=3.8 Hz; H6); 8.34 (s; 1H; H3); 12.46 (s; 1H; NH). 13C NMR(100 MHz, DMSO-d6, TMS, delta in ppm): 107.6 (C3a); 121.7 (C2?, C6?);127.1 (C4?); 129.1 (C3?, C5?); 135.9 (C3); 138.2 (C1?); 148.7 (C6); 151.8(C7a); 157.2 (C4). EI [M+1]+ 213.07.

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

Reference:
Article; Feitosa, Livia M.; da Silva, Edson R.; Hoelz, Lucas V.B.; Souza, Danielle L.; Come, Julio A.A.S.S.; Cardoso-Santos, Camila; Batista, Marcos M.; Soeiro, Maria de Nazare C.; Boechat; Pinheiro, Luiz C.S.; Bioorganic and Medicinal Chemistry; vol. 27; 14; (2019); p. 3061 – 3069;,
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 129768-30-5 as follows. category: pyrazoles-derivatives

Example 11; N-(2-ethoxybenzyl)-1-(1-(2-(methylamino)ethyl)piperidin-4-yl)-3-(trifluoromethyl)-1 H-pyrazole-5-carboxamide (98); Step 1 tert-butyl 4-(5-(ethoxycarbonyl)-3-(trifluoromethyl)-1 H-pyrazol-1-yl)piperidine-1- carboxylate (93); [0268] tert-Butyl 4-iodopiperidine-i-carboxylate (5 683, 18 26 mmol, E G Corley et al, JOC, 2004, 69, 5120-5123) in DMF (30 7 ml) was added to a mixture of ethyl 3- (trifluoromethyl)-1 H-pyrazole-5-carboxylate (3 2 g, 15 37 mmol, M -A Plancquaert et al, Tetrahedron, 52, 4383-4396) and potassium carbonate 95 31 g, 38 4 mmol) and the mixture was stirred at 80oC for 16h After cooling, water was added and the mixture was extracted with EtOAc, and the organic extraxts were dried, filtered and concentrated Chromatographic purification of the residue by Biotage (5-20% EtOAc m Hexanes, 25M column) gave compound 93 as colorless oil (2 4 g, 39 9% yield) LFRMS (ESI) calc 391 4, found 414 1 (M+Na)+

According to the analysis of related databases, 129768-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; METHYLGENE INC.; WO2008/104077; (2008); 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 78703-53-4 as follows. Recommanded Product: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

General procedure: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid of formula (III) (7.76 g, 40 mmol)Reflowed with thionyl chloride (47.6 g, 0.4 mol) for 4 hours.When the reaction system turns into a pale yellow transparent liquid,Continue to react for 30 minutes,The reaction stops,After cooling to room temperature, it was distilled under reduced pressure.1,3-dimethyl-1H-pyrazole-4-yl chloride,1,3-Dimethyl-1H-pyrazole-4-yl chloride (2mmol)Add 15ml of dichloromethane,Join(R)-1-phenethyl-1-amine(2.1mmol),Then triethylamine (0.3 g, 3 mmol) was slowly added dropwise at room temperature overnight;TLC (EA: PE=2:1(V)) tracking,After the reaction was completed, it was extracted three times with a dichloromethane/water = 1:1 (V) system.Concentrated organic layer,Extracted with toluene or 75% ethanol,Column chromatography (EA: PE = 2:1 (V)),Obtained (K19)(R)-1,3-dimethyl-N-(1-phenethyl)-1H-pyrazole-4-carboxamide;

According to the analysis of related databases, 78703-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang University of Technology; Jin Tao; Wang Han; Tan Chengxia; Weng Jianquan; Han Liang; Liu Xinghai; (9 pag.)CN109156471; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route 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.

General procedure: A solution of aldehyde (2 mmol), 3-aminopyrazole (1 mmol), and p-toluenesulfonic acid catalyst (20 mol percent) in MeCN (5 mL) was magnetically stirred for 24 h in room temperature. Next TsCH2NC (1 mmol) was added and the reaction mixture was stirred for 24 h in room temperature. After completion of the reaction, which was followed by TLC EtOAc/petroleum ether 4:1, the reaction mixture was filtered, and the precipitate washed with methanol. Finally pure solid product was obtained by column chromatography.

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

Reference:
Article; Rahmati, Abbas; Eskandari-Vashareh, Miranda; Alizadeh-Kouzehrash, Meysam; Tetrahedron; vol. 69; 21; (2013); p. 4199 – 4204;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 143426-52-2, 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. 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of methyl 2-amino-3,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.69 g), 1-(4-(chloromethyl)phenyl)-1H-pyrazole (0.46 g), 2 M aqueous sodium carbonate solution (2.26 mL) and DME (20 mL) was added (1,1-bis(diphenylphosphino)ferrocene)dichloropalladium(II) dichloromethane adduct (0.09 g) under an argon atmosphere and the mixture was stirred at 80 C. overnight. The reaction mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.65 g). MS: [M+H]+ 336.1

The synthetic route of 1-(4-(Chloromethyl)phenyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Sugimoto, Takahiro; Suzuki, Shinkichi; Sakamoto, Hiroki; Yamada, Masami; Nakamura, Minoru; Kamata, Makoto; Shimokawa, Kenichiro; Ogino, Masaki; Kimura, Eiji; Murakami, Masataka; Kojima, Takuto; Yonemori, Jinichi; (63 pag.)US10548899; (2020); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5932-30-9, These common heterocyclic compound, 5932-30-9, name is Ethyl 5-phenyl-1H-pyrazole-3-carboxylate, 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.

The starting material (100 mg, 0.46 mmol) was dissolved in 10 mL of acetone.Add potassium carbonate (190 mg, 1.38 mmol) and potassium iodide (8 mg, 0.046 mmol),Dimethyl sulfate (31.5 mg, 0.25 mmol), refluxing for 4 h,After TLC detects the reaction, it is filtered.The filter cake was washed with 10 mL of ethyl acetate and 10 mL of dichloromethane until no fluorescence.The filtrates were combined and concentrated.Column chromatography purification (petroleum ether: ethyl acetate = 4:1)Yellow solid99mg,Yield 93.4%,

The synthetic route of 5932-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Wang Jinxin; Yang Kan; Zhi Zhuoer; Nong Keyi; (8 pag.)CN109232426; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics