Month: August 2021

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. 36650-74-5, name is 1H-Pyrazole-3-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H3N3

To a solution of lH-pyrazole-3-carbonitrile (2.00 g, 21.5 mmol) in EtOH (3 ml) was added ethyl (2R)-oxirane- 2-carboxylate (1.0 g, 8.61 mmol) (for synthesis refer to example 5AY) portionwise. Then the mixture was stirred at 90C for 0.5 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by FCC (1 :2 EtOAc / petrol) to give the title compound as a colourless oil. Y = 14 %. NMR (400MHz, chloroform-) delta 7.59 (d, J = 3 Hz, 1H), 6.65 (d, J = 3 Hz, 1H), 4.56 – 4.47 (m, 3H), 4.33 – 4.25 (m, 2H), 1.35 – 1.29 (m, 3H).

The synthetic route of 36650-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NODTHERA LIMITED; BOCK, Mark G.; WATT, Alan Paul; PORTER, Roderick Alan; HARRISON, David; (229 pag.)WO2019/25467; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 866837-96-9,Some common heterocyclic compound, 866837-96-9, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate, molecular formula is C12H13N3O2, 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 -Phenyl-5-(pyridin-2-ylamino)-1 H-pyrazole-3-carboxylic acid; 200mg (0,865 mmol) of 5-Amino-1 -phenyl-1 H-pyrazole-3-carboxylic acid ethyl ester were dissolved in 5 ml DMF and 108mg (0,95 mmol, 1 .1 eq) of 2-Chloropyridine, 620mg (1 ,9mmol, 2,2eq) of Cs2C03, 20mg (0, 1 eq) of palladium(ll)acetate and 60mg of xantphos (0, 12eq) were added and the resulting mixture heated to 100C for 6 hours. The mixture was filtered over a pad of Celite and 2 ml of 1 N NaOH (2mmol, 2,3eq) were added together with 2ml of EtOH. After stirring overnight at RT the crude reaction mixture was subjected to HPLC chromatography delivering 60mg of product. (Yield: 25%)

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

Reference:
Patent; SANOFI; RUF, Sven; SADOWSKI, Thorsten; HORSTICK, Georg; SCHREUDER, Herman; BUNING, Christian; OLPP, Thomas; WIRTH, Klaus; WO2012/101199; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 37718-11-9, 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. 37718-11-9, name is 1H-Pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A) methyl 1H-pyrazol-4-carboxylate A mixture of 1H-pyrazol-4-carboxylic acid (4.00 g) and 4 M hydrogen chloride/methanol solution (150 mL) was stirred overnight at room temperature, and the solvent was evaporated under reduced pressure to give the title compound (5.0 g). 1H NMR (400 MHz, DMSO-d6) delta 3.72 (3H, s), 8.09 (2H, s), 11.62 (1H, s).

The synthetic route of 1H-Pyrazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIKAMI, Satoshi; NAKAMURA, Shinji; ASHIZAWA, Tomoko; SASAKI, Shigekazu; TANIGUCHI, Takahiko; NOMURA, Izumi; KAWASAKI, Masanori; EP2848618; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, molecular formula is C4H5N3O2, 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. COA of Formula: C4H5N3O2

A mixture of 2-(l-methyl-lH-pyrazol-3-yl)ethyl methanesulfonate (600 mg, 2.94 mmol), 3-methyl-4-nitro-lH-pyrazole (373 mg, 2.94 mmol), and Cs2C03 (1.92 g, 5.882 mmol) in DMF (20 ml) was stirred at 100 C for 2 h. H20 (20 ml) was added and the resulting mixture was extracted with EtOAc (20 ml x 3). The organic layers were combined, washed with brine (20 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by prep-TLC eluting with petroleum ether/ethyl acetate (1/1) to afford the title compound (600 mg, 87%) as a white solid. LC-MS (ESI): m/z = 236 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5334-39-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BAKER-GLENN, Charles; BURDICK, Daniel Jon; CHAMBERS, Mark; CHAN, Bryan K.; CHEN, Huifen; ESTRADA, Anthony; SWEENEY, Zachary Kevin; WO2013/164321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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. category: pyrazoles-derivatives

General procedure: A mixture of substituted 3-(2-aryl-2-oxoethylidene)indolin-2-one 1 (1 mmol), 1,3-dimethylurea (2, 1.2 mmol) or 5-amino-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (4, 1 mmol), PTSA·H2O (0.3 mmol), and MeCN (5 mL) was added to a 25 mL flask and reacted at 80 C (monitored by TLC) about 2 h. After completion, the mixture was cooled to r.t. and the precipitate obtained was isolated by filtration and drying. Compounds 3 or 5 were purified by recrystallization (DMF or EtOH).

The synthetic route of 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dai, Lei; Shu, Ping; Wang, Zhansheng; Li, Qingyang; Yu, Qiuyu; Shi, Yanhui; Rong, Liangce; Synthesis; vol. 49; 3; (2017); p. 637 – 646;,
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. 449758-17-2, name is 1-(2-Tetrahydropyranyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 449758-17-2

n-BuLi (2.5 M, 40 mL, 0.016 mol) was added to a solution of 1- (tetrahydro-2H-pyran-2-yl) -1H-pyrazole (2.0 g, 0.013 mol) in anhydrous THF (10 mL) at -78 under nitrogen atmosphere. The resulting mixture was stirred at -78 for 30 min before 2-isopropoxy-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane (2.7 g, 0.014 mol) was added dropwise. After addition, the reaction was held at -78 for 3 h. Excess base was quenched with aqueous HCl solution (1 M, 10 mL) and the mixture was warmed to 25 , then extracted with EtOAc (15 mL ×3) . The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (PE:EtOAc 5:1) to afford the title compound. MS: m/z 279.1 (M + 1) .1H NMR (400 MHz, DMSO-d6) delta 7.51 (s, 1H) , 6.64 (s, 1H) , 5.70 (d, J 8.5 Hz, 1H) , 3.89 (d, J 11.3 Hz, 1H) , 3.48 -3.61 (m, 1H) , 2.20 -2.33 (m, 1H) , 1.83-2.03 (m, 2H) , 1.43-1.69 (m, 3H) , 1.28 (d, J 4.8 Hz, 12H) .

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; MERCK SHARP & DOHME CORP.; COOKE, Andrew J.; PITTS, Daniel; JOHNSON, Adam; BESHORE, Douglas C.; HURZY, Danielle; MITCHELL, Helen; FRALEY, Mark; MCCOMAS, Casey; SCHIRRIPA, Kathy; MERCER, Swati P.; NANDA, Kausik; MENG, Dongfang; WU, Jane; BABAOGLU, Kerim; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (156 pag.)WO2016/54807; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 143426-52-2, 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 143426-52-2 as follows.

To a mixture of methyl 4-ethyl-2-hydroxy-5- ( 4 , 4 , 5, 5- tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate (0.54 g) , l-(4- (chloromethyl) henyl) -lH-pyrazole (0.41 g) , 2 M aqueous sodium carbonate solution (1.76 mL) and DME (20 mL) was addedtetrakis (triphenylphosphine) palladium (0) (0.10 g) under an argon atmosphere at room temperature, and the mixture was stirred at 90C overnight. The reaction mixture was dried over anhydrous sodium sulfate, and the. solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.45 g) .MS: [M+H]+337.0

According to the analysis of related databases, 143426-52-2, the application of this compound in the production field has become more and more popular.

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; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 50877-42-4, name is 1-Benzyl-4-iodo-1H-pyrazole, 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. Quality Control of 1-Benzyl-4-iodo-1H-pyrazole

General procedure: A mixture of K2CO3 (0.552 g, 4.0 mmol), Ph3P (5.3 mg,0.02 mmol) and 10% palladium on charcoal (10.6 mg, 0.01 mmol) in EtOH(10 ml) was stirred gently for 30 min, then the hetaryl halide (1.0 mmol) andterminal acetylene (1.2 mmol) were added. The mixture was stirred gently atreflux for 48 h. The resulting precipitate was filtered through a pad of silica geland the EtOH was evaporated. Pure product was isolated by columnchromatography on silica gel using petroleum ether/EtOAc as eluent

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

Reference:
Article; Arsenyan, Pavel; Rubina, Kira; Vasiljeva, Jelena; Belyakov, Sergey; Tetrahedron Letters; vol. 54; 48; (2013); p. 6524 – 6528;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application 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.

To a solution of crude SB (124.8 mg, 0.314 mmol, theoretical amount) in anhydrous THF (3 mL) was added 4-cyanopyrazole (58.5 mg, 0.628 mmol) followed by potassium carbonate (86.8 mg, 0.628 mmol). The solution was heated at 50 C for 2 hours. Then the solution was diluted with ethyl acetate (200 mL). The resulting solution was washed with brine (2×100 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by reverse phase prep-HPLC to afford desired product (34.6 mg, 0.0845 mmol, two steps overall yield=27%) as a white solid. 1HNMR (400 MHz, CDC13) 5(ppm): 7.86 (IH, s), 7.82 (IH, s), 5.01 (IH, AB), 4.91 (IH, AB), 2.61 (IH, t), 2.16-2.26 (2H, m), 2.04 (IH, m), 1.00-1.90 (21H, m), 0.68 (3H, s). LCMS: rt = 2.26 mm, m/z = 410.2 [M+H]+

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169833; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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: C4H6N2

A solution of potassium permanganate (16.17 g, 102.31 mmol) in water (150 mL) was added to a solution of 3-methylpyrazole (4.2 g, 51.15 mmol) in water (100 mL) and the mixture was refluxed overnight. After cooling to room temperature the insoluble material was removed by filtration. The filtrate was concentrated to 30 mL and 2 N HCl was added until a solid was precipitated. The solid was filtered, washed with cold water and dried in vacuo to yield 1H-pyrazole-3-carboxylic acid (3.1 g, 54percent yield) as a white solid which was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1453-58-3, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Trabanco-Suarez, Andres Avelino; Tresadern, Gary John; Delgado-Jimenez, Francisca; US2013/190318; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics