Tag: M.W:100-200

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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2O2

Preparation of Compound 77 Compound 75 was prepared according to J. Heterocycl. Chem., 2003, 487. Compound 75 (10 g, 71.4 mmol), compound 76 (20 g, 89.2 mmol) and K2CO3 (12.328 g, 89.2 mmol) were dissolved in NMP (60 ml), and the mixture was heated to 80° C. for 2 h. The reaction mixture was allowed to cool and diluted with a mixture of ethyl acetate: water=3:1 (500 ml). The water layer was washed with EtOAc (3.x.100 ml), and the organic layers were dried over Na2SO4, and concentrated in vacuo. The residue was purified on silica gel (PE:EA=100:1 to 20:1) to give compound 77 as yellow oil (2.2 g, 10.9percent). 1H NMR (400 MHz, CDCl3): 0.860 (q, 6H, J=4 Hz), 0.978 (m, 1H), 1.213 (m, 1H), 1.372 (t, 3H, J=7.2 Hz), 1.555 (m, 2H), 2.329 (m, 2H), 3.709 (s, 3H), 4.334 (q, 2H, J=7.2 Hz), 5.907 (q, 1H, J=5.2 Hz), 6.896 (d, 1H, J=2 Hz), 7.587 (d, 1H, J=2 Hz). MS-ESI: m/z=283.1 [M+1]+.

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; INTERMUNE, INC.; US2009/257979; (2009); 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. 13808-62-3, name is 4-Methyl-3-phenyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C10H10N2

Alternative Synthesis for N,N,alpha,4-tetramethyl-3-phenylpyrazole-1-acetamide A mixture of 4-methyl-3-phenylpyrazole (3.65 g., 0.023 mole) N,N-dimethyl-2-chloropropionamide (3.78 g., 0.027 mole) and anhydrous potassium carbonate (4.4 g., 0.032 mole) was heated with stirring at 130 C. for 6 hours. The reaction mixture was cooled and crystallized from 50% aqueous methanol to give 4.5 g. of N,N,alpha,4-tetramethyl-3-phenylpyrazole-1-acetamide as large rods, m.p. 87-89 C.

The synthetic route of 13808-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Upjohn Company; US4072498; (1978); A;,
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

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

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

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

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

These common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, 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. Application In Synthesis of 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide

General procedure: To a solution of 2-aminobenzamide (1.470 mmol, 1.0 eq.) was added to a solution of Terminal Alkyne (1.470 mmol, 1.0 eq.), Tosyl Azide, (1.470 mmol, 1.0eq.), CuI (0.147 mmol, 0.1 eq.), triethylamine (2.941 mmol, 2.0 eq.), in acetonitrile (10 ml) under N2 atmosphere. The mixture was stirred at room temperature for 12 h. After completion of the reaction (as indicated by TLC) the reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (2×25 mL), dried over Na2SO4, concentrated under vacuum to get crude compound which was purified by column chromatography using a mixture of petroleum ether: ethyl acetate to give the desired product as a white solid.

The synthetic route of 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Srishyalam; Devanna; Basaveswara Rao; Mulakayala, Naveen; Tetrahedron Letters; vol. 58; 30; (2017); p. 2889 – 2892;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 16617-46-2, 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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of compound SI (5.0 g, 46.30 mmol) and 2-bromo-l,l- diethoxyethane (10.0 g, 50.90 mmol) in DMF (20 mL) was added K2CO3 (12.78 g, 92.60 mmol) in one portion. The reaction mixture was stirred at 80 °C overnight. After cooling to room temperature, the mixture was poured into ice water and extracted with ethyl acetate (250 mL). The organic layer was washed with brine, dried over anhydrous Na2S04, filtered and then concentrated. The residue was purified by column chromatography on silica gel (petroleum ethenethyl acetate = 100: 1 to 5: 1) to afford compound S2 (9 g, yield 90percent) as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-1H-pyrazole-4-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 52222-73-8, The chemical industry reduces the impact on the environment during synthesis 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of compound 10 (500 mg, 1.03 mmol), 4-methylpyridin-2-ol (168 mg, 1.54 mmol) and K2CO3(283 mg, 2.05 mmol) in DMF (5 mL) was stirred at 80 oC for 10 hoursand then concentrated in vacuo to remove DMF. The residue was diluted withwater and extracted with EtOAc. The organic layer was washed with brine, driedover Na2SO4, filtered and concentrated in vacuo. Theresidue was purified by column chromatography (PE : EtOAc = 1 : 1) to give theproduct of 1r (400 mg, yield: 83%).

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

Reference:
Article; He, Shuwen; Li, Peng; Dai, Xing; McComas, Casey C.; Du, Chunyan; Wang, Ping; Lai, Zhong; Liu, Hong; Yin, Jingjun; Bulger, Paul G.; Dang, Qun; Xiao, Dong; Zorn, Nicolas; Peng, Xuanjia; Nargund, Ravi P.; Palani, Anandan; Tetrahedron Letters; vol. 55; 14; (2014); p. 2212 – 2216;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics