Category: pyrazoles-derivatives

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. 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-3,5-dimethylpyrazole

General procedure: The corresponding pyrazole and thallium(I) borohydride in the appropriate ratio (see below) were added to a 500 mL Schlenk tube. The tube was closed with a rubber septum and three vacuum/nitrogen cycles were made. The septum was replaced with a reflux condenser fitted with a bubbler on top. The nitrogen flow was stopped and the stirred solid mixture was slowly warmed using an oil bath (fitted with a temperature regulator) until melting of the pyrazole was observed. At this point, evolution of hydrogen should initiate. The mixture was heated at the corresponding temperature for the required period and then cooled to r.t. During the reaction, some of the unreacted pyrazole sublimed and was deposited over the inside surface of the Schlenk tube. A heating gun was used to melt it and return it to the reaction mixture. The reaction mixture solidified during cooling and was dissolved in CHCl3 before filtration through neutral alumina. The alumina was washed with three portions of CHCl3. The resulting solution was submitted to low pressure in a rotary evaporator to remove the solvent, affording a white solid that was further purified by sublimation to remove the remaining pyrazole. The yields depended strongly on the degree of purity of the starting pyrazole: higher yields were obtained in all cases when the pyrazoles were purified by sublimation instead of by recrystallization prior to being employed as reactants. Thalium Hydrotris(3,5-dimethyl-4-bromopyrazol-1-yl)borate (TlTp*,Br) (1) 1H-4-Bromo-3,5-dimethylpyrazole (14 g, 80 mmol) and thallium(I) borohydride (4.4 g, 20 mmol) were used. The pyrazole melted at 170-175 °C and the reaction was heated at 180 °C for 4 h. Unreacted pyrazole was removed by sublimation (130 °C, 2 mbar) until no more pyrazole was collected. TlTp*,Br was obtained as a white solid in 90percent yield (13.5 g of TlTp*,Br). In contrast, when the initial pyrazole was purified by recrystallization from petroleum ether the final yield of 1 decreased significantly (71percent, 10.6 g of TlTp*,Br).1H NMR (500 MHz, CDCl3): delta = 4.76 (br s, 1 H), 2.37 (s, 9 H), 2.27 (s, 9 H). 11B{1H} NMR (160 MHz, CDCl3): delta = ?7.08 (d, JB-H = 96.6 Hz). 13C{1H} NMR (125 MHz, CDCl3): delta = 146.7 (d, JC-Tl = 33.6 Hz), 143.0, 95.6 (d, JC-Tl = 29.0 Hz), 12.5 (d, JC-Tl = 95 Hz), 12.1. Anal. Calcd for C15H19BBr3N6Tl: C, 24.40; H, 2.59; N, 11.38. Found: C, 24.65; H, 2.58; N, 11.25.

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; Olmos, Andrea; Pereira, Ana; Belderrain, Tomas R.; Perez, Pedro J.; Synthesis; vol. 50; 17; (2018); p. 3333 – 3336;,
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 5334-39-4 as follows. Formula: C4H5N3O2

(a) tert-Butyl 3-methyl-4-nitro- 1H-pyrazole- 1-carboxylate or tert-butyl 5-methyl-4- nitro- 1H-pyrazole- 1-carboxylate (A25)Di-tert-butyl dicarbonate (5.15 g, 23.6 mmol) and 4-dimethylaminopyridine (0.481 g, 3.93 mmol) were added to a solution of 3-methyl-4-nitropyrazole (2.50 g, 19.7 mmol)in DCM (100 mL) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was washed with water (100 mL), brine (100 mL), dried (phase separator) and concentrated under reduced pressure. The residue was adsorbed onto Si02 and purified by column chromatography (Biotage Isolera, 2 x 40 g Si02 cartridges, 0-50% EtOAc in petroleum benzine 40-60 00) to give the title compoundA25 as a white solid (2.54 g, 57%). LCMS-D: rt 3.39 mm; no product ion detected.

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 449758-17-2, name is 1-(2-Tetrahydropyranyl)-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 449758-17-2, Computed Properties of C8H12N2O

l-Tetrahydropyran-2-ylpyrazole (5.85 g, 38.44 mmol) was dissolved in THF (35 mL) and cooled to -35 C. n-Butyl lithium (18.5 mL of 2.5 M in hexanes, 46.25 mmol) was added dropwise and the solution was stirred for an additional 1 h at -35 C. Chloro(trimethyl) silane (5.4 mL, 42.55 mmol) was added dropwise and the reaction was allowed to warm to room temperature and stir for 3 h. At this point, 100 mL of a saturated ammonium chloride solution was added and the mixture was extracted with ether. The organics were separated, washed with brine, dried over magnesium sulfate and evaporated. The crude material was purified by silica gel chromatography eluting with 0- 50% ethyl acetate in hexanes to give trimethyl-(2-tetrahydropyran-2-ylpyrazol-3- yl)silane (6.88 g, 80%) as a clear oil. 1H NMR (400 MHz, DMSO-d6) d 7.47 (d, J = 1.6 Hz, 1H), 6.42 (d, J = 1.7 Hz, 1H), 5.30 (dd, J = 9.4, 2.3 Hz, 1H), 3.92 – 3.84 (m, 1H), 3.65 – 3.55 (m, 1H), 2.31 – 2.19 (m, 1H), 2.01 – 1.88 (m, 2H), 1.76 – 1.62 (m, 1H), 1.57 – 1.48 (m, 2H), 0.29 (s, 9H). ESI-MS m/z calc. 224.13449, found 225.3 (M+l)+; Retention time: 0.66 minutes (LC method D).

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; ABELA, Alexander Russell; CLEMENS, Jeremy J.; GROOTENHUIS, Peter Diederik Jan; HADIDA RUAH, Sara Sabina; ISHIHARA, Yoshihiro; KHATUYA, Haripada; MCCARTNEY, Jason; MILLER, Mark Thomas; PIERRE, Fabrice Jean Denis; TRAN, Joe Anh; ZHOU, Jinglan; (227 pag.)WO2019/195739; (2019); 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. 15953-45-4, name is 5-Chloro-3-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 15953-45-4

(b) S-Chloropyrazole-S-carboxylic acidA mixture of 5-chloro-3-methylpyrazole (3.6 mmol; see step (a) above), water (6 mL) and fert-butanol (1.2 mL) was heated to 750C, after which KMnO4 (1.42 g, 9 mmol) was added. The mixture was stirred at 75 C overnight and filtered hot. The solids were washed with boiling water. The combined cooled filtrates were extracted with EtOAc, and the combined extracts washed with NaCl (sat., aq.), dried (MgSO4) and concentrated. The crude solid was recrystallised from EPO EtOAc/hexane/pentane to give the sub-title compound as white crystals (Yield:350 mg (67%)).1H-NMR (DMSO-d6, 400 MHz), delta 13.65 (br s, IH), 6.80 (s, IH)

According to the analysis of related databases, 15953-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOLIPOX AB; WO2007/45868; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 151049-87-5, These common heterocyclic compound, 151049-87-5, name is 3-Bromo-1-methyl-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.

(2,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (6.0 g, 22.2 mmol, 1.0 eq.), 3-bromo-1-methyl-1H-pyrazole (4.29 g, 26.7 mmol, 1.2 eq.), potassium carbonate (6.23 g, 44.4 mmol, 2.0 eq.) and tetrakis(triphenylphosphine)palladium(0) (487 mg, 0.67 mmol, 0.03 eq.) were combined into a reaction flash under an inert atmosphere. Degassed 1,4-dioxane (92.5 mL) and water (18.5 mL) were added. After 16 h at 100 C., the reaction mixture was diluted with water and extracted with IPA/CHCl3 (1:3) (3*). The combined organic extracts were concentrated under reduced pressure. Purification using flash column chromatography on silica gel with 0-70% MeCN/DCM provided the title compound (3.9 g, 78% yield). 1H-NMR (400 MHz, DMSO-d6) 7.77 (d, J=2.3 Hz, 1H), 7.48-7.42 (m, 2H), 6.83 (d, J=2.3 Hz, 1H), 5.22 (t, J=5.6 Hz, 1H), 4.49 (d, J=5.5 Hz, 2H), 3.88 (s, 3H); ES-MS [M+H]+=225.4.

Statistics shows that 3-Bromo-1-methyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 151049-87-5.

Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Conn, P. Jeffrey; Engers, Darren W.; Bender, Aaron M.; US2020/131159; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

146941-72-2, name is 4-Bromo-1-methyl-1H-pyrazol-3-amine, 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. Formula: C4H6BrN3

General procedure: A soln. of amine BB-34 (1 eq) and aldehyde or ketone BB-12 (1.05 to 1.1 eq) in MeOH (2 to 4 mL/mmol) was stirred for 1 h at RT. NaBI-U (1.6 to 2 eq) was added portionwise at 0C and the rxn mixture was stirred at a given temperature for a given time (see Table 52). It was quenched with H2O at 0C and extracted with EtOAc. The combined org. phases were washed with brine, dried over MgSCh and concentrated in vacuo. When necessary, the crude was purified by CC using EtOAc/MeOH

The synthetic route of 146941-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (266 pag.)WO2019/137927; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1151802-23-1, The chemical industry reduces the impact on the environment during synthesis 1151802-23-1, name is 4-Bromo-1-cyclopropyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Bis(pinacolato)diboron (330 mg, 1.3 mmol), NaOAc (262 mg, 3.2 mmol), and Pd(dppf)Cl2-dichloromethane complex (89 mg, O. l lmmol) were combined in a microwave vial. 4-Bromo-l -cyclopropyl- lH-pyrazole and DMF (4 mL) were added and the vial was flushed with argon and sealed. The reaction mixture was heated in a microwave for 60 min at 150 0C. The reaction was diluted with 10 mL water and extracted 3 x 10 mL with EtOAc. The combined organic layers were dried over Na2Stheta4 and concentrated to yield 120 mg of the title compound as a dark oil, m/z 235.4 [M +H]+.

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-Bromo-1-cyclopropyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LEMIEUX, Rene, Marc; BRUNETTE, Steven, Richard; HORAN, Joshua, Courtney; KOWALSKI, Jennifer, A.; LAWLOR, Michael, David; MCKIBBEN, Bryan; MILLER, Craig, Andrew; BARBOSA, Antonio, J.M.; WO2010/141273; (2010); 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. 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

Example 7 : 1 -f N’-bis ( f (2-methyl-2-propanyl)oxy]carbonyU carbamimidovfH- piperidinecarboxylic acid To a solution of piperidine-4-carboxylic acid trifluoroacetate salt (0.20 g, 0.82 mmol) in methanol (10 mL), triethylamine (0.20 mL, 1.6 mmol) and N,N’-bis{[(2- methyl-2-propanyl)oxy]carbonyI}-lH-pyrazole-l-carboximidamide (0.30 g, 0.98 mmol) was added and the reaction mixture stirred at room temperature for 18 h. The solvent was evaporated under reduced pressure and the resulting residue dissolved in ethyl acetate and washed with brine. The organic layer was dried and concentrated to dryness to obtain the title compound (200 mg, 76%) as a white solid. NMR (400 MHz, D SO-i) delta 3.91 (d, 2H), 3.30 (t, 2H), 2.63-2.66 (m, IH), 1.90- 1.96 (m, 2H), 1.67-1.69 (m, 2H), 1.45 (s, 18H).

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; ONO PHARMACEUTICAL CO., LTD; IMAGAWA, Akira; KONDO, Takashi; NISHIYAMA, Taihei; COURTNEY, Steve; YARNOLD, Chris; ICHIHARA, Osamu; FLANAGAN, Stuart; WO2013/174937; (2013); 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. 89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H5ClN2O2S

General procedure: 0.20 mmol of theappropriately substituted sulfonyl chloride was dissolved in dry pyridine (2mL) and 0.24 mmol of5-amino-7-alkyl-2-[(methylcarbamoyl)amino]-1-benzothiophene-3-carboxamide (19a-c)was added to the solution. The reaction mixture was stirred until the startingamine disappeared completely according to TLC analysis (2-3 hours). 1.0 Mhydrochloric acid was added, the precipitate was filtered off, washed withwater and dried on air. The crude product was dissolved in hot THF (80-100 mL)and decolorized with activated charcoal. The mixture was filtered through celite,washed with ethyl acetate (2 x 40 mL), and the filtrate was evaporated underreduced pressure. The residue was solidified under diisopropyl ether, and theprecipitate was filtered off and dried on air.

The synthetic route of 89501-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gyulavari, Pal; Szokol, Balint; Szabadkai, Istvan; Brauswetter, Diana; Banhegyi, Peter; Varga, Attila; Marko, Peter; Boros, Sandor; Illyes, Eszter; Szantai-Kis, Csaba; Kreko, Marcell; Czudor, Zsofia; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 19; (2018); p. 3265 – 3270;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 637336-53-9, 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. 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Isoamyl nitrite (1 .3 ml_, 9.67mmol) was added drop-wise to a suspension of methyl 4- amino-1 -methyl-1 H-pyrazole-3-carboxylate (p70, 1 g, 6.45 mmol), CuBr2 (1 .44 g, 6.45 mmol) and CuBr (924 mg, 6.45 mmol) in MeCN (25 ml_). The resulting mixture was stirred at 80 C for 2 hrs. After cooling to RT the volatiles were evaporated under vacuum and the residue was purified by FC on S1O2 column (eluting from cHex to 40% EtOAc) to afford methyl 4-bromo- 1 -methyl- 1 H-pyrazole-3-carboxylate (p71 , 500 mg, y= 35 %) as brown solid. MS (mlz): 220.9 [MH]+

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, Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; CREMONESI, Susanna; SEMERARO, Teresa; TARSI, Luca; GIBSON, Karl Richard; (116 pag.)WO2019/81939; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics