Day: August 13, 2021

Synthetic Route of 3463-30-7, These common heterocyclic compound, 3463-30-7, name is 1-(4-Nitrophenyl)-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.

Reference Example 13 4-(Pyrazol-1-yl)phenylamine Under hydrogen atmosphere, an ethanol solution (80 ml) of 1-(4-nitrophenyl)pyrazole (2.91 g) and 5percent palladium-carbon (1.4 g) was stirred at room temperature for 24 hours. After filtration of the catalyst, the filtrate was concentrated under reduced pressure and then purified by flash silica gel column chromatography (hexane:ethyl acetate = 1:1) to obtain the title compound (2.45 g) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 3.73 (2H, br s), 6.41 (1H, br s), 6.75 (2H, d, J=8.5 Hz), 7.44 (2H, d, J=8.5 Hz), 7.67 (1H, s), 7.78 (1H, s).

The synthetic route of 3463-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1612204; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1280210-79-8, A common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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.

Under N2 protection and a condition free of water and oxygen, Intermediate 2 (604 mg, 2.87 mmol) wasdissolved in tetrahydrofuran (20 ml), which was cooled to 0C, and sodium hydride (180 mg, 60 wt%, 4.5 mmol) wasadded, followed by stirring for 30 min. Cyclopropylsulfonyl chloride (1.27 g, 9.0 mmol) was added dropwise, and thetemperature was allowed to rise spontaneously to room temperature, followed by reaction for 1 hour. The reaction was quenched by addition of water (20 ml) to the reaction solution, which was then extracted with ethyl acetate (20 ml32).The organic phases were combined, dried over anhydrous sodium sulfate, concentrated, re-dissolved in 5 ml tetrahydrofuran,and cooled to -10C to 0C. Potassium t-butoxide (36 mg, 0.32 mmol) was added, and the reaction was allowedto proceed for 28 hours at this temperature. After the reaction was completed, an aqueous solution of citric acid (1 ml,15%) was added, and water (10 ml) was added. The solution was extracted with ethyl acetate (20 mL33). The organicphases were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gelcolumn chromatography (petroleum ether/ethyl acetate (v/v) = 2:1) to obtain a white solid 1a (660 mg, yield 73%).

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); 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. 400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate

Step 3 Preparation of 4-amino-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester A mixture of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid methyl ester (500 mg, 2.7 mmol) and 10% palladium on carbon (50 mg) in methanol (25 mL) was subjected to 60 psi pressure of hydrogen gas in a Parr apparatus for 24 h. At this time, the reaction mixture was filtered through a pad of celite and washed with methanol. The filtrate was concentrated in vacuo to afford 4-amino-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester (402 mg, 96%) as an off-white solid: 1H NMR (DMSO-d6, 300 MHz) delta7.10 (s, 1H), 4.65 (broad s, 2H), 3.73 (s, 3H), 3.72 (s, 3H).

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; Dunten, Peter W.; Foley, Louise H.; Huby, Nicholas J.S.; Pietranico-Cole, Sherrie L.; Yun, Weiya; US2004/14766; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route 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: The corresponding pyrazole derivative 18, 19 or 22 (4 or 7 equiv) was dissolved in alkaline DMF [containing NaOH (4 or 7 equiv)] and the solution was stirred for 30 min at r.t. The bromomethyl-substituted benzene derivative 21 or 23 (1 equiv) was added and the reaction mixture was stirred for 24?48 h at 70 °C. The solution was cooled to r.t., then poured into ice water (50 mL), and the resulting precipitate was collected by filtration, washed thoroughly with H2O (3 × 15 mL) and dried in a desiccator.

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

Reference:
Article; Koch, Niklas; Mazik, Monika; Synthesis; vol. 45; 24; (2013); p. 3341 – 3348;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3112-31-0, A common heterocyclic compound, 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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.

To a 25 mL reactor, 174.0 mg of 3,5-pyrazoledicarboxylic acid monohydrate and 250.0 mg of copper sulfate pentahydrate powder were added, 5 mL of 4-methylpyridine and 10 mL of water were added, and after stirring for 15 minutes, the reaction kettle was placed in an oven. Heating to 180 ° C, the reaction is 24 hours;After the reaction is completed, the reaction solution is transferred to a flask, and 2 mL of a saturated aqueous solution of sodium sulfide is added to the reaction solution, and after the precipitation is completed, it is filtered;adding 1M hydrochloric acid solution to the filtrate droplet obtained in the second step, adjusting the solution pH=3, and filtering;The fourth step: extracting the filtrate obtained in the third step (3×20 mL) using an organic solvent dichloromethane, collecting the organic phase, and drying with anhydrous sodium sulfate for 10 h;the organic phase obtained after the fourth step of drying was concentrated and dried to obtain 71.0 mg of a white powder, which was designated as sample 3.

The synthetic route of 3112-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Fujian Structure Of Matter Institute; Huang Deguang; Xiang Shiqun; Zhang Xiaofeng; (13 pag.)CN109369617; (2019); A;,
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. 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Methyl-4-nitro-1H-pyrazole

A mixture of a portion (0.7 g) of the material so obtained, platinum oxide (0.05 g), ethyl acetate (5 ml) and ethanol (15 ml) was stirred under 3 atmospheres pressure of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. There was thus obtained the required starting material (0.6 g); 1H NMR: (DMSOd6) 3.64 (s, 3H), 6.86 (s, IH), 6.97 (s, IH).

The synthetic route of 3994-50-1 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

4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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. Recommanded Product: 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one

General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

The synthetic route of 4149-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 96799-02-9, These common heterocyclic compound, 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, 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.

Example 21 To a solution of cyanuric chloride (230 mg, 1.25 mmol) in THF (16 mL) was added (S)- l-(4-fluorophenyl)ethylamine (0.16 mL, 1.25 mmol) and DIPEA (0. 20 mL, 1.25 mmol) at 0 C. The reaction mixture was let to stir at 0 C to room temperature for 2h. 3-amino- 5-(2-furyl)pyrazole (187 mg, 1.25 mmol) and DIPEA (0.20 mL, 1.25 mmol) were added to the above mixture and the resulting mixture was heated with microwave initiator at 150 C for 10 minutes. 1-methylpiperazine (0.28 mL, 2.50 mmol) and DIPEA (0.44 mL, 2.50 mmol) were added to the mixture and the mixture was heated with microwave initiator at 60 C for 10 minutes. Saturated NaHCO3 in water was added and the mixture was extracted by ethyl acetate (3 x 50 mL). The combined organic was washed by brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a silica gel column eluted with 0-5 % MeOH/DCM afforded 21 as light brown solid (52 mg, 9 %). 1H NMR (400 MHz, DMSO-d6,80C) delta 12.46 (bs, 1H, NH), 9.52 (bs, 1Eta, NH), 8.55 (bs, 1Eta, NH), 7.63-6.04 (m, 8Eta, Ar-H), 5.12 (bs, 1Eta, CH), 3.67 (bs, 4Eta, 2CH2), 2.30 (bs, 4Eta, 2CH2), 2.21 (s, 3Eta, CH3), 1.47 (s, 3Eta, CH3), 1.45 (s, 3Eta, CH3); ESI-MS: calcd for (C23Eta26FN9O) 463, found 464 [M+H]+. HPLC: retention time: 17.10 min. purity: 99%.

The synthetic route of 96799-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; HO, David; NALLAN, Laxman; POLAT, Tulay; SUN, Xiaowen; DESAI, Neil; WO2010/144394; (2010); A1;,
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 25016-12-0 as follows. Recommanded Product: 25016-12-0

General procedure: Aldehyde (1.0 equiv) is a dissolved in anhydrous methanol (0.2-0.5 mM) and charged with cesium carbonate (1.0 equiv) and cooled to 0-5 oC . Dimethyl (1-diazo-2-oxopropyl)phosphonate (1.0 equiv) is added dropwise after which the reaction is allowed to stir for 1-18h after which the crude mixture is concentrated onto silica gel and purified directly by flash silica gel chromatography to provide the desired alkyne J-1.

According to the analysis of related databases, 25016-12-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo, C.; EVANS, Catherine, A.; TREMBLAY, Martin, R.; (288 pag.)WO2016/54491; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 294877-29-5, name is 1-(3-Bromophenyl)-3,5-dimethyl-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 294877-29-5, HPLC of Formula: C11H11BrN2

In another step, 2-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-N-(tetrahydropyranyl)carbazole was synthesized. To a 100 mL sealed tube was added with N-tetrahydropyranyl-2-hydroxycarbazole (880 mg, 3.0 mmol), N-(3-Bromophenyl)-3,5-dimethylpyrazole (826 mg, 3.30 mmol), Cesium carbonate (2.9 g, 3 mmol), copper(I) iodide (57 mg, 0.3 mmol), N,N-dimethylglycine (93 mg, 0.9 mmol) and 1,4-dioxane (8 mL) in glove box, and the mixture was stirred at 90 C. for 3 days. After cooling to rt, the mixture was treated with water (75 mL) and ethyl acetate (40 mL), and the water phase was extracted with ethyl acetate (3×30 mL). The organic extracted phase was combined, washed with brine (3×30 mL), dried with magnesium sulfate and concentrated. The resulting crude product was purified with an silica gel chromatography with hexane/ethyl acetate=3:1 as eluent to give an white colloidal solid. (1.12 g, 79% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Bromophenyl)-3,5-dimethyl-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; Li, Jian; Turner, Eric; Hang, Xiaochun; US2012/215001; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics