Month: May 2021

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

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

Related Products of 16034-48-3,Some common heterocyclic compound, 16034-48-3, name is 1-Pyrazoleacetic Acid, molecular formula is C5H6N2O2, 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.

[0462] A solution of Example 1G and DIPEA (0.15 M and0.43 M in DMA, respectively, 257 f.LL, 0.04 mmol Example1 G (1.0 equivalent) and0.12 mmol DIPEA (3.0 equivalents)),HATU (0.2 M in DMA, 257 f.LL, 0.052 mmol, 1.3 equivalents),and 2-(1H-pyrazol-1-yl)acetic acid (0.40 Min DMA,121 f.LL, 0.048 mmol, 1.2 equivalents) were aspirated fromtheir respective source vials, mixed through a perfluoroalkoxymixing tube (0 2 mm inner diameter), and loaded intoan injection loop. The reaction segment was injected into theflow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mLinternal volume) set at 100 C., and passed through the reactorat 180 fJ.Lmin- 1 (10 minute residence time). Upon exiting thereactor, the reaction was loaded directly into an injection loopand purified by preparative HPLC on a Phenomenex LunaC8(2) 5 flill 100 A AXIA colunm (50 mmx21.2 mm) Agradient of acetonitrile (A) and 0.1% ammonium acetate inwater (B) was used, at a flow rate of30 mLmin (0-0.5 min 5%A, 0.5-6.5 min linear gradient 5-60% A, 6.5-7.0 min lineargradient 60-100%A, 7.0-8.9 min 100%A, 8.9-9.0minlineargradient 100-5%A, 9.0-10 min 5%A) to yield the title com-pound (7.33 mg, 39% yield). 1H NMR (400 MHz, DMSOd6D20)o7.76 (d, 1=2.3 Hz, lH), 7.60-7.45 (m, 4H), 7.37-7.28 (m, lH), 7.07-6.87 (m, 3H), 6.31 (t, 1=2.1 Hz, lH), 5.82 (s,lH), 5.00 (s, 2H), 3.93 (q, 1=6.9 Hz, 2H), 3.36 (s, 3H), 1.14 (t,1=6.9 Hz, 3H). MS (ESI) m/z 481.1 (M+W).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Pyrazoleacetic Acid, its application will become more common.

Reference:
Patent; Bogdan, Andrew; Kati, Warren M.; McDaniel, Keith F.; Park, Chang H.; Sheppard, George S.; Wang, Le; US2015/158873; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, 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. Safety of 5-Amino-1,3-dimethylpyrazole

General procedure: 3-methyl-1-phenyl-1H-pyrazol-5-amine (1 mmol, 173 mg) and acetophenone (1.5 mmol, 180 mg), CuI (10 mol %, 19 mg) and FeCl3.6H2O (10 mol %, 27 mg) were added in DMSO (2 mL) at 120C in a round-bottom flask equipped with a magnetic stirring bar and a reflux condenser. After completion of the reaction the organic mixture was extracted with ethyl acetate (3×50 mL) and then washed with brine solution. The organic fraction was dried with anhydrous sodium sulphate and concentrated in rotavapor under vacuum. The product was purified by column chromatography using silica gel (100-200 mesh, ethyl acetate/hexane as eluent).

The synthetic route of 5-Amino-1,3-dimethylpyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rastogi, Gaurav K.; Saikia, B-Shriya; Pahari, Pallab; Deb, Mohit L.; Baruah, Pranjal K.; Tetrahedron Letters; vol. 60; 17; (2019); p. 1189 – 1192;,
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. 20583-33-9, name is 1-(1H-Pyrazol-3-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H6N2O

Example 18, Step B[00173] To a solution of compound 18b (31 g, 280 mmol) in CH3CN (500 mL) was added iodine (38 g, 150 mmol) and then eerie ammonium nitrate (164 g, 300 mmol) and the reaction mixture stirred for 24 hours at r.t. A cold solution of 5% aqueous NaHS03 was added to the reaction mixture and the mixture extracted with EtOAc (300 mL><3). The combined organic layers were dried over MgSO-t, filtered and concentrated in vacuo to give product 18c (65 g, 98%) which was used without further purification. According to the analysis of related databases, 20583-33-9, the application of this compound in the production field has become more and more popular. 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

Synthetic Route of 1105039-93-7, A common heterocyclic compound, 1105039-93-7, name is 1-(4-Methoxybenzyl)-1H-pyrazole-4-carboxylic acid, molecular formula is C12H12N2O3, 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.

According to Scheme 3 Step 1: A solution of 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylic acid (34.4 mmol, 8.00 g), oxalyl chloride (68.9 mmol, 5.92 mL) and a drop of DMF in DCM (80 mL) was stirred for 1 hour at room temperature. After evaporation, the crude product was dissolved in DCM (30 mL) and was added at 0 C. to a solution of N,O-dimethylhydroxylamine hydrochloride (103 mmol, 6.31 g) in DCM (100 mL) followed by Et3N (138 mmol, 19.2 mL). The reaction mixture was stirred for 1 hour at room temperature. The reaction was quenched with a saturated solution of Na2CO3 (300 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide (33.8 mmol, 9.30 g, 98%) as a beige solid.LC (Zorbax SB-C18, 3.5 mum, 4.6×50 mm Column): RT=1.78 min; MS m/z ES+=276.

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; Bolea, Christelle; Calanire, Sylvain; US2010/144756; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 41680-34-6, A common heterocyclic compound, 41680-34-6, name is 3-Amino-1H-pyrazole-4-carboxylic acid, molecular formula is C4H5N3O2, 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.

A mixture of 5-amino-i H-pyrazole-4-carboxylic acid (807 mg, 6.35 mmol) and methyl 2,4- dioxopentanoate (i.83 g, i2.7 mmol) in acetic acid (4.9 ml, 86 mmol) was heated for i hat iioC in a microwave reactor. Upon cooling to room temperature, the reaction mixture waspoured into water and the resulting precipitate was filtered off. The residue was washed with methanol to give the title compound (6i 5 mg, 85% purity) together with unknown impurities.[C-MS (Method i): Rt = 0.62 mm; MS (ESIpos): m/z = 236 [M+H]1H-NMR (400 MHz, DMSO-d6) 6 [ppm]: i.906 (2.ii), 2.666 (i6.00), 2.855 (i.3i), 2.857 (i.32), 3.962 (2.ii), 4.003 (i5.5i), 7.570 (5.55), 8.583 (5.25), 8.753 (0.73).

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; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 155600-99-0,Some common heterocyclic compound, 155600-99-0, name is 3,5-Dibromo-1-methyl-4-nitro-1H-pyrazole, molecular formula is C4H3Br2N3O2, 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.

Production example 7 3-bromo-5-(2′-hydroxyethylamino)-1-methyl-4-nitropyrazole 3 g (10.5 mmoles) of 3,5-dibromo-1-methyl-4-nitropyrazole are heated in a solution of 30 ml ethanolamine in 30 ml ethanol for 15 hours at boiling temperature. The reaction mixture is then poured on 200 ml water, the separated product is filtered, washed with water (20 ml) and vacuum dried. Additional product crystallizes from the filtrate when cooled (5 C.). 2.25 g (81 percent of theory) of 3-bromo-5-(2′-hydroxyethyl)amino-1-methyl-4-nitropyrazole are obtained in the form of yellow crystals with a melting point of 150 C. 1 H-NMR (60 MHz, DMSO-d6): =7.38 (s; wide; 1H; –NH; exchangeable with D2 O), 4.98 (s; wide; 1H; –OH; exchangeable with D2 O), 3.82 (s; 3H; N–CH3) and 3.60 ppm (m; 4H; –NH –CH2 –CH2). MS (70 eV):m/e=266 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromo-1-methyl-4-nitro-1H-pyrazole, its application will become more common.

Reference:
Patent; Wella Aktiengesellschat; US5663366; (1997); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 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 25016-11-9, COA of Formula: C5H6N2O

1-Methyl-1H-pyrazole-4-carbaldehyde (11.0 g, 0.1 mol), sodium bromate (6.0 g, 0.04 mol) and 50 g of acetic acid (0.83 mol) were mixed at room temperature. Add 12.5 g of ammonia-containing molecular mass concentration of 25% ammonia water and 100 ml of water. heating to 90 C, the reaction is exothermic, maintaining the reaction temperature of 100 C, refluxing reaction for 1 hour (to 1-methyl-1H-pyrazole-4-carbaldehyde reaction is complete), The reaction solution was cooled to room temperature, poured into ice water and quenched and diluted. neutralize until the reaction solution is neutral, extract with ethyl acetate, and dry. After concentrating the product, it is distilled under reduced pressure and recrystallized.The product obtained was 10.2 g, the yield was 95%, and the purity was over 99%.

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; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (14 pag.)CN108707113; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 154471-65-5, 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. 154471-65-5, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-methyl-5-trifluoromethyl-2H-pyrazole-3-boronic acid: 1-methyl-3-trifluoromethyl-1H-pyrazole (1.00 g, 6.66 mmol) was dissolved in THF (25 mL) in an oven-dried round bottom flask and cooled to-78 C in an acetone/dry ice bath. 2.5 M n-butyl lithium/hexane (3.196 ml, 7.99 mmol) was added drop wise to the stirred solution followed by drop wise addition of triisopropyl borate (5.01 g, 26.64 mmol). The mixture was warmed to room temperature and stirred for three hours. The reaction mixture was adjusted to pH 6 with IN HCl solution followed by the removal of THF under vacuum. The aqueous phase was extracted with EtOAc (3×100 ml). The combined organic phase was washed with brine and dried over anhydrous MgS0(sub>4, filtered and evaporated to give 2-methyl-5-trifluoromethyl-2H-pyrazole-3-boronic acid (1.12 g, 5.80 mmol, 87 % yield) as a white solid: LCMS m/z (%) = 195 (M+H, 100). 1H NMR (400 MHz, DMSO-d₆) delta: 8.37-8.40 (m, 2H), 7.57 (dd, J= 4.0 Hz, 1H), 4.06 (s, 3H).

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, 1-Methyl-3-(trifluoromethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/12254; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics