pyrazoles-derivatives

Synthetic Route of 3273-44-7, These common heterocyclic compound, 3273-44-7, name is 5-Methyl-1H-pyrazole-3-carbaldehyde, 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: To a suspension of 5-methyl-1H-pyrazole-3-carbaldehyde (18; 2-6 equiv) in anhydrous THF (10 mL) (in the case of the synthesis of 1) or MeOH (in the case of the synthesis of 2-5 and 11), the corresponding derivative bearing one to three amino groups (17,21 25-289d,11 or 36,4c see Scheme 1 and Scheme 2) (1 equiv), dissolved in anhydrous MeOH (5 mL), was added. The resulting mixture was heated at reflux until a clear solution resulted and then stirred at r.t. (up to 4 days, TLC analysis). The resulting imines were reduced without further purification by addition of NaBH4 (3-9 equiv) in portions. After complete addition of the reducing agent, the reaction mixture was stirred for 24 h at r.t. and then the solvent was removed under reduced pressure. The residue was suspended in CHCl3-H2O (1:1, 10 mL) and stirred for 12 h at r.t. The resulting suspension was extracted with CHCl3 (3 × 20 mL), dried over MgSO4, and the solvent was removed. The crude product was purified by column chromatography.

Statistics shows that 5-Methyl-1H-pyrazole-3-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 3273-44-7.

Reference:
Article; Koch, Niklas; Seichter, Wilhelm; Mazik, Monika; Synthesis; vol. 48; 17; (2016); p. 2757 – 2767;,
Pyrazole – Wikipedia,
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51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, 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. HPLC of Formula: C10H7ClN4

General procedure: Equimolar portionsof the intermediate compounds 1 (1 mmol) and the intermediatecompounds 3 (1 mmol) were dissolved in approximately 8 mL ofethanol. The reaction solution was allowed to stir at 80 8C for 2 huntil the reaction was complete. The reaction was monitored byTLC. Mostly, a precipitate formed and was then collected by suctionfiltration.

The synthetic route of 51516-67-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Li, Dong-Dong; Ruan, Ban-Feng; Li, Qing-Shan; Chu, Ming-Jie; Ai, Cheng-Ying; Liu, Dao-Hong; Mo, Kai; Cao, Hai-Qun; Chinese Chemical Letters; vol. 28; 2; (2017); p. 377 – 382;,
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Some common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, molecular formula is C8H14N4O, 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. category: pyrazoles-derivatives

General procedure: To a solution of aromatic aldehydes 8 (1.0 mmol) in acetonitrile, 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 10 (1.0 mmol) and InCl3 (10 mol%) were added at room temparature and the reaction mixture was stirred till the completion of the starting materials (indicated by TLC). The solvent was evoparated and the crude product was triturated with 10% diethyl ether in hexane to obtain the pure product. The product was identified by 1H NMR, 13 C NMR and Mass.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 139756-02-8, its application will become more common.

Reference:
Article; Mulakayala, Naveen; Kandagatla, Bhaskar; Ismail; Rapolu, Rajesh Kumar; Rao, Pallavi; Mulakayala, Chaitanya; Kumar, Chitta Suresh; Iqbal, Javed; Oruganti, Srinivas; Bioorganic and Medicinal Chemistry Letters; vol. 22; 15; (2012); p. 5063 – 5066;,
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Related Products of 3398-16-1, A common heterocyclic compound, 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, molecular formula is C5H7BrN2, 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: Ethyl 5-(chloromethyl)furan-2-carboxylate (5a, 2.0 g, 10.60 mmol) was added to a solution of 3,5-dimethyl-1H-pyrazole (6a) (1.019 g, 10.60 mmol), KOtBu (1.547 g, 13.79 mmol) and TBAI (0.392 g, 1.060 mmol) in THF (53 ml) at 0 °C. The mixture was allowed to warm up to rt and was stirred at rt for 24 h. To the reaction mixture was added satd NH4Cl aq, and then the mixture was extracted with EtOAc. The organic layers were combined, washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel column chromatography (hexane/EtOAc), which yielded the pyrazole 7a (1.25 g, 47.5percent) as a brown oil. Pyrazoles 7b?e were synthesized in a similar way.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yasuda, Yorinobu; Arakawa, Takeaki; Nawata, Yumi; Shimada, Sayaka; Oishi, Shinya; Fujii, Nobutaka; Nishimura, Shinichi; Hattori, Akira; Kakeya, Hideaki; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1776 – 1787;,
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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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1H-Pyrazole-4-carbaldehyde

To a stirred solution of pyrazole carboxaldehyde (2-1, 300 mg, 3.1 mmol) in tetrahydrofuran was sequentially added 3,4-dihydro-2H-pyran (2-2, 867 mg, 10.3 mmol) and catalytic amount of trifluoroacetic acid. The resulting solution was refluxed for 4 h and then cooled to rt. The reaction was quenched by addition of trace amount of sodium hydride. Solvent was removed under vacuum and the residue was purified by silica gel chromatography to give 2-3 (520 mg, 92percent). MS (ESI+): m/z: 181.1 (M+H)+.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANGION BIOMEDICA CORP.; LI, An-Hu; DANA, Dibyendu; LIM, Dong Sung; GADHIYA, Satishkumar; JUNG, Dawoon; NARAYAN, Prakash; ALI, Quaisar; PAKA, Latha; GOLDBERG, Itzhak D.; (93 pag.)WO2019/46795; (2019); A1;,
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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. 41680-34-6, name is 3-Amino-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 41680-34-6

A solution of 5-amino-1H-pyrazole-4-carboxylic acid (2000 mg, 15.74 mmol) and (E)-3- (dimethylamino)-2-methylacrylaldehyde (1780 mg, 15.74 mmol) in acetic acid (3 mL) and ethanol (1 mL) was heated at 70 oC for 1h. The resulting mixture was cooled to room temperature and the solid was collected by filtration, washed with water and dried in vacuum to afford 6-methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid (1610 mg, 58%) as a white solid. MS (ESI): m/z = 178.1 [M+1]+.

The synthetic route of 41680-34-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
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Reference of 78703-53-4, A common heterocyclic compound, 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H8N2O2, 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 solution of ethyl acetoacetate (40 mmol) and triethyl orthoformate (60 mmol) in acetic anhydride (0.12 mol) was refluxed for 8 hours. After completion of the reaction, the product was distilled under reduced pressure to give crude product (1).Then, the intermediate (1) (40 mmol) was added dropwise to a mixture of methylhydrazine (60 mmol) and ethanol (20 mL) and reacted at 60 C for 8 hours. After completion of the reaction, the residue was distilled under reduced pressure, (20 mL) was extracted with saturated brine, and the organic layer was partitioned with anhydrous sodium sulfate and evaporated to give 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylate (2) The pyrazole ester 2 was stirred at room temperature for 12 hours in a solution of sodium hydroxide in ethanol. After removing the solvent ethanol, the solid was dissolved in water, hydrochloric acid was added, and a white solid 3 was precipitated.A solution of 14 g (0.1 mol) of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid (3) was charged into a 250 mL single-necked flask, 75 mL of SOCl2 was added slowly, heated under reflux for 4 h, and the reaction was complete by TLC. SOCl2 to give a pale yellow solid. 2.5 mmol of thiocyanate was dissolved in 15 ml of anhydrous acetonitrile, and then two drops of PEG-200 were added to the mixture, followed by stirring at room temperature for 5 min.Subsequently, 1 mmol of the acetonitrile solution of the compound 4 was added, and the mixture was stirred at room temperature for 40 minutes. The mixture was filtered to obtain an acetonitrile solution of pyrazolecarbonyl isothiocyanate and then substituted aniline (0.85 mmol) was added.After stirring at room temperature for 3-4 hours, the reaction mixture was evaporated in vacuo and the residue was subjected to silica gel column chromatography using petroleum ether and ethyl acetate as the solvent to give the product.

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; Zhejiang University of Technology; Liu Xinghai; Wang Han; Zhai Zhiwen; Shen Zhonghua; Tan Chengxia; Weng Jianquan; Wu Hongke; Sun Nabo; (10 pag.)CN107033082; (2017); A;,
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 360056-45-7 as follows. COA of Formula: C5H7N3O2

Step 1. Synthesis of 4-(2,6-difluoro-benzoylaminoVlH-pyrazole-3-carboxylic acid ethyl ester; A mixture of 2,6-difluorobenzoic acid (6.32 g, 40.0 mmol), 4-amino-lH-pyrazole- 3-carboxylic acid methyl ester (5.68 g, 40.0 mmol), EDC (8.83 g, 46.1 mmol) and HOBt (6.23 g, 46.1 mmol) in DMF (100 ml) was stirred at ambient temperature overnight. The mixture was reduced in vacuo, the residue taken up in ethyl acetate and then washed with saturated aqueous sodium hydrogen carbonate, water and brine. The organic extracts was dried (MgSO4) and reduced in vacuo to give 4- (2,6-difluoro-benzoylamino)-lH-pyrazole-3-carboxylic acid methyl ester as a yellow solid (9.94 g). (LC/MS: Rt 2.81, [M+H]+ 282.01).

According to the analysis of related databases, 360056-45-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; NOVARTIS AG; WO2008/7123; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 2075-46-9, A common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

Dissolving 5.0 g of 4-nitropyrazole in 160 mL of ethanol, and then adding 0.8 g of 10 wt% Pd/C to the above solution; Hydrogen was introduced into the reaction solution and allowed to react overnight at room temperature; after the TLC detection reaction was completed, the insoluble matter was filtered off with diatomaceous earth; Evaporation of the ethanol solvent gave pure intermediate 2 as a red solid 3.6 g.

The synthetic route of 2075-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Zhang Yingjie; Liang Xuewu; Xu Wenfang; (47 pag.)CN108864057; (2018); A;,
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Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 81945-73-5, name is 1H-Pyrazol-1-ol, molecular formula is C3H4N2O, 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 1H-Pyrazol-1-ol

EXAMPLE 1 part of 1-hydroxypyrazole is mixed thoroughly with 4 parts of potassium carbonate, and the mixture is introduced into an autoclave. Carbon dioxide is forced in at room temperature until the pressure reaches 50 bar, after which heating is carried out for 20 hours at 150 C. The reactor content is then dissolved in water, the solution is acidified with hydrochloric acid, which precipitates the 1-hydroxypyrazole-4-carboxylic acid, and the latter is filtered off and recrystallized from water. 0.68 part (45% of theory) of 1-hydroxypyrazole-4-carboxylic acid of melting point 230 C. is obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 81945-73-5, its application will become more common.

Reference:
Patent; BASF Aktiengesellschaft; US4769473; (1988); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics