Category: pyrazoles-derivatives

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 118430-73-2 as follows. Formula: C8H15N3

Example I; Synthesis Example I (Preparation of Exemplified compound (1)); [Show Image] A mixture of 41.4 g of 4-nitroaniline (0.3 mol), 84 ml of conc. hydrochloric acid, 60 ml of acetic acid and 84 ml of propionic acid was stirred at an inner temperature ranging from 0 C to 5C. To the mixture was dropped 20.7 g (0.3 mol) of sodium nitrite per 45 ml of water at an inner temperature of 5 C or less. Thereafter, stirring was continued for 30 minutes at an inner temperature ranging from 0 C to 5 C. The resultant diazonium salt solution was dropped to 600 ml of acetonitrile solution containing 46.0 g (0.3 mol) of 5-tert-butyl-2-methyl-2H-pyrazole-3-ylamine at an inner temperature of 10 C or less. After the dropwise addition of the diazonium salt solution, the resultant reaction solution was kept stirring for 2 hours, followed by injection of 1000 ml of water. Then, the precipitated azo dye was separated by a filtration. Recrystallization of the produced crystals was performed with 1650 ml of methanol, to obtain Exemplified compound (1). Yield: 72 g (80%), Melting point: 199 C to 201 C. lambdamax (ethyl acetate solution) of Exemplified compound (1) was 444 nm.

According to the analysis of related databases, 118430-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; EP1903078; (2008); A2;,
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. 309740-49-6, name is Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate

General procedure: To a solution of intermediate 488 (2.26 g, 9.45 mmol) in dry DCM (25.4 mL) was added dropwise diisobutylaluminium hydride (3.62 mL, 20.31 mmol) at – 50 C. The reaction mixture was stirred at – 50 C for 3 h then at rt for 2 h. The mixture was acidified at 0 C with a 3N aqueous solution of HCl and diluted with Et20. The organic layer was separated, washed with a IN aqueous solution of HCl, then twice with brine, dried over MgS04 and evaporated in vacuo. The residue (2.17 g) was purified by column chromatography on silica gel (irregular SiOH, 40 muiotaeta, 40 g, mobile phase: heptane/EtOAc, gradient from 100:0 to 60:40). The pure fractions were combined and the solvent was evaporated to give 536 mg of intermediate 489 (27% yield).

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; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 151049-87-5, These common heterocyclic compound, 151049-87-5, name is 3-Bromo-1-methyl-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.

To a solution of (5-(methoxycarbonyl)thiophen-3-yl)boronic acid (5.30 g, 28.5 mmol) and 3-bromo-i-methyl-iH-pyrazole (4.59 g, 28.5 mmol) in dioxane (108 mL) were added Pd(PPh3)4 (1.04 g, 1.42 mmol) and 1.5 M aqueous K3PO4solution (57 mL, 85 mmol). The resulting mixture was heated at 80 C for ih, then cooled, diluted with CH2C12, dried over Na2504, filtered through a pad of silic, and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexanes, to give the title compound. MS: m/z = 223 (M + 1). ?H NMR (400 MHz, CDC13) oe 8.18 (s, iH), 7.80(s, iH), 7.40(s, iH), 6.44(s, iH), 3.96(s, 3H), 3.94 (s, 3H).

Statistics shows that 3-Bromo-1-methyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 151049-87-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STUMP, Craig A.; CHEN, Yi Heng; LIU, Ping; MENG, Dongfang; WU, Jane; LI, Chun Sing; QI, Zhiqi; (163 pag.)WO2016/161572; (2016); 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. 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 141573-95-7

In a 100 mL reaction flask, add ethyl 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate(38 mmol) represented by formula (II), and then add 10% by mass 30mL NaOH aqueous solution, heated to 60 C and stirred until the reaction solution was transparent, and then naturally cooled to room temperature. The reaction solution was adjusted to pH about 2.0 by adding acid, a large amount of solid was precipitated, filtered by suction, and the filter residue was washed with water and dried to obtain the formula 1) -methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid.

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; Cai Pengpeng; Jin Tao; Tan Chengxia; Weng Jianquan; Wu Hongke; (11 pag.)CN110669007; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 4149-06-8, These common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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 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.

Statistics shows that 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one is playing an increasingly important role. we look forward to future research findings about 4149-06-8.

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

Electric Literature of 155377-19-8, These common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, 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 11 Ethyl 3-trifluoromethylpyrazole-4-carboxylate (5 g), potassium carbonate (3.48 g) and ethyl iodide (2.3 ml) in acetonitrile were heated at reflux overnight. After cooling, ethyl acetate and water were added and the organic phase separated. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried (magnesium sulphate) and evaporated under reduced pressure to give a yellow oil which was purified by crystallisation in hexane to produce 4-ethoxycarbonyl-1-ethyl-3-trifluoromethylpyrazole as white crystals (3.65 g), 1 H NMR (CDCl3) delta1.25(3H,t), 1.45(3H,t), 4.10(2H,q), 4.20(2H,q) 7.90(1H,s) ppm.

The synthetic route of 155377-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Agriculture Limited; US5480857; (1996); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2458-26-6, name is 3-Phenyl-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 2458-26-6, Safety of 3-Phenyl-1H-pyrazole

Examples 42-48Preparation of N-(2,6-difluorophenyl)[5-(1-methyl-3-phenylpyrazol-5-yl](2-thienyl)}carboxamide (93) To a solution of 90 (1 g, 6.9 mmol) in THF (50 mL) was added NaH (0.66 g, 27.6 mmol). The mixture was stirred for 1 h and the MeI (1.97 g, 13.8 mmol) was added in one potion. The reaction mixture was stirred for 18 h at room temperature. The reaction was quenched with MeOH and solvent was removed in vacuo. The residue was treated with water and EtOAc. The organic layer was separated and aqueous was extracted with EtOAc. The combined organic phase was dried over Na2SO4, filtered, concentrated to give crude product. The crude product was purified on ISCO columns. Fractions containing pure product were combined and evaporated. The yellow oil 91 (0.53 g, 48%) was obtained.

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

Reference:
Patent; CalciMedica, Inc.; US2012/53210; (2012); 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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Amino-1,3-dimethylpyrazole

To a solution of 5-amino-1,3-dimethylpyrazole (300 mg, 2.70 mmol) in dichloromethane (3 mL) was added at ambient temperature under a nitrogen atmosphere N-BOC-(4′-chlorophenyl)glycine (771 mg, 2.70 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (569 mg, 2.97 mmol), 1-hydroxybenzotriazole (36 mg, 0.27 mmol) and N,N-diisopropyl ethyl amine (693 mul, 4.05 mmol). The resulting reaction mixture was was stirred for 18 h at this temperature. The solution was diluted with ethyl acetate (20 mL) and washed with aqueous sodium carbonate (half saturated, 20 mL), water (20 mL) and brine (20 mL). The combined aqueous layers were extracted with ethyl acetate (20 mL) and the combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 0:100) afforded the title compound (656 mg, 64%) as a colorless oil. MS m/e: 379.3 [M+H]+.

The synthetic route of 3524-32-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark; US2009/312314; (2009); A1;,
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. 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

General procedure: Diisopropyl azodicarboxylate (DIAD, 1.5 equiv) was added dropwise to a stirred solution of alcohol 1a-g (1-2 equiv), N,N?-bis-tert-butoxycarbonylpyrazole-1H-carboxamidine 2 (2.5 mmol, 1 equiv), and Ph3P (1.5 equiv) in THF (7 mL) at 0 C. The reaction mixture was stirred overnight (16 h) at r.t., concentrated in vacuum, and the residue was purified by flash column chromatography on silica gel (10-25% EtOAc-hexane) to give the N-alkylated guanylating agent 3a-g as colorless oils.

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 152120-54-2.

Reference:
Article; Tommasi, Sara; Zanato, Chiara; Carabeo, Rey; Mangoni, Arduino A.; Dall’Angelo, Sergio; Zanda, Matteo; Synthesis; vol. 47; 19; (2015); p. 3067 – 3078;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 82560-12-1, A common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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 microwave vial was charged with 3-tert butyl- lH-pyrazole-5 -amine (1.03 g, 7.39 mmol), copper (I) iodide (70.3 mg, 0.37 mmol) and potassium carbonate (2.14 g, 15.5 mmol) and the vial sealed with a septum, evacuated and purged with argon. Trans- N,N’-dimethylcyclohexane-l,2-diamine (210 mg, 1.48 mmol) was then added, then a solution of Intermediate Vc (4.26 g, 8.86 mmol) in toluene (7.5 mL, degassed with argon) was added, and the reaction was subjected to microwave irradiation (150 C for 1 h). The reaction mixture was then filtered through Celite, and the filtrate concentrated in vacuo. Purification by FCC, eluting with 0 – 60% EtOAc/cyclohexane, to afford the title compound (2.41 g, 66%). LCMS (Method 3) Rt 4.68 min, m/z 493, 495 [MH+].

The synthetic route of 82560-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; HURLEY, Christopher; CRIDLAND, Andrew, Peter; JENNINGS, Andrew, Stephen, Robert; WO2014/195402; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics