Tag: M.W:200-300

Electric Literature of 155377-19-8, These common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-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.

Example 122: Preparation of l-difluoromethyl-3-trifluoromethyl-l//-pyrazole-4- carboxylic acid ethyl ester and 2-difluoromethyl-3-trifluoromethyl-2/:/-pyrazole-4- carboxylic acid ethyl esterSodium hydride (60% in mineral oil) (320 mg, 7.93 mmol) was washed with hexane (2x 10 ml) and suspended in tetrahydrofiiran (20 ml) in a three necked flask. 3- Trifluoromethyl-l//-pyrazole-4-carboxylic acid ethyl ester (1.5 g, 7.21 mmol) (prepared according to JP 2000/044541) in tetrahydrofiiran (10 ml) was added dropwise and the solution stirred at room temperature for 30 minutes. Chlorodifluoromethane was bubbled through the solution for 5 minutes and then the mixture was stirred at room temperature for 3 hours, with additional chlorodifluoromethane bubbled through the solution after every hour for 5 minutes. The reaction mixture was stored at room temperature for 16 hours. The reaction mixture was quenched by addition of water and extracted with ethyl acetate. The organic extract was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: 0-25% ethyl acetate in hexane) to give l-difluoromethyl-3-trifluoromethyl- l//-pyrazole-4-carboxylic acid (isomer A) (870 mg, 47% yield) and 2-difluoromethyl-3- trifluoromethyl-2H-pyrazole-4-carboxylic a’cid (isomer B) (500 mg, 27% yield). Isomer A 1H-NMR (400 MHz, CDCl3): 1.37 (t, 3H, Me), 4.37 (q, 2H, CH2), 7.37 (t, IH, CH), S.07 (s, IH, CH) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 1.37 (t, 3H, Me), 4.37 (q, 2H, CH2), 7.22 (t, IH, CH), 8.43 (s, IH, CH) ppm.

Statistics shows that Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate is playing an increasingly important role. we look forward to future research findings about 155377-19-8.

Reference:
Patent; SYNGENTA LIMITED; WO2007/71900; (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. 60061-68-9, name is 4-Bromo-3-methyl-5-(trifluoromethyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Formula: C5H4BrF3N2

Synthesis of 1-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-2-(4-bromo-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone Protocol T was followed using 4-Bromo-5-methyl-3-trifluoromethyl-1H-pyrazole, K2CO3, 2-Chloro-1-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethanone and DMF. Column chromatography using a solvent mixture (hexane/ethyl acetate=2/3) afforded the title compound as white solid. 1H NMR (400 MHz, CDCl3) delta 6.96-7 (m, 2H), 6.84-6.9 (m, 2H), 5 (s, 2H), 3.6-3.8 (m, 4H), 3.02-3.16 (m, 4H), 2.3 (s, 3H). 13C NMR (400 MHz, CDCl3) delta 162.6, 146.5, 142, 118.5, 116, 52.2, 50.4, 46, 42.2, 15.

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; ChemoCentryx, Inc.; US2004/162282; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, 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. Formula: C10H7ClN4

General procedure: Equimolar portionsof the intermediate compounds 1 (1 mmol) and the intermediatecompounds 3 (1 mmol) were dissolved in approximately 8 mL ofethanol. The reaction solution was allowed to stir at 80 8C for 2 huntil the reaction was complete. The reaction was monitored byTLC. Mostly, a precipitate formed and was then collected by suctionfiltration.

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

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Li, Dong-Dong; Ruan, Ban-Feng; Li, Qing-Shan; Chu, Ming-Jie; Ai, Cheng-Ying; Liu, Dao-Hong; Mo, Kai; Cao, Hai-Qun; Chinese Chemical Letters; vol. 28; 2; (2017); p. 377 – 382;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 37687-24-4,Some common heterocyclic compound, 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, molecular formula is C9H12N2O4, 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.

In 250 mL of acetonitrile was dissolved 2-chloro-l-(l -methyl- 1H- pyrazol-4-yl)ethanone (18.3 g, 115 mmol) and diethyl lH-pyrazole-3,5-dicarboxylate (24.5 g, 115 mmol) before finely ground K2CO3 (31.9 g, 231 mmol) was added in one portion. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was filtered, and the cake was washed with acetonitrile (100 mL). The filtrate was concentrated in vacuo to a thick oil. The oil was dissolved in EtOAc (80 mL), and heptane (200 mL) was added slowly with stirring. The resultant solids were stirred for 2 h, then filtered and washed with heptane. The solids were dried in a vacuum oven to afford the title compound (26.4 g, 67% yield).

The synthetic route of 37687-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 39806-90-1, 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 39806-90-1 as follows.

Example 58. Synthesis of (R)-5-(l,4-dimethyl-6-(l-methyl-lH-pyrazol-4-yl)-5,6- dihydro-4H-benzo[b] [l,2,4]triazolo[4,3-d][l,4]diazepin-8-yl)pyridin-2-amine (Compound 76). The title compound was synthesized by the following scheme:[00393] (R)-8-bromo-l,4-dimethyl-6-(l-methyl-lH-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b] [l,2,4]triazolo[4,3-d][l,4]diazepine (Step 1). A mixture of (R)-8-bromo-l,4-dimethyl-5,6- dihydro-4H-benzo[b][l,2,4]triazolo[4,3-d][l,4]diazepine (292 mg, 1 mmol), 4-iodo-l-methyl- lH-pyrazole (312 mg, 1.5 mmol), copper (I) iodide (58 mg, 0.3 mmol), 1,10-phenanthroline (54 mg, 0.3 mmol) and potassium phosphate (424 mg, 2 mmol) in dimethyl sulfoxide (10 mL) was heated at 150C for 14 hours under nitrogen. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (20 mL x 3). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated to give (R)-8-bromo-l,4-dimethyl- 6-(l-methyl-lH-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b] [1,2,4] triazolo[4,3-d][l,4]diazepine which was used in the next step without further purification. LRMS (M+H)+: calcd 372.07; found 372.

According to the analysis of related databases, 39806-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H15N3O2

2D (3.5 g, 16.7 mmol) was dissolved in tetrahydrofuran (35 mL)Cooled to 0 C,60% sodium hydride (1.0 g, 25.4 mmol) was added,After reaction for 30 minutes, methylsulfonyl chloride (2.9 g, 25.4 mmol) was added and reacted for 1 hour.The reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (50 mL x 2). The organic layers were combined and the organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / Ethyl acetate (v / v) = 1: 1) to give 2E as a white solid (2.1 g, yield 44%).

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; ZHANG, CHEN; FAN, JIANG; LEI, MING; WEI, YONG-GANG; (61 pag.)TW2017/8223; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-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 10250-64-3, Recommanded Product: 10250-64-3

(R) -1,1,1-trifluoro-2-((S) -5-methyl-5,6,7,8-tetrahydro [1,2,4] triazolo [4] obtained in the previous step , 3-a] pyrazin-3-yl) propan-2-ol dihydrochloride (39 mg) and 1-methyl-3-phenyl-1H-pyrazole-5-carboxylic acid (29.1 mg) were added to dimethylformamide (0. 6mL). below freezing,To this mixture was added diisopropylethylamine (83 muL) and HATU (55 mg),Stir at room temperature overnight.Under ice-cooling, a saturated aqueous sodium hydrogen carbonate solution and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate.Organic layer with saturated aqueous sodium bicarbonate solution,Washed sequentially with water and saturated aqueous sodium chloride solution. The organic layer was dried with sodium sulfate.Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1 to chloroform: methanol = 20: 1).Add ethyl acetate and hexane to the resulting solid,Stir at room temperature for 1 hour.By filtering the solid,The title compound (41.7 mg) was obtained.

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-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; japan Tobacco Inc.; Maeba, Takaki; Sazawa, Koichi; Kotoku, Masayuki; Masuo, Ritsuki; Motoda, Dai; Yamaoka, Nobutaka; (126 pag.)JP2019/131544; (2019); A;,
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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 1280210-79-8

Synthesis of 244-A. To a solution of tert-butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)- carboxylate (1.40 g, 6.70 mmol) in DCM (10 mL) was added TFA (3 mL) dropwise under ice bath. Then the solution was stirred at room temperature 1 h. The solvent was removed in vacuo to give 244- A as a crude product

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; RODIN THERAPEUTICS, INC; JEFSON, Martin, R.; LOWE, John, A., III; DEY, Fabian; BERGMANN, Andreas; SCHOOP, Andreas; FULLER, Nathan, Oliver; (165 pag.)WO2017/7756; (2017); 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.

Take raw material 1 (0.01mol) and raw material p-aminophenol 2 (0.01mol) was dissolved in DMF 15mL, was addedEDC.HCl (5.75 g, 0.03 mmol) was added and the reaction stirred at room temperature for 8 h. After the reaction was completed, water was added to the reaction solution to precipitate a white solid After stirring for 15 min, the filter cake was washed with water to neutrality and dried in vacuo to give a white solid. Intermediate 3 was obtained in 94% yield.

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; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Jianqi; Huang Daowei; Wang Wenya; Zhang Zhiguo; Jiang Ling; (45 pag.)CN107286140; (2017); 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 141573-95-7 as follows. Computed Properties of C8H10F2N2O2

Preparation Example V.13-difluoromethyl-1-methyl-1H-pyrazol-4-ylcarboxylic acidA mixture of ethyl 3-difluoromethyl-1-methyl-1H-pyrazol-4-ylcarboxylate (1.4 g, 52 mmol) and aqueous sodium hydroxide solution (10% strength, 3.1 g, 8 mmol) was stirred at 60 C. for 2 h. The reaction mixture was cooled to room temperature, and the pH was then adjusted to 1 using concentrated hydrochloric acid. The reaction mixture was cooled further to 0 C., resulting in the precipitation of a solid. The precipitated solid was filtered off, washed with cyclohexane and dried under reduced pressure. This gave 3-difluoromethyl-1-methyl-1H-pyrazol-4-ylcarboxylic acid as a solid (amount: 0.8 g; yield: 87%). 1H-NMR (DMSO-d6): delta=3.9 (s, 2H), 7.2 (t, 1H), 8.35 ppm (s, 1H).

According to the analysis of related databases, 141573-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; US2011/40096; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics