Day: June 15, 2021

Application of 175277-11-9, 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. 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

Using General Method A, 3-tert-butyl-1-methyl-1H-pyrazole-5-carboxylic acid (0.054 g, 0.3 mmol), Example A1 (0.1 g, 0.25 mmol), triethylamine (0.76 g, 0.75 mmol) and DPPA (0.137 g, 0.5 mmol) were combined and purified by column chromatography (ethylacetate/hexanes) to afford (4-(4-(4-(3-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)ureido)-3-fluorophenoxy)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate as a white solid (0.115 g, 82% yield). 1H NMR (400 MHz, DMSO-d6): delta 8.89 (s, 1H), 8.84 (s, 1H), 8.68 (s, 1H), 8.50 (d, J=5.6 Hz, 1H), 8.19 (t, J=8.8 Hz, 1H), 7.46 (d, J=2.4 Hz, 1H), 7.33 (dd, J=12.0 Hz, 2.8 Hz, 1H), 7.06 (dd, J=8.8 Hz, 1.6 Hz, 1H), 6.97 (dd, J=5.6 Hz, 2.4 Hz, 1H), 6.35 (s, 2H), 6.07 (s, 1H), 3.60 (s, 3H), 1.19 (s, 9H), 1.10 (s, 9H); MS (ESI) m/z: 565.2 (M+H+).

The chemical industry reduces the impact on the environment during synthesis 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; US2008/261961; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, molecular formula is C7H7F3N2O2, 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. HPLC of Formula: C7H7F3N2O2

To a solution of 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetic acid (2.75 g, 0.013 mol) in N, N-dimethylforamide (22 ml), 1-[bis(dimethylamino)methylene]-1 H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (5.27 g, 0.014 mol), 3-methylsulfanylpiperidine- 4-carbonitrile hydrochloride (2.55 g, 0.013 mol) and triethylamine (5.52 ml, 0.04 mol) at 0C was added and allowed to stirred at room temperature for 3 hrs. After completion of reaction, the reaction mixture was diluted with water extracted with ethyl acetate. The organic layerwas washed with water, brine and dried over sodium sulphate. Organic layer was concentrated to dryness. The residue was washed with diethyl ether afforded 3.5 g of 3-methylsulfanyl-1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]pi peridine-4-carbonitrile.MS: m/z = 347 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 345637-71-0, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; LAMBERTH, Clemens; SULZER-MOSSE, Sarah; CEDERBAUM, Fredrik; UMARYE, Jayant; SONAWANE, Ravindra; WO2013/127808; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference 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 solution of 245 mg (1.19 mmol) of a mixture of 1 -(4-fluorobenzyl)-5-methyl-1 H- pyrazol-4-amine and 1 -(4-fluorobenzyl)-3-methyl-1 H-pyrazol-4-amine (intermediate 1C) in 4.0 mL DMSO was added 453 mg (1.19 mmol) HATU, 0.26 mL N,N- diisopropylethylamine and 200 mg (0.99 mmol) commercially available 2,6- dimethylquinoline-4-carboxylic acid. The reaction mixture was stirred for 20 hours at 25 C. This mixture was directly purified via preparative HPLC (method A1 ) to obtain 92 mg (23%) of the desired title compound together with 208 mg (51%) of the regioisomer N-[1 -(4-fluorobenzyl)-3-methyl-1 H-pyrazol-4-yl]-2,6-dimethylquinoline-4- carboxamide. 1 H NMR (500 MHz, DMSO d6): delta (ppm) = 2.22 (s, 3H), 2.48 (s, 3H), 2.68 (s, 3H), 5.31 (s, 2H), 7.16 – 7.26 (m, 4H), 7.53 (s, 1 H), 7.60 (dd, 1 H), 7.79 (s, 1 H), 7.85 (s, 1 H), 7.89 (d, 1 H), 10.12 (s, 1 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; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHMANN, Bernd; HEISLER, Iring; MUeLLER, Thomas; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (194 pag.)WO2016/12474; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 120068-79-3, A common heterocyclic compound, 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, molecular formula is C11H5Cl2F3N4, 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.

4. Add CF3SOCl to the appropriate reagent, react, heat up, and then add 99.5% of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole. And a mixture of p-toluenesulfonic acid dimethylamine salt, while adding a catalyst, and reacting for 10 hours, the solvent was evaporated under reduced pressure to obtain 98-99% of fipronil.

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

Reference:
Patent; Jiangsu Tuoqiu Agrochemical Co., Ltd.; Shan Xiaojun; Chen Yunshan; Xu Lidong; Liao Dazhang; (4 pag.)CN104557713; (2018); B;,
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. 3469-69-0, name is 4-Iodopyrazole, A new synthetic method of this compound is introduced below., name: 4-Iodopyrazole

4-iodopyrazole (20 g) and ethanol (100 ml) were added and stirred uniformly. KOH (11.6 g) and KI (0.9 g) were added and the methyl chloride gas was introduced into the liquid surface, Control temperature 30_45 C, GC tracking reaction end, add water 100g, dichloromethane extraction (40gX3), Concentrated to no flow liquid, with n-heptane 6ml beating, suction filter white solid, dry, weighing 17.2g, GC purity 98%, yield 80%;

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; Dalian AllyChem Co.,Ltd(AllyChem); WANG, XIANXUE; ZHENG, PENG; (7 pag.)CN103601749; (2016); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 1453-58-3, name is 3-Methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Methylpyrazole

250 mL of dimethyl sulfoxide and sodium hydride 24.0 g (60percent, petroleum ether washing) were added to a three-necked flask, and 41.0 g of 3-methylpyrazole was dissolved in 150 mL of dimethyl sulfoxide, and slowly added to the reaction flask. The reaction was carried out until no bubbles were evolved, and 101.5 g of p-methoxybenzyl bromide was added to maintain the temperature of the reaction system at 30 °C. After the reaction was completed, 1 L of ice water was added, and dichloromethane (200 mL × 3) was added, and the organic phase was combined, washed with water, washed with saturated sodium hydrogen carbonate, brine, and dried over anhydrous sodium sulfate.Concentration gave 99.6 g (98.5percent) of 1-(4′-methoxybenzyl)-3-methylpyrazole.

According to the analysis of related databases, 1453-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nantong University; Tang Yanfeng; Ding Xinyu; Shan Jiahui; Yu Hongmei; Wang Shuqing; Mao Jiarong; Guo Xiaoqing; (5 pag.)CN103880749; (2019); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 449758-17-2, name is 1-(2-Tetrahydropyranyl)-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 449758-17-2, name: 1-(2-Tetrahydropyranyl)-1H-pyrazole

To a solution of 1 -tetrahydropyran-2-ylpyrazole (762 mg, 5 mmol, 1 equiv.) intetrahydrofuran (35 ml) cooled at -78C is added n-butyllithium (2.5M in hexanes) (2.2ml, 5.5 mmol, 1.1 equiv.) dropwise. The mixture is warmed to 0C for 10 minutes and then is warmed to ambient temperature for 10 minutes. It is cooled to -78C and a solution of 2-oxo-3 -(2-trimethylsilylethoxymethyl)- 1,3 -benzothiazole-6-carbaldehyde (1.55 g, 5 mmol, 1 equiv.) in tetrahydrofuran (7 ml) is added. The mixture is stirred at -78C for one hour, quenched with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The extracts are dried over sodium sulfate, filtered, and concentrated to an oil which is purified by silica chromatography eluting with 0-45% ethyl acetate in hexanes to afford 6- [hydroxy-(1 -tetrahydropyran-2-ylpyrazol-3 -yl)methyl] -3-(2- trimethylsilylethoxymethyl)-1,3-benzothiazol-2-one (1 .99g, 4.31 mmol, 86%) as amixture of diastereomers. LCMS (low pH): r.t. 2.27 mm.

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-(2-Tetrahydropyranyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; GARDINIER, Kevin Matthew; GERNERT, Douglas Linn; HAHN, Patric James; HOLLINSHEAD, Sean Patrick; KHILEVICH, Albert; MAYHUGH, Daniel Ray; ORNSTEIN, Paul Leslie; PORTER, Warren Jaye; REEL, Jon Kevin; SCHKERYANTZ, Jeffrey Michael; SPINAZZE, Patrick Gianpietro; STEVENS, Freddie Craig; WITKIN, Jeffrey Michael; (199 pag.)WO2015/183673; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 31108-57-3, These common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, 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: The appropriate carboxylic acid (1.0 equiv) was treated with oxalyl chloridie (1.1 equiv) in CH2Cl2 (0.5 M) at 0 C. The reaction mixture was stirred at room temperature for 1 h. The solvent was removed under N2 and the acid chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate pyrazole (1.0 equiv) was dissolved in CH2Cl2 and cooled to 0 C. The acid chloride was added dropwise and the reaction mixture was stirred at room temperature for 3 h. The mixture was diluted withEtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude product that was purified by flash chromatography(SiO2).

Statistics shows that 1H-Pyrazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 31108-57-3.

Reference:
Article; Otrubova, Katerina; Srinivasan, Venkat; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3807 – 3813;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, 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. Safety of 5-Amino-1,3-dimethylpyrazole

The aldehyde derivative (0.1 mmol, 1.0 eq.) and the required amine (1.3 eq.) are dissolved in 95:5 MeOH/NMP (0.5 mL) in a glass vial, under inert atmosphere (N2) and treated with AcOH (2.0 eq.) and NaBH3CN (1.5 eq.). The reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is concentrated under reduced pressure. Purification of the residue gives the desired product. Starting from the compound of Preparation Q and 1,3 -dimethyl- lH-pyrazol-5 -amine and proceeding in analogy to Procedure Y, the title compound was obtained, after purification by prep-HPLC (basic conditions), as an amorphous solid (11% yield).MS (ESI, m/z): 339.09 [M+H+].

The synthetic route of 3524-32-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (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. 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 51516-67-7

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

The synthetic route of 51516-67-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics