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. 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile

General procedure: An equimolar mixture of Int-I (chalcones) and Int-II (5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile) was refluxed in n-butanol for 4-5 h. The completion of reaction was confirmed by Thin Layer Chromatography using (6:4- hexane: ethyl acetate) as a mobile phase. The reaction mixture was then allowed to cool and the resulting solid was filtered and washed with diethyl ether to remove impurities. The procedure was repeated 3-4 times to free the product from impurities.

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; Baluja, Shipra; Nandha, Kajal; Journal of Molecular Liquids; vol. 201; (2015); p. 90 – 95;,
Pyrazole – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 2075-45-8, name is 4-Bromo-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 2075-45-8, category: pyrazoles-derivatives

A 100 mL round bottom flask was charged with 4-bromopyrazole (4.41 g, 30 mmol), tetrabutylammonium bromide [(484] mg, 1.5 mmol) and potassium hydroxide pellets (3.37 g, 60 mmol). After the mixture was sonicated for 15 min, benzyl chloride (5.2 [ML,] 45 mmol) was added dropwise and the resulting mixture was stirred overnight. Ethyl ether (20 mL), water (20 mL), and diluted hydrochloric acid (1 [ML,] [10%)] were added under stirring. The organic layer was washed with water [(2X20] mL) and dried over MgS04. The solvent was removed under reduced pressure and the product was purified by flash chromatography on silica gel (hexane/ethyl acetate 10: 1) to provide the desired product as a white solid (6.74 g, 95% yield). Mp [51-52 C] (lit. [44-45 C,] See Jones, R. G. [J.] Am. [CHEM.] Soc. 1949, [71,] [3994).’H NMR] (400 MHz, CDC13) : [8] 7.53 (s, 1H), 7.42-7. 33 (m, 4H), 7.28-7. 22 (m, 2H), 5.29 (s, 2H); [13C] NMR (100 MHz, CDC13) : [6] 140.4, 136.2, 129. 8, 129.4, 128.8, [128.] 3,93. 9, 57.1.

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

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2004/13094; (2004); 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. 943541-20-6, name is 3-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 943541-20-6

Quinazolin-6-yl-acetic acid hydrazide (0.032 g, 0.158 mmol) and 3-chloro-6-(l- methyl-lH-pyrazol-4-yl)-pyridazine (0.031 g, 0.158 mmol) were heated to 165C in 5 butanol (2 mL) for five hours. The reaction was cooled to room temperature, evaporated in vacuo and purified via silica gel column chromatography eluting with 5% methanol in dichloromethane to give 0.0031g (7%) of 6-[6-( 1 -methyl- IH- pyrazol^-yO-tl^^triazolo^.S-blpyridazin-S-ylmethyll-quinazoline. 1H NMR (400 MHz, CD3OD) 5 8.45 (s, IH), 8.29 (s, IH), 8.06 (d, 2H, J=9.6Hz), 7.60 (d, 2H, J=9.6Hz), 7.55 (m, IH), 7.17 (d, IH, J==8.0Hz), 6.08 (s, IH), 4.58 (m, 2H), 3.89 (s, 3H). Mass spectrum (LCMS, ESI pos.): Calcd for Ci8H)4N8; found: 343.3 (M+H).

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 943541-20-6.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/75567; (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. 21230-43-3, name is Ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 21230-43-3

(1) Synthesis of ethyl 3-chloro-1-methylpyrazole-4-carboxylate: Into a solution of 150 ml of conc. HCl, 50 ml of phosphoric acid (85%), 41.4 g of ethyl 3-amino-1-methylpyrazole-4-carboxylate and 100 ml of water, there was added dropwise a 50 ml of aqueous solution of 18.6 g of sodium nitrite at 0 C. or lower. The reaction mixture was added dropwise into a solution of 90 g of cupric sulfate (pentahydrate) and 60 g of sodium chloride dissolved in 200 ml of water at room temperature. The mixture was heated for an hour at 50 C. and after cooling, followed by extraction with chloroform. After washing with water and drying, evaporation of the solvent gave 44.8 g of ethyl 3-chloro-1-methylpyrazole-4-carboxylate. m.p.: 65-66 C.

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; Nissan Chemical Industries, Ltd.; US4668277; (1987); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 852227-86-2, 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. 852227-86-2, name is 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

10171] Step 4. A mixture ofD-15 (210 mg, 0.78 mmol) and cesium carbonate (765 mg, 2.35 mmol) in DMF (25 mL) was heated to 60 C. with stirring then a solution of 5-(chlorom- ethyl)-1,3-dimethyl-1H-pyrazole (113 mg, 0.78 mmol) in DMF (10 mL) was added drop wise. The reaction mixture was stirred for 1 hour at 60 C. The solids were removed by filtration and the solvent was removed under reduced pressure. Crude D-16 was used as such in the next step.10172] LC-MS: Anal. Calcd. For C18H28N503: 376.22; found 377 [M+H]

The chemical industry reduces the impact on the environment during synthesis 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; McGowan, David; Raboisson, Pierr Jeane-Marie Bernar; Embrechts, Werner; Jonckers, Tim Hugo Maria; Last, Stefaan Julien; Pieters, Serge Maria Aloysius; Vlach, Jaromir; US2014/45849; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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. name: 4-Nitro-1H-pyrazole

4-Nitro-1H-pyrazole 12 (10.0 g, 88.4 mmol) was taken in CH3CN (100 mL) in a 250 mL round bottom flask under N2. To it were sequentially added iodomethane (18.8 g, 132.0 mmol) and K2C03 (30.5 g, 221.0 mmol). The reaction mixture was heated at 100C for 1 6h. The reaction mixture was then poured into ice water (100 g) and extracted with EtOAc (3 x 100 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was further washed with n-pentane to afford 15 as a light yellow solid (10.8 g, 96% yield). ?H NMR (400 MHz, CDC13): 88.11 (s, 1H), 8.05 (s, 1H), 3.96 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2075-46-9, its application will become more common.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Application of 113100-53-1, A common heterocyclic compound, 113100-53-1, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, molecular formula is C6H5F3N2O2, 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: Intermediate 5 (1.0 mmol) and 4-dimethylaminopyridine (0.1 mmol) were added to a mixture of the corresponding carboxylic acid 6 (1.3 mmol) and (EDCI, 2 mmol) in CH2Cl2 (20 mL). The reaction system was stirred at room temperature overnight and then diluted with CH2Cl2 (50 mL). The resulting mixture was consecutively washed with 10% citric acid solution and brine. Then the organic phase was dried with sodium sulphate and filtered, and concentrated under reduced pressure. The residue was purified on a silica gel column to afford the title compounds 7-17.

The synthetic route of 113100-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xiong, Li; Zhu, Xiao-Lei; Shen, Yan-Qing; Kandergama Wasala Mudiyanselage Wishwajith, Wickramabahu; Li, Kui; Yang, Guang-Fu; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 424 – 434;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 108161-12-2, A common heterocyclic compound, 108161-12-2, name is 3,5-Dimethyl-1H-pyrazole-4-carbonitrile, molecular formula is C6H7N3, 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.

4,6-dichloropyrimidine (1.27 g, 8.50 mmol), 3,5-dimethyl-1H-pyrazole-4-carbonitrile (1.03 g, 8.50 mmol) and caesium carbonate were dissolved in DMF. The reaction mixture was stirred at room temperature overnight. Water was added and the resulting mixture was stirred at room temperature for 30 min. The precipitate was filtered, washed with water and dried under reduced pressure to afford the desired product 1.06 g (53 % yield), which was used as such in the next step. LC-MS (method 11): Rt = 1.28 min; MS (ESIpos): m/z = 234 [M+H]+1H-NMR (400 MHz, DMSO-d6) delta [ppm] : 2.339 (0.76), 2.378 (15.68), 2.403 (1.58), 2.732 (0.44), 2.781 (0.70), 2.826 (16.00), 2.868 (1.38), 2.891 (0.55), 5.754 (0.68), 8.014 (2.62), 9.038 (2.54).

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 AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; KLAR, Juergen; EHRMANN, Alexander; WILLWACHER, Jens; ENGEL, David; DIESKAU, Andre Philippe; KAHNERT, Antje; GROMOV, Alexey; SCHMECK, Carsten; LINDNER, Niels; MUeLLER, Thomas; ANDREEVSKI, Anna Lena; DREHER, Jan; COLLINS, Karl; (861 pag.)WO2018/69222; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 25016-11-9, 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 25016-11-9 as follows.

To a solution of l-methyl-IH-pyrazole-4-carbaldehyde (104a)(4.8 g, 43.6 mmol) in tetrahydrofuran (80 mL) was cooled to 0 C was added dropwise (3- (bis(trimethylsilyl)amino)phenyl)rnagnesium chloride (49c) (49.0 mL, 49.0 mmol) and stirred at 0 C for 2 h. The reaction was quenched with saturated aqueous NH4CI (1 20 mL)and extracted with ethyl acetate (2 x 120 rnL). The combined organic extracts were washed with brine (100 mL), dried over MgSO4 followed by filtration and concentration. The residue was dissolved in ether (200 mL), treated with 4 N HCI in I ,4-dioxane (24 mL) and stirred at room temperature for 2 h. The solid obtained was collected by filtration washedwith ether, dried under vacuum to give (3-aminophenyl)(l-methyl-IH-pyrazol-4- yl)methanol (104b) (6.01 g, 68%) as an off-white solid; ?H NMR (300 MHz, DMSO-d(,) 8 7.47 (s, 111), 7.46- 7.20 (in, 5H), 5.69 (s, I H), 3.76 (s, 3H); MS (ES+) 204.1 (M+1).

According to the analysis of related databases, 25016-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; WU, Minwan; CHINTAREDDY, Venkat, R.; KUMAR, V., Satish; ZHANG, Weihe; WO2015/134998; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 50877-42-4, name is 1-Benzyl-4-iodo-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 50877-42-4, Safety of 1-Benzyl-4-iodo-1H-pyrazole

General procedure: To a solution of 4-iodo-1-methyl-1H-pyrazole (3.0 g, 14.4 mmol, 1.0 eq.), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (835 mg, 1.4 mmol, 0.1 eq.) and palladium(II) acetate (415 mg, 0.7 mmol, 0.05 eq.) in dioxane (72.1 ml, 0.2 M) was added N,N’-diisopropylethylamine (5.0 mL, 28.9 mmol, 2.0 eq.) and benzylmercaptan (2.0 ml, 17.3 mmol, 1.2 eq.). The reaction mixture was stirred at 100 C for 18 h. The reaction mixture was diluted with ethyl acetate (300 mL) and water (150 mL). The aqueous layer was extracted with ethyl acetate (150 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography.

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-Benzyl-4-iodo-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vernier, William F.; Gomez, Laurent; Tetrahedron Letters; vol. 58; 49; (2017); p. 4587 – 4590;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics