Month: May 2021

Synthetic Route of 20154-03-4, 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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1?3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5?10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C?N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

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

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 14531-55-6, name is 3,5-Dimethyl-4-nitro-1H-pyrazole, molecular formula is C5H7N3O2, 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. Computed Properties of C5H7N3O2

6.72 g (47.6 mmol) 3,5-Dimethyl-4-nitro-1H-pyrazole were heated with 7.52 g (57.1 mmol) 3-(chloromethyl)-5-methyl-1,2-oxazole (CAS-No. 35166-37-1) and 8.53 mL (57.1 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene in 25 mL dimethylsulfoxide to 60C overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried, filtered, and evaporated. The crude title compound (10 g) was used without further purification. 1H NMR (400 MHz, DMSO-d6): delta [ppm] = 2.37 (s, 3H), 2.39 (s, 3H), 2.61 (s, 3H), 5.42 (s, 2H), 6.16 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14531-55-6, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; BUCHMANN, Bernd; CLEVE, Arwed; SIEBENEICHER, Holger; KOPPITZ, Marcus; SCHNEIDER, Dirk; BAUSER, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (482 pag.)WO2016/202898; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

General prodedure: NaH (1 mmol) was suspended in DMF (8 mL), then 3-amino-1-phenyl-2-pyrazolin-5-one (1) (0.48 mmol) was dissolved in DMF (10 mL) and added slowly. The mixture was stirred for 30 min at 0 C. Next vinamidinium salt 2 (0.48 mmol) was added and the resulting mixture heated at 80 C for 6 h and the residue partitioned between CH2Cl2 and H2O. The aqueous layer was extracted with CH2Cl2 and the combined organic layers dried over Na2SO4, filtered and the solvents removed in vacuo. The crude residue was purified by column chromatography (10% EtOAc in hexane) to give products 3a-e. For pyrazolo[3,4-b]pyridine 3f, after evaporation of the solvent, THF (6 mL) and 1 N HCl (6 mL) were added. The mixture was allowed to stir at room temperature for 2 h, then neutralized with saturated aqueous NaHCO3 and extracted with CH2Cl2 (3 × 15 mL). Work-up and purification as above gave 3f.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Samar, Chtiba; Fayel, Jemmezi; Jameleddine, Khiari; Tetrahedron Letters; vol. 52; 28; (2011); p. 3648 – 3650;,
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. name: 3-Methyl-4-nitro-1H-pyrazole

In analogy to example 6-2, 98.2 mg (0.46 mmol) of a mixture of 4-[(4-amino-3- methyl-1H-pyrazol-1-yl)methyl]benzonitrile and 4-[(4-amino-5-methyl-1H-pyrazol-1- yl)methyl]benzonitrile (intermediate 17C-2 and 18C-2) and 102 mg (0.39 mmol) 6- methyl-2-phenylquinoline-4-carboxylic acid ([CAS-No. 60538-98-9], commercially available at e.g. Enamine, Chemical Diversity Labs, Matrix, Zerenex), were reacted to give after purification using a Biotage chromatography system (25 g snap KP-Sil column, hexane / 50- 100% ethyl acetate, then ethyl acetate / 0- 100% methanol) followed by a separation and purification via preparative HPLC (method 6a) 121 mg (67% yield) of the desired example 41 and 16 mg (9.0% yield) of the desired example 42-2. N-[1-(4-cyanobenzyl)-3-methyl-1H-pyrazol-4-yl]-6-methyl-2-phenylquinoline-4- carboxamide, example 41-2: 1H-NMR (400 MHz, DMSO d6) delta (ppm) = 2.21 (s, 3H), 2.52 (s, 3H), 5.41 (s, 2H), 7.44 (d, 2H), 7.49 – 7.61 (m, 3H), 7.68 (dd, 1H), 7.85 (d, 2H), 7.90 (s, 1H), 8.06 (d, 1H), 8.23 (s, 1H), 8.30 – 8.34 (m, 3H), 8.36 (s, 1H), 10.34 (s, 1H). N-[1-(4-cyanobenzyl)-5-methyl-1H-pyrazol-4-yl]-6-methyl-2-phenylquinoline-4- carboxamide, example 42-2: 1H-NMR (400 MHz, DMSO d6) delta (ppm) = 2.24 (s, 3H), 2.53 (s, 3H), 5.47 (s, 2H), 7.32 (d, 2H), 7.50 – 7.62 (m, 3H), 7.69 (dd, 1H), 7.84 – 7.88 (m, 2H), 7.89 (s, 1H), 7.96 (s, 1H), 8.06 (d, 1H), 8.26 (s, 1H), 8.31 – 8.36 (m, 2H), 10.27 (s, 1H).

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; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; BUCHMANN, Bernd; CLEVE, Arwed; SIEBENEICHER, Holger; KOPPITZ, Marcus; SCHNEIDER, Dirk; BAUSER, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (482 pag.)WO2016/202898; (2016); A1;,
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. 89179-62-4, name is 1-Methyl-1H-pyrazole-3-carboxamide belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 89179-62-4

To a solution of 1-methyl-1H-pyrazole-3-carboxamide (400 mg, 3.2 mmol) in dioxane (30mL) was added LAH (365 mg, 9.6 mmol). The resulting mixture was stirred for 3 h at 100°C.After it was cooled to 0°C, it was quenched with 0.4 ml water, 0.4 mL 15percent NaOH aqueous, 1.2mL water in tum. Anhydrous sodium sulfate was added to the solution. The mixture was filteredand concentrated to give the crude product which was used for the next step directly.

The synthetic route of 89179-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; MCCOMAS, Casey C.; REGER, Thomas S.; QI, Changhe; WO2014/139150; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 20154-03-4,Some common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, molecular formula is C4H3F3N2, 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 3-trifluoromethyl-1H-pyrazole (500 mg, 3.67 mmol) in glacial acetic acid (5 ml) was added a 10percent solution of sodium hypochlorite in water (2188 mul, 3.67 mmol). The reaction mixture was stirred at RT overnight and then neutralized with sat. sodium carbonate, and extracted with DCM. The organic layers were combined washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give the desired product (480 mg, 77percent) as a white solid which did not require further purification. MS (ISP) 169.0 (M-H)-.

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

Reference:
Patent; Conte, Aurelia; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2007/185058; (2007); 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., category: pyrazoles-derivatives

3-Methyl-1H-pyrazole (0.66 g, 8 mmol) and potassium tertbutoxide (0.88 g, 7.8 mmol) were dissolved in dry dimethyl sulfoxide (DMSO) (5 mL) at room temperature. To the basic solution, 2-bromopyridine (1.17 g, 7.4 mmol) was added slowly under constant stirring, and the solution was heated to reflux under nitrogen for 12 h. Once the reaction completed, it was cooled to room temperature and extracted with water and ether. The organic layer was washed withwater and ether to remove DMSO and excess base. The organic layer was then isolated, dried over anhydrous Na2SO4, and filtered. The solvent was then removed under reduced pressure, and the resultant colorless oil was purified by column chromatography on silica gel (200e300 mesh) eluted with hexane/ethylacetate (9:1 v/v). 1H NMR (500 MHz, CD2Cl2) delta (ppm): 8.43 (1H, d, J 2.53), 8.38 (1H, d, J 4.88), 7.91 (1H, d, J 8.30), 7.79e7.74 (1H, m), 7.59-7.47 (1H, m), 6.25 (1H, d, J 2.53), 2.38 (3H, s).

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; Sunesh, Chozhidakath Damodharan; Subeesh, Madayanad Suresh; Shanmugasundaram, Kanagaraj; Chitumalla, Ramesh Kumar; Jang, Joonkyung; Choe, Youngson; Dyes and Pigments; vol. 128; (2016); p. 190 – 200;,
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 25016-20-0 as follows. Quality Control of 1-Methyl-1H-pyrazole-3-carboxylic acid

Compound 1007; (2R.6S, 12Z, 13aS, 14aR, 16aS)-2-{[7-methoxy-8-methyl-2-(propan-2-yloxy)quinolin-4- yl]oxy}-N-[(1-methylcyclopropyl)sulfonyl]-6-{[(1 -methyl- 1 H-pyrazol-3- yl)carbonyl]amino}-5,16-dioxo-1, 2,3,6,7,8,9,10,11,13a,14,15,16,16a- tetradecahydrocyclopropa[e]pyrrolo[1 ,2-a][1 ,4]diazacyclopentadecine-14a(5H)-Ca; Acid R2a (6.6 mg, 0.052 mmol, 1.3 equiv) is dissolved in DMF (0.5 ml_), then TEA (28muIota_, 0.20 mmol, 5.0 equiv) is added followed by TBTU (15.4 mg, 0.048 mmol, 1.2 equiv). The solution is stirred for 15 mins, after which the amine hydrochloride Ca is added in DMF (0.5 mL) and this solution is stirred at RT for 16 h. Water (2 mL) is added to the solution, and then the organic layer is extracted with EtOAc (3×5 mL) and dried over MgS04. The solvent is evaporated and the residue is purified on prep HPLC (MeCN:H20, 0.1% TFA). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1007.FIA M.S.(electrospray) : 820.3 (M+H)+ Retention time (min): 5.7 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1H) , 8.93 (s, 1H), 7.83 (d, 1H, J = 8.8 Hz), 7.79 (d, 1H, J= 7 Hz), 7.77 (d, 1H, J = 2.1 Hz), 7.08 (d, 1H, J = 9 Hz), 6.60 (d, 1H, J = 2.3 Hz), 6.37 (s, 1H), 5.66-5.58 (m, 1H), 5.62 (S, 1H, J = 6.2 Hz), 5.47-5.44 (m, 1H), 5.07 (dd, 1H, J = 9.5, 9.2 Hz), 4.64-4.54 (m, 1H) 4.52 (d, 1H, J = 11.6 Hz), 4.40 (dd, 1H, J = 9.7, 7.1 Hz), 4.02 (dd, 1H, J = 11.8, 3.5 Hz), 3.89 (s, 3H), 3.88 (s, 3H), 2.66-2.57 (m, 1 H) , 2.51 (s, 3H), 2.43 (s, 3H), 2.38-2.29 (m, 2H), 2.02-1.90 (m, 1H), 1.88-1.77 (m, 1H), 1.58 (dd, 1H, J =8.2, 5.1 Hz), 1.52 (dd, 1H, J =9.3, 5.2 Hz), 1.45-1.35 (m, 12H), 1.34-1.20 (m, 4H), 0.93-0.84 (m, 2H).

According to the analysis of related databases, 25016-20-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 288-13-1, These common heterocyclic compound, 288-13-1, name is 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.

4-Nitropyrazole is available commercially from the N.D. Zelinsky Institute, Organic Chemistry, Leninsky prospect 47, 117913 Moscow B-334, Russia. The compound may also be prepared as follows :- s Fuming nitric acid (9.5 ml) was added dropwise to a stirred solution of pyrazole(13.6 g) in glacial acetic acid (51 ml) that had been cooled to -100C using an ice-salt bath. A voluminous precipitate was formed. Acetic anhydride (27 ml) was added dropwise and the resultant mixture was stirred at ambient temperature for 2.5 hours. The mixture was poured onto ice and the acidity of the mixture was reduced to pH5 by the addition of potassium 0 carbonate. The precipitate was isolated by filtration. The resultant solid was dissolved in water and the aqueous solution was extracted with diethyl ether. The organic solution was dried over magnesium sulphate and filtered. Petroleum ether (b.p. 60-80°C, 50 ml) was added to the filtrate which was concentrated by evaporation to a volume of about 50 ml. A precipitate formed which was isolated by filtration. This solid was believed to be S 1-nitropyrazole (20.6 g); 1H NMR: (DMSOd6) 6.71 (s, IH), 7.88 (s, IH), 8.81 (s, IH). The compound may be explosive and should be handled cautiously.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/99326; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, 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 176969-34-9, HPLC of Formula: C6H6F2N2O2

General procedure: Under nitrogen atmosphere, carboxylic acid II (3mmol), EDCI (3.3 mmol), HOBT (3.3 mmol)and Et3N (1.8 mmol) were placed in a three-necked flask with 40 mL CH2Cl2, and stirred for 2 hat 0 C; then, compound I (2.4 mmol) was added to the flask and allowed to react for 3 h at 0 C.The reaction was monitored by thin-layer chromatography (TLC) (all reactions could be completed in3 h) and, on completion of the reaction, the mixture was washed with saturated NaHCO3 solutionand water, respectively. Then, it was dried over anhydrous Na2SO4, filtered and evaporated onrotavapor in vacuum. Subsequently, crude products III-1-III-18 were purified by silica gel columnchromatography [V (CH2Cl2): V (EA) = 3:1] and crude products III-19-III-36 were purified by silicagel column chromatography [V (PE): V (EA) = 3:1]. Finally, products were recrystallized with thedichloromethane/petroleum ether to obtain pure target compounds.

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-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Shen; Meng, Siqi; Xie, Yong; Yang, Yonggui; Zhang, Yumeng; He, Lu; Wang, Kai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Li, Xinghai; Molecules; vol. 24; 14; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics