Tag: M.W:200-300

Reference of 2033-45-6, 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. 2033-45-6, name is 3,5-Dimethyl-4-iodopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of pyrazole (2.04g, 0.03mol) in freshly distilled THF (20mL) was added to a stirred suspension of sodium hydride (60%, 2.04g, 0.03mol) in 20mL THF at room temperature. After 1h, Cyanuric chloride (1.85g, 0.01mol) in THF (15mL) was added to the above solution and white precipitate was formed. After being stirred and heating at 70C for 5h, the solution was filtered off, the filtrate evaporated on a steam bath, and then washed with hot-water. 2,4,6-tri(1H-pyrazol-1-yl)methyl)-1,3,5-triazine.

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, 3,5-Dimethyl-4-iodopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Ji-Xiao; Zhu, Zi-Ran; Bai, Feng-Ying; Wang, Xin-Yu; Zhang, Xiao-Xi; Xing, Yong-Heng; Polyhedron; vol. 99; (2015); p. 59 – 70;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

866837-96-9, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-3-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. Safety of Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate

11512] A solution of ethyl 5-amino-i-phenyl-1H-pyra-zole-3-carboxylate (CAS: 866837-96-9, 300 mg, 1.3 mmol) in THF (6.5 mE), under nitrogen atmosphere was cooled down to -78 C. Diisobutylaluminum hydride (1 M in toluene, 2.9 mE, 2.9 mmol) was added dropwise to the solution, and the stirring at -78 C. was continued for 1 hour. Methanol was added, and the reaction mixture was stirred for 30 minutes warming to RT. DCM was added, and the organic phase was washed with water. The organic phase was separated using a phase separator and concentrated under reduced pressure. The titled compound was used as such without any further purification.

The synthetic route of 866837-96-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Akkari, Rhalid; Alvey, Luke Jonathan; Bock, Xavier Marie; Claes, Pieter Isabelle Roger; Cowart, Marlon D.; De Lemos, Elsa; Desroy, Nicolas; Duthion, Beranger; Gfesser, Gregory A.; Gosmini, Romain Luc Marie; Housseman, Christopher Gaetan; Jansen, Koen Karel; Ji, Jianguo; Kym, Philip R.; Lefrancois, Jean-Michel; Mammoliti, Oscar; Menet, Christel Jeanne Marie; Newsome, Gregory John Robert; Palisse, Adeline Marie Elise; Patel, Sachin V; Pizzonero, Mathieu Rafael; Shrestha, Anurupa; Swift, Elizabeth C.; Van der Plas, Steven Emiel; Wang, Xueqing; (454 pag.)US2017/101406; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1280210-79-8, A common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 stirred solution of feri-butyl 2,6-dihydropyriOlo[3,4-c]pyrazole-5(4H)- carboxylate (Step A of Intermediate 7) (35 g, 167 mmol) in DMF (500 mL) at 0 C under N2 was added sodium hexamethyldisilazide in THF (351 mL, 351 mmol) and the mixture was stirred at 0 C for 30 min. Isobutylene oxide (74.3 mL, 836 mmol) was then slowly added. The solution was stirred at 0C for 0.5 h and then stirred at room temperature for 1 h. The solution was heated to 80C for 100 min in a microwave oven, cooled to room temperature and evapoarted under vacuum. The residue was purified by column chromatography on silica gel, eluting with a gradient of 0% to 6% CH2Cl2 MeOH (containing 10% NH4OH) to give a mixture of two regioisomers. The mixture of two regioisomers A and B was resolved by chromatography on a ChiralPak AD-H column eluting with 4-40% MeOH/C02 to give isomer A as the faster eluting isomer and isomer B as the slower eluting isomer. NMR (500 MHz, CD3OD) for isomer B: 57.42 (d, 1H); 4.42 (s, 2H); 4.41 (s, 2H); 4.07 (s, 2H); 1.51 (d, 9H); 1.16 (s, 6H). LC-MS: 226.27 (M+l -56).The desired isomer B was treated with 1 : 1 TF A/CH2CI2 for 1 h to give the title compound. NMR (500 MHz, CD3OD): 67.55 (s, 1H); 4.43 (s, 2H); 4.39 (s, 2H); 4.10 (s, 2H); 1.17 (s, 6H). LC-MS: 182.31 (M+l).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; HICKS, Jacqueline, D.; BIFTU, Tesfaye; CHEN, Ping; QIAN, Xiaoxia; WILKENING, Robert, R.; WO2011/146358; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1222174-92-6, 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. 1222174-92-6, name is Methyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of intermediate 2a (506 mg) in dioxane (10 mL) was treated with LiOH solution (2 M, 1 mL) and the mixture was stirred at 70 C. for 1 h. HCl (1 M) was added and the mixture was extracted with EtOAc. The combined organic layers were dried and the volatiles were removed under reduced pressure to yield the desired compound (84% yield). [0358] LC-MS (Method 2): m/z [M+H]+=205.0 (MW calc.=205.01); Rt=0.31 min.

The synthetic route of Methyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 398495-65-3, name is 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, molecular formula is C13H20N4O4, 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. SDS of cas: 398495-65-3

Step 2. 5-(tert-butyl) 1-ethyl 3-((6-bromo-2-fluoro-3-methoxybenzyl)amino)-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylateSodium triacetoxyborohydride (286.09 mg; 0.136 mmol; 2.00 eq.) was added to a solution of 5-(tert-butyl) 1-ethyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate (200.00 mg; 0.06 mmol; 1.00 eq.) and 6-bromo-2-fluoro-3-methoxybenzaldehyde (157.28 mg; 0.06 mmol; 1.00 eq.) in dichloromethane (4.00 ml), followed by the addition of acetic acid (40.53 mg; 0.06 mmol; 1.00 eq.) and the reaction mix was left stirring at RT. After 1 h no traces of product were seen by LCMS. Some molecular sieves were added to the reaction flask and after 1 h a peak corresponding to the desired product was observed. Reaction mix was left stirring overnight. The reaction was quenched by addition of NaHCO3 solution and extracted twice with DCM. The combined organics were dried over Na2SO4 filtered and concentrated. The crude was purified on silica gel column using 0-100% EtOAc on hexanes to give the desired 5-(tert-butyl) 1-ethyl 3-((6-bromo-2-fluoro-3-methoxybenzyl)amino)-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate (70 mg). MS (M+H)+ found for C21H26BrFN4O5: 513/515.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 398495-65-3, its application will become more common.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); 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. 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 83-10-3

Step 2) N-(5-hydroxypyridin-2-yl)-2,5-dimethyl-3-oxo-1-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide A suspension of 2-amino-5-hydroxypyridine hydrochloride (500 mg, 3.41 mmol) and Et3N (0.77 mL, 5.5 mmol) in DMF (8 mL) was stirred at rt for 1 hour. At the same time, to a solution of 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (0.64 g, 2.75 mmol), HOAT (449 mg, 3.3 mmol) and EDCI (0.63 g, 3.3 mmol) in DMF (8 mL) was added Et3N (0.77 mL, 5.5 mmol) drop wise. The mixture was stirred at rt for 1 hour, followed by the addition of the above prepared mixture. The reaction was heated at 60 C. for 5 hours, then cooled to rt and diluted with water (150 mL). and adjust to pH=6 with HCl (1 M). The mixture was extracted with EtOAc (20 mL*4), and the combined organic phases were washed with brine (20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the title compound as a pale yellow solid (699 mg, 78%). MS (ESI, pos. ion) m/z: 325.1 [M+H]+.

The synthetic route of 83-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Wu, Yanjun; Liao, Min; Feng, Yanming; US2015/37280; (2015); A1;,
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. 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 37687-24-4

A solution of 849 mg (4.00 mmol) diethyl pyrazole-3,5-dicarboxylate and 1.02 g (4.00 mmol) 2-bromo-1-(4-tert-butyl-phenyl)-ethanone in 4 ml acetone is treated with 663 mg (4.80 mmol) potassium carbonate. The resulting suspension is stirred overnight at room temperature. The reaction mixture is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated to give 1-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-1H-pyrazole-3,5-dicarboxylic acid diethyl ester as light yellow foam; HPLC/MS 2.77 (A), [M+H] 387.

According to the analysis of related databases, 37687-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; DORSCH, Dieter; BUCHSTALLER, Hans-Peter; MOINET, Gerard; WEGENER, Ansgar; WO2013/143663; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 497832-99-2, name is 4-Bromo-1-methyl-3-(trifluoromethyl)-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 497832-99-2, SDS of cas: 497832-99-2

a) 6- (1 -Methyl-3- (trifluoromethyl)- 1 H-pyrazol-4-yl)-8 -((2-(trimethylsilyl)ethoxy)methoxy)-3-((2- (trimethylsilyl)ethoxy)methyl)guinazolin-4(3H)-oneA suspension of 4-bromo-1-methyl-3-trifluoromethyl-1H-pyrazole (0.02 g, 0.10 mmol), (6- (4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 8- ((2- (trimethylsilyl)ethoxy)methoxy)-3- ((2- (trimethylsilyl)ethoxy)methyl)quinazolin-4(3H)-one (0.05 g, 0.08 mmol, example 28), bis (diphenylphosphino)feffocene-palladium(II)dichloride (0.01 g, 0.01 mmol), potassiumcarbonate (0.03 g, 0.25 mmol) and water (0.2 ml) in dimethylformamide (1 ml) was stirred insealed tube at 100 C for 2 hours and then at 80 C overnight. Filtration and chromatography (C18 reverse phase HPLC, methanol / water = 40:60 to 100:0) yielded the title compound as white solid (0.005 g, 11 %). MS: mle = 571.6 [M+Hf?.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BISSANTZ, Caterina; BONNAFOUS, Rene; BUETTELMANN, Bernd; JAKOB-ROETNE, Roland; LERNER, Christian; RUDOLPH, Markus; WO2014/102233; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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.

Step 2: Synthesis of N-l-(2-(bromomethvnbenzyl>3-(3-tert-butyl-l-P-tolyl-lH- pyrazoI-S-vDnrea.2-(Bromomethyl)benzaldehyde (0.23 g, 1.15 mmol) was dissolved in toluene (30 mL). 3-te/t-Butyl-l-p-tolyl-lH-pyrazol-5-amine (0.158 g, 0.578 mmol), triethylsilane (0.37 mL, 0.269 g, 2.30 mmol), and trifluoroacetic acid (0.222 mL, 0.341 g, 2.99 mmol) were added. The reaction was stirred at 65 0C for five hours. It was allowed to cool to room temperature. Ethyl acetate (50 mL) was added and it was extracted with NaHCO3 (aq.) (50 mL) and H2O (50 mL). The organic phase was dried over MgSO4, filtered, and evaporated. The crude product was purified by flash column chromatography. The resulting solid was recrystallized from ethyl acetate / hexane. (0.140 g, 53 %). IHNMR (400 MHz5 DMSO-J6) delta ppm 1.22 (s, 9H) 2.33 (s, 3H) 4.35 (d, J=5.64 Hz, 2H) 4.74 (s, 2H) 6.25 (s, IH) 6.95 (t, J=5.50 Hz, IH) 7.15-7.35 (m, 7H) 7.34-7.46 (m, IH) 8.21 (s, IH) HRMS (m/z) 455.1444. M+H, C23H27BrN4O requires 455.1441.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/91176; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 51516-70-2, These common heterocyclic compound, 51516-70-2, name is 5-Amino-1-(4-fluorophenyl)-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: 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 51516-70-2 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