Month: August 2021

Application of 152120-54-2, These common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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: N,N-diBoc-1H-pirazole-1-carboxamidine (0.8 g, 1eq) was dissolved in anhydrous THF (10 mL), then triphenylphosphine (1.01 g, 1.5eq) and the appropriate alcohol (1.3 eq) were. The mixture was then cooled to 0 C and DIAD (0.76 mL, 1.5eq) was added dropwise. The temperature was raised to reflux and stirred overnight. The reaction was quenched with H2O and extracted with CH2Cl2 (3 x 30 mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were purified by flash column chromatography (SiO2) using 1:9 AcOEt / Petroleum ether as the eluent to yield the guanilated agent.

Statistics shows that tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate is playing an increasingly important role. we look forward to future research findings about 152120-54-2.

Reference:
Article; Maccari, Giorgio; Sanfilippo, Stefania; De Luca, Filomena; Deodato, Davide; Casian, Alexandru; Dasso Lang, Maria Chiara; Zamperini, Claudio; Dreassi, Elena; Rossolini, Gian Maria; Docquier, Jean-Denis; Botta, Maurizio; Bioorganic and Medicinal Chemistry Letters; vol. 24; 23; (2014); p. 5525 – 5529;,
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 113100-53-1 as follows. Recommanded Product: 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

General procedure: To a solution of carboxylic acid (1 equiv) in CH2Cl2 or DMF (1 mL) was added HOBt (1.2 equiv) and DIEA (2 equiv). After the mixture was stirred at room temperature for 5 min, EDCI (1.1 equiv) and corresponding amine (1.3 equiv) were added. The mixture was stirred overnight, diluted with ethyl acetate (40 mL), washed with 1 N HCl (10 mL), saturated NaHCO3 (20 mL), H2O (20 mL), brine (20 mL), dried over Na2SO4, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel.

According to the analysis of related databases, 113100-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cheng, Gang; Muench, Stephen P.; Zhou, Ying; Afanador, Gustavo A.; Mui, Ernest J.; Fomovska, Alina; Lai, Bo Shiun; Prigge, Sean T.; Woods, Stuart; Roberts, Craig W.; Hickman, Mark R.; Lee, Patty J.; Leed, Susan E.; Auschwitz, Jennifer M.; Rice, David W.; McLeod, Rima; Bioorganic and Medicinal Chemistry Letters; vol. 23; 7; (2013); p. 2035 – 2043;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

288-13-1, name is 1H-Pyrazole, 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. Recommanded Product: 288-13-1

Step 1 1-Isopropyl-1H-pyrazole To a suspension of NaH (14 g, 0.35 mol 60% in mineral oil) in DMF (120 mL) was added dropwise of a solution of pyrazole (20 g, 0.29 mol) in DMF (30 mL) at C. After addition, the suspension was stirred for 1 hour at room temperature. Isopropyl bromide (53.4 g, 0.44 mol) was added dropwise, and the reaction mixture was stirred at room temperature for 2 hours. Water was added to quench the reaction and the mixture was extracted with diethyl ether. The combined ether layers were washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was distilled under vacuum to afford 1-isopropyl-1H-pyrazole as a colorless liquid (15.0 g, 46.4%).

The synthetic route of 288-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2009/170873; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H6F2N2O2, 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: C6H6F2N2O2

To a 200 ml single-neck round bottom flask was added 28.39 mmol 3 dissolved in 40 ml of dichloromethane, and then 31.32 mmol of triethylamine was added. Stir for 10 minutes; Further adding 31.23 mmol of EDCI and catalytic amount of DMAP to the reaction. Stir at room temperature for 30 minutes. Finally, 28.39 mmol of N,O-dimethylhydroxylamine hydrochloride was added to the system. Stir at room temperature overnight, after the reaction is completed, The mixture was suction filtered under reduced pressure and the filtrate was concentrated to remove solvent. It was dissolved in 20 ml of dichloromethane and diluted. Wash once with 30 ml of water, separate the aqueous layer and extract twice with dichloromethane (10 ml × 2). The combined organic layers were washed once with 20 ml of saturated sodium chloride solution. The aqueous layer was separated and extracted twice with dichloromethane (10 mL×2). The combined organic layers were dried over anhydrous sodium sulfate; The filtrate is concentrated to remove the solvent.With petroleum ether / ethyl acetate (2:1, volume / volume) purification by column chromatography to give a white solid 6; yield 91%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 176969-34-9, its application will become more common.

Reference:
Patent; Nankai University; Fan Zhijin; Yu Bin; Yang Dongyan; Zhao Bin; Guo Xiaofeng; Zhang Nailou; Hao Zesheng; Wu Qifan; Zhou Shuang; Cao Lixin; (36 pag.)CN110128419; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 942853-22-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 942853-22-7 name is 1-(2,2,2-Trifluoroethyl)-1H-pyrazole-3-carboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Compound 1029; Starting material Ai (45 mg, 0.056 mmol) is dissolved in 4 N HCI/dioxane and the reaction mixture is for 1 h at RT. The reaction mixture is concentrated in vacuo to give crude Ci. The acid R2i is dissolved in DMF (2.0 mL), DIPEA (0.059 mL, 0.338 mmol) and TBTU (21 .7 mg, 0.068 mmol) are added. The reaction mixture is stirred for 15 mins. The crude Ci is added and the reaction mixture is stirred at RT for 16 h. The reaction mixture is purified by prep HPLC to provide compound 1029. FIA M.S.(electrospray) : 874.4 (M+H)+ Retention time (min) = 6.0 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1 H) , 8.92 (s, 1 H), 7.95 (b, 1 H), 7.93 (d, 1 H, J = 2.3 Hz), 7.86 (d, 1 H, J = 9.0 Hz), 7.08 (d, 1 H, J = 9.4 Hz), 6.74 (d, 1 H, J = 2.3 Hz), 6.40 (s, 1 H), 5.60 (b, 1 H), 5.44 (m, 1 H), 5.23 (q, 2H, J = 9.3 Hz), 5.09 (b, 1 H), 4.63 (b, 1 H), 4.47 (q, 2H, J = 6.9 Hz), 4.43 (b, 2H), 4.04 (b, 1 H), 3.87 (s, 3H), 2.67-2.65 (m, 1 H), 2.43 (s, 3H), 2.38-2.32 (m, 3H), 2.01 -1 .80 (m, 2H), 1 .58-1 .51 (m, 3H), 1 .44-1 .23 (m, 1 1 H), 1 .39 (t, 3H, J = 7.0 Hz), 0.85 (b, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2,2,2-Trifluoroethyl)-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET , Montse; BORDELEAU, Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63502; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 106368-32-5, A common heterocyclic compound, 106368-32-5, name is 5-Amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazole-4-carbonitrile, molecular formula is C11H10N4O2S, 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: A mixture of 5-amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazol-4-carbonitrile 5 (1.113 g, 5 mmol), the appropriate aldehyde (6, 5 mmol), and few drops of ethanol was added to morpholinium hydrogen sulphate (7, 0.4 g, 2 mmol). The mixture was heated in an oil bath for 5 h at 100 C. After completion of the reaction which was monitored by TLC, the solid product was filtered and crystallized from ethanol.

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:
Article; Abdellatif, Khaled R.A.; Elsaady, Mohammed T.; Abdel-Aziz, Salah A.; AbuSabah, Ahmed H.A.; Letters in drug design and discovery; vol. 14; 8; (2017); p. 930 – 937;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 741717-63-5, 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. 741717-63-5, name is Ethyl 1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl l-phenyl-3- (trifluoromethyl) -IH- pyrazole-4-carboxylate (0.800 g, 2.81 mmol) in EtOH (20 mL) and THF (5 mL) was added 2M aqueous sodium hydroxide (1.69 mL, 8.44 mmol) . The mixture was heated to reflux until TLC indicated completion, cooled to room temperature, and concentrated in vacuo. The residue was dissolved in water and washed with ether. The aqueous layer was then adjusted to pH~4 with 10% HCl. The solid was collected by filtration and dried under vacuum to give l-phenyl-3- (trifluoromethyl) -lH-pyrazole- 4-carboxylic acid (0.560 g, 78%) as a white powder: 1H NMR (400 MHz, DMSO-d6) delta 7.47 (m, IH), 7.58 (m, 2H), 7.94 (m, 2H), 9.24 (bs, IH); m/z (APCI neg) 254.9 (100%) [M-H] .

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11130; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, 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 31108-57-3, Computed Properties of C4H3N3

In a nitrogen-purged glove box, (oxybis(2,1-phenylene))bis(diphenylphosphine) (1.0 g, 1.86 mmol) and toluene (20 mL) were added to a glass jar, containing a TEFLON coated stir bar. A solution of mesitylcopper(I) (0.34 g, 1.86 mmol), in toluene (10 mL), was then added, while stirring. After a few minutes, 4-cyanopyrazole (0.17 g, 1.81 mmol) was added, the jar was capped, and the resulting mixture was stirred at 60C for 3 hours. After cooling to room temperature, the milky white mixture was concentrated, and further dried under vacuum for one hour at 110C. The resulting white solid (0.78 g) was isolated. A PMMA film of this complex did not show emission upon UV-excitation.

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; DOW GLOBAL TECHNOLOGIES LLC; LAITAR, David S.; CLARK, Thomas P.; RACHFORD, Aaron A.; MUKHOPADHYAY, Sukrit; DE VRIES, Timothy S.; DEVORE, David D.; (31 pag.)WO2016/57441; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1310350-99-2, 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. 1310350-99-2, name is 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

d) 4-Chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid methoxy-methyl-amide A solution of 4-chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid (150 mg, 0.76 mmole) in dichloromethane (5 ml) was subsequently treated at 23 C. with N,O-dimethylhydroxylamine hydrochloride (78 mg, 0.80 mmole), N-methylmorpholine (0.09 ml, 0.8 mmole) and EDCI.HCl (154 mg, 0.8 mmole) and stiffing was continued for 16 h. The mixture was washed with 1 M aqueous HCl and H2O, the organic layer was dried, evaporated and the residue purified by chromatography on silica gel using cyclohexane/AcOEt (2:1) to give the title compound (164 mg) as a colorless oil. MS: m/z=240.1 [M]+.

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-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gabellieri, Emanuele; Guba, Wolfgang; Hilpert, Hans; Mauser, Harald; Mayweg, Alexander V.; Rogers-Evans, Mark; Rombach, Didier; Thomas, Andrew; Woltering, Thomas; Wostl, Wolfgang; US2012/238548; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 37687-18-6, These common heterocyclic compound, 37687-18-6, name is 1-(1-Methyl-1h-pyrazol-4-yl)-ethanone, 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.

B. Synthesis of 2-bromo-1-(1-methyl-1H-pyrazol-4-yl)ethanone A solution of 1-(1-methyl-1H-pyrazol-4-yl)ethanone (28.5 g, 230 mmol) in dichloromethane (400 mL) was diluted with absolute ethanol (100 mL) and treated portion-wise with pyridinium tribromide (95%, 77.3 g, 230 mmol). The reaction was stirred at room temperature for 3 hours, during which time it solidified; the mixture was diluted with dichloromethane (300 mL) and water (400 mL), treated with sodium sulfite (5 g) and stirred for 10 minutes. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with water (200 mL), collected by filtration, washed again with water, and dried to afford the product as an off-white solid. Yield: 41.6 g, 205 mmol, 89%. 1H NMR (500 MHz, CDCl3) delta 7.97-7.98 (m, 1H), 7.95 (br s, 1H), 4.17 (s, 2H), 3.95-3.96 (m, 3H).

Statistics shows that 1-(1-Methyl-1h-pyrazol-4-yl)-ethanone is playing an increasingly important role. we look forward to future research findings about 37687-18-6.

Reference:
Patent; Pfizer Inc.; US2012/214791; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics