Category: pyrazoles-derivatives

Related Products of 78208-72-7,Some common heterocyclic compound, 78208-72-7, name is Ethyl 3-isopropyl-1H-pyrazole-5-carboxylate, molecular formula is C9H14N2O2, 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.

NaH (1.23 g, 31.15 mmol) was dissolved in DMF (200 mL) under 2 atmosphere at 0 °C. To this solution was added ethyl 5-isopropylpyrazole-3-carboxylate (5.16 g, 28.33 mmol) in DMF (50 mL) over 10 min at 0 °C. After the addition, the r.m. was stirred for 10 min at 0 °C and then at r.t. for 40 min. 2,2,2-Trifluoroethyl trifluoromethanesulfonate (4.5 mL, 31.15 mmol) was subsequently added and the mixture was stirred at r.t. for 3 h. After this time the rm was quenched by addition of EtOH at 0 °C. Water was added to the mixture and the water layer was extracted with EtOAc. The organic layer was then washed with brine, dried (MgS04), filtered and concentrated in vacuo. The resulting crude was purified by flash column chromatography (silica; heptanes/EtOAc 100/0 to 60/40) to afford intermediate 42 (4.05 g, 54percent) and regioisomer intermediate 43 (1.52 g, 20percent).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BISCHOFF, Francois, Paul; VELTER, Adriana, Ingrid; ROMBOUTS, Frederik, Jan, Rita; DE CLEYN, Michel, Anna, Jozef; VAN BRANDT, Sven, Franciscus, Anna; GIJSEN, Henricus, Jacobus, Maria; ZAVATTARO, Chiara; VAN DEN KEYBUS, Frans, Alfons, Maria; WO2014/111457; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 132712-71-1, 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 132712-71-1 as follows.

General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95%, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol %) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.

According to the analysis of related databases, 132712-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Khot, Supriya S.; Anbhule, Prashant V.; Desai, Uday V.; Wadgaonkar, Prakash P.; Comptes Rendus Chimie; vol. 21; 9; (2018); p. 814 – 821;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 31108-57-3,Some common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, molecular formula is C4H3N3, 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 solution of I-BA10 (20 mg, 0.047 mmol) in acetone (2 mL) were added K2C03 (13 mg, 0.1 mmol) and lH-pyrazole-4-carbonitrile (9 mg, 0.1 mmol) at l5C. The reaction mixture was stirred for lh at l5C. The reaction mixture was filtered and the mother liquor was concentrated. The residue was purified by flash column (0-30% of EtOAc in PE) to give I- BA11 (10.3 mg, 50%) as a solid. (2459) The structure was confirmed by NOE. (2460) 1H NMR (400 MHz, CDCl3) dH 7.86 (s, 1H), 7.81 (s, 1H), 5.10-4.90 (m, 2H), 2.60 (d, J= 8.8 Hz, 1H), 2.00-1.58 (m, 12H), 1.51-1.28 (m, 11H), 1.26 (s, 3H), 1.24-1.12 (m, 2H), 1.10 (s, 3H), 1.08-0.85 (m, 3H); MS ESI calcd. for C27H38N30 [M+H-H20]+ 420, found 420

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (646 pag.)WO2019/126761; (2019); 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., Quality Control of 1-Methyl-1H-pyrazole-3-sulfonyl chloride

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 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; 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

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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 4-Bromo-3-methylpyrazole

A mixture of 4-bro mo-3- methyl-i H-pyrazole (2 g, 12.5 mmol), 2-iodopropane (6.37 g, 37.5 mmol), C52CO3 (6.25 g, 50 mmol) and acetonitrile (30 mL) was stirred at 90 C for 12 h. The reaction mixture was filtered with MeOH (15 ml) and the filtrate was concentrated.The residue waspurified by flash chromatography on silica gel (UV214, PE:DMC = 100:1 to 50:50) to afford the title compound (700 mg, 56%) as a clear oil. LC-MS: [M+H] = 203.1.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (148 pag.)WO2017/221100; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 2075-45-8,Some common heterocyclic compound, 2075-45-8, name is 4-Bromo-1H-pyrazole, molecular formula is C3H3BrN2, 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 sealable vessel was charged with potassium carbonate (3.76 g, 27.2 mmol), 4-bromo- lH-pyrazole (4.00 g, 27.2 mmol), and 10 mL DMF. To this mixture, 2-iodopropane (3.27 ml, 32.7 mmol) was added and the vessel sealed. The mixture was heated at 80 C for 16 h and allowed to cool to rt . The mixture was diluted with EtOAc, extracted with water, water, sat NaHCO3, and the organic layer dried over Na2SO4, filtered and evaporated. The mixture was purified via flash chromatography using a EtOAc in CH2C12 gradient. The desired compound (as determined by TLC, 12 stain) was collected as a colorless liquid.

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

Reference:
Patent; AMGEN INC.; WO2008/8539; (2008); A2;,
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. 16078-71-0, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C12H13N3O2

B. 5-Bromo-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester To a solution of 20.0 g of 5-amino-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester and 10 ml of bromine in 200 ml of chloroform was added 15.8 g of isoamyl nitrite dropwise. The reaction mixture was allowed to stir at room temperature for about 24 hours and the volatiles were removed under reduced pressure. The residue was recrystallized from ethanol/water to provide 10.0 g of 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester. Yield 38%. mp=86-89 C.

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 16078-71-0.

Reference:
Patent; Eli Lilly and Company; US4620865; (1986); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5932-27-4, The chemical industry reduces the impact on the environment during synthesis 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

To a solution of compound G26 (500 mg, 966.07 umol) and compound H22(271 mg, 1.93 mmol) in DML (10 mL) was added CS2CO3 (630 mg, 1.93 mmol). The resulting mixture was heated at 30-40 C and stirred for 16 hr to give yellow solution. LCMS showed the reaction was completed. The mixture was filtered and was partitioned between EtOAc (50 mL). The aqueous layer was extracted with EtOAc (50 mL * 3). The organic layer was washed with saturated brine (50 mL), dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure to give the crude product as a yellow oil. The crude product was purified by combi flash to give compound H23 (490 mg) as a yellow oil.

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, Ethyl 1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; QURIENT CO., LTD.; LEAD DISCOVERY CENTER GMBH; NAM, Kiyean; KIM, Jaeseung; JEON, Yeejin; YU, Donghoon; SEO, Mooyoung; PARK, Dongsik; EICKHOFF, Jan; ZISCHINSKY, Gunther; KOCH, Uwe; (138 pag.)WO2019/197546; (2019); 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. 1453-58-3, name is 3-Methylpyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Methylpyrazole

A stirred solution of 3-methylpyrazole (82.1 g, 1.0 mol) in water (3.5 L) was heated to 70 °C. Potassium permanganate (111 g, 0.70 mol) was added in one portion, keeping the temperature near 70 °C. The reaction mixture was stirred for 1 h at 70 °C, and then a second portion of potassium permanganate (111 g) was added at 70 °C. After 1 h, a final portion of potassium permanganate (111 g) was added at 70 °C. The reaction mixture was stirred a further 2 h at 70 °C, and any unreacted oxidant was reduced by the dropwise addition of isopropanol. The reaction mixture was cooled to room temperature, filtered, the solid was rinsed with water, and the filtrate evaporated to 500 mL. The aqueous was chilled to 0 °C, acidified with concentrated HC1, filtered, the solid product washed with water, and dried under vacuum to provide pyrazole- 3-carboxylic acid as a white solid (64.4 g, 57percent). Dimethyl sulfate (236 g, 177 ML, 1.87 mol) was added dropwise over 45 min to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) in 20percent aqueous sodium hydroxide (850 ML) at 40 °C. The reaction mixture was heated at 80 °C for 2 h, cooled to room temperature, filtered, the filtrate acidified to pH 1 with concentrated HC1, the precipitate filtered, washed with water, and dried under vacuum to yield 1-METHYLPYRAZOLE-5-CARBOXYLIC acid (85 g, 38percent). The filtrate was concentrated in vacuo to 800 ML, extracted with chloroform (15X400 mL), the organic phase dried over anhydrous magnesium sulfate, concentrated in vacuo, and the residue recrystallized from isopropanol to yield 1-METHYLPYRAZOLE-3-CARBOXYLIC acid (74 g) as a white crystalline solid. A suspension of the acid (90 g, 0.71 mol) and DMF (1 drop) in thionyl chloride (250 ML) was stirred at reflux under nitrogen for 2 h. The solvent was evaporated from the reaction mixture, the residue azeotroped with toluene (3X200 mL), diluted into toluene (250 mL), added to a suspension of Pd-C (10 wtpercent, 9.3 g) in toluene (500 ML), and the mixture stirred at reflux for 8 h with a gentle flow of hydrogen gas through the suspension. After cooling to room temperature, the suspension was filtered through celite, washed with toluene, and concentrated in vacuo. The residue was fractionally distilled under vacuum to provide the title compound (50 g, 63percent) as a low melting white solid (bp = 92 °C COMMAT; 8 MMHG).

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; MERCK & CO., INC.; WO2004/58763; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 28466-21-9, name is 1,3,5-Trimethyl-1H-pyrazol-4-amine, molecular formula is C6H11N3, 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. Recommanded Product: 28466-21-9

Step A (1,3,5-trimethyl-pyrazol-4-yl)-isothiocyanate A mixture of 4-amino-1,3,5-trimethylpyrazole (1.32 g, 10.6 mmol) in 50 mL each of CHCl3 and saturated aqueous NaHCO3 was treated dropwise with thiophosgene (0.812 mL, 10.6 mmol) and stirred vigorously for 20 minutes. The layers were separated and the organic phase was washed with brine. After drying (Na2 SO4), the solvent was evaporated in vacuo to provide the title compound (1.8 g, brown oil) suitable for use directly in the next step. NMR (DMSO-d6, 300 MHz): 2.12 (s, 3H, ArCH3), 2.22 (s, 3H, ArCH3), 3.63 (s, 3H, NHCH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28466-21-9, its application will become more common.

Reference:
Patent; American Home Products Corporation; US6011053; (2000); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics