Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, 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 37687-24-4, Product Details of 37687-24-4

In 250 mL of acetonitrile was dissolved 2-chloro-1-(i-methyl-1H- pyrazol-4-yl)ethanone (18.3 g, 115 mmol) and diethyl iH-pyrazole-3,5-dicarboxylate (24.5 g, 115 mmol) before finely ground K2C03 (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 hours, then filtered and washed with heptane. The solids were dried in a vacuum oven to afford diethyl 1-(2-(i-methyl-1H-pyrazol-4- yl)-2-oxoethyl)-1H-pyrazole-3,5-dicarboxylate (26.4 g, 77.4 mmol, 67.1 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 3,5-pyrazoledicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, 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. Product Details of 179692-08-1

Example 15, Step C [00154] To a solution of compound 15c (38 g, 143 mmol) in acetonitrile (380 mL) at r.t. was added K2C03 (39.5 g, 286 mmol) and then PMBCI (24 mL, 177 mmol). The reaction mixture was stirred at 60C overnight. After cooling to r.t., the mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford compound 15d (32 g, 58%).[00155] This compound was characterized by proton NMR (1HNMR) and mass spectroscopy (MS) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): delta 8.13(s, 1 H), 7.23(d, J = 8.8 Hz, 2H), 6.90(d, J = 8.8 Hz, 2H), 5.29(s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H); 1.26(t, J = 6.8 Hz, 3H). Mass spectroscopy indicated MS (ESI): m/z 387 (M+H)+.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

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

Reference:
Article; Cheng, Hua; Wu, Qiong-You; Han, Fan; Yang, Guang-Fu; Chinese Chemical Letters; vol. 25; 5; (2014); p. 705 – 709;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature 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

Adding a certain compound to certain chemical reactions, such as: 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic 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 345637-71-0, Computed Properties of C7H7F3N2O2

A mixture of 5-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2- thiazolyl]tetrahydro-2H-l,2-oxazine (i.e. the product of Step K) (0.235 g, 0.67 mmol), 5- methyl-3-(trifluoromethyl)-lH-pyrazole-l -acetic acid (0.154 g, 0.74 mmol) and N,N-dicyclohexylcarbodiimide (0.152 g, 0.74 mmol) in dichloromethane was stirred at room temperature for 20 h. The reaction mixture was diluted with more dichloromethane and the urea by-product was removed by filtration. The filtrate was concentrated under reduced pressure to a pale-yellow foam (0.42 g). The resulting foam was dissolved in a minimum amount of dichloromethane and loaded onto a chromatotron plate (2mm) eluting with a gradient of ethyl acetate in dichloromethane to give the title compound, a compound of the present invention, as a colourless foamy solid (0.101 g).in NMR (CDCI3): delta 2.05-2.20 (m, 1H), 2.20-2.35 (m, 4H), 3.403.55 (m, 1H), 3.55-3.70 (m, 2H), 3.75-3.88 (m, 1H), 4.08-4.20 (m, 1H), 4.35-4.45 (m, 1H), 4.45-4.55 (m, 1H), 5.08 (s, 2H), 6.02-6.12 (m, 1H), 6.30 (s, 1H), 6.85-6.98 (m, 2H), 7.25-7.38 (m, 1H), 7.72 (s, 1H).

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, 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LIEPA, Andris, Juris; PASTERIS, Robert, James; STEVENSON, Thomas, Martin; WO2011/85170; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 138907-68-3, A common heterocyclic compound, 138907-68-3, name is Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate, molecular formula is C12H12FN3O2, 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: 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 138907-68-3 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

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. 84547-84-2, name is 4-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid

A mixture of 4-bromo- 1 -methyl- 1 H-pyrazole-5-carboxylic acid (5.0 g, 24.4 mmol) and BH3.THF (36.6 mL of a 1 M solution in THF, 36.6 mmol) in THF (50 mL) was stirred at 50 C for 2 days; at this point LCMS showed the completion of the reaction. The reaction was cooled to RT and cautiously quenched with aq. IN HC1 and stirred at RT for 1 h, after which the mixture was extracted with EtOAc (3 X 50 mL). The combined organic extracts were concentrated in vacuo. The residue was chromatographed (80 g Si02; continuous gradient from 0% to 100% EtOAc in hexanes, 25 min) to give the title compound (3.60 g, 18.9 mmol, 77 % yield) as a white solid. LCMS, [M+H]+ = 193.0.

The synthetic route of 84547-84-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; CHENG, Peter Tai Wah; WANG, Ying; (140 pag.)WO2019/126085; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products 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.

5-(3,3-Dimethyl-2-oxo-butylamino)-1 -phenyl-1 H-pyrazole-3-carboxylic acid ethyl ester; O,6g (25,9mmol) of 5-Amino-1 -phenyl-1 H-pyrazole-3-carboxylic acid ethyl ester are dissolved in 50ml DMF, 4,65g (25,9mmol) 1 -bromopinacolone and 16g (49.1 mmol, 1 ,9eq) of Cs2CO3 are added and the resulting mixture is heated to 100C for4hours.The reaction mixture is filtrated and the solvent removed in vacuo, the residue is subjected to preparative HPLC chromatography to obtain 2g (23%) of the product.

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

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., Application In Synthesis of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

Dissolve 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-tert-butyl carboxylate 3a (2.8 g, 13.5 mmol) in acetonitrile (50 mL) and add 3-chloro Benzyl bromide (3.3 g, 16.2 mmol) and cesium carbonate (32.5 g, 47 mmol) were vented 3 times under nitrogen and placed in an 80 C oil bath for 3 hours. The reaction solution was filtered, and the filtrate was concentrated. The residue was purified by column chromatography (petroleum ether: ethyl acetate = 2: 1) to obtain 2-(3-chlorobenzyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-tert-butyl carboxylic acid 3b (4.1 g, yellow oil), yield 91%.

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; Shanghai Meidixi Bio-pharmaceutical Co., Ltd.; Meidixipuya Pharmaceutical (Shanghai) Co., Ltd.; Ren Feng; Wang Xianlian; Xu Yongmei; Chen Chunlin; Cai Jinna; (28 pag.)CN110194773; (2019); A;,
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. 1145-01-3, name is 3,5-Diphenyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1145-01-3

General procedure: A mixture of chalcone (1d) (208 mg, 1.0 mmol) and TsNHNH2 (205 mg, 1.1 mmol) in EtOH (2 mL) were stirred at room temperature for 48 h and then EtOH (2 mL), NaOH (44.0 mg, 1.1 mmol) were added and the mixture was heated at reflux for 15 h, then the solvent was removed under reduced pressure, then CH3CN (4 mL), NaOH (60 mg, 1.5 mmol) and benzyl bromide (255 mg, 1.5 mmol) were subsequently added and the mixture was stirred at room temperature for 2 h. The product was extracted with Et2O and the organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel afforded the desired product 4n as white crystalline solid (276 mg, 89% yield). Mp 114-117 C; deltaH (400 MHz, CDCl3) 5.38 (2H, s), 6.66 (1H, s), 7.09 (2H, d, J 7.2 Hz), 7.21-7.30 (4H, m), 7.32-7.42 (7H, m), 7.87 (2H, d, J 7.2 Hz); deltaC (100 MHz, CDCl3) 53.2, 103.7, 125.6, 126.7, 127.4, 127.6, 128.55, 128.56, 128.6, 128.8, 130.6, 133.4, 137.7, 145.4, 150.9; HRMS (ESI): MH+, found 311.1536. C22H19N2 requires 311.1543, numax (liquid film) 3060, 2955, 2924, 2853, 1452, 1361, 1307 cm-1.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1145-01-3.

Reference:
Article; Tang, Meng; Zhang, Fu-Min; Tetrahedron; vol. 69; 5; (2013); p. 1427 – 1433;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics