Category: pyrazoles-derivatives

Application of 31037-02-2,Some common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H11N3O2, 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.

The acid chloride reaction solution was synthesized in the same manner as in Example 1.75 g of water, 67 g of pyrazole amine, 42 g of sodium carbonate and 5 g of triethylamine were added to 1000 ml, cooled to 0 to 5 C, and acyl chlorideThe reaction solution was controlled at a temperature of 5 to 10 C. The dropwise addition was completed and the reaction was completed for 1 hour. The reaction was completed, the layers were separated and the organic phase was dissolved to obtain a crude product.Add 200g of methanol heated to 50 C dissolved, cooled to 5 C, precipitated the solid, filtered to give the product as a white solid, yield:82%, content: 95%.

The synthetic route of 31037-02-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Fuding Chemical Co., Ltd.; Liu, Dongwei; Cheng, Lizhong; Chang, Qing; Dong, Hailong; Zhu, Ruiyu; Gu, Junkun; (11 pag.)CN106631896; (2017); A;,
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Related Products of 10250-64-3,Some common heterocyclic compound, 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, molecular formula is C11H10N2O2, 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 solution of 19 (1.2 eq) and HOBt(1.4 eq) in DMF (0.5 M) were added EDCI (1.3 eq) and a solution of 15a-j or 16a-j (1.0 eq) in DMF (0.25 M), Et3N (3.5 eq) at 0 C. The reaction mixture was stirred at room temperature for 24 hours, then diluted in AcOEt. The organic phase was washed with water twice, saturated aqueous NaHCO3 three times, and brine, then dried over Na2SO4,filtered, and concentrated. The residue was purified by flash column chromatography to give intermediates 17a-j and 18a-j.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, its application will become more common.

Reference:
Article; Nakagawa, Hidehiko; Seike, Suguru; Sugimoto, Masatoshi; Ieda, Naoya; Kawaguchi, Mitsuyasu; Suzuki, Takayoshi; Miyata, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 25; 23; (2015); p. 5619 – 5624;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1260243-04-6,Some common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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 mixture of ethyl 5-amino-1H-pyrazole-4-carboxylate obtained in the step 1) (15.5 g, 0.01 mol) and 1-p-fluorophenyl-4,4,4 , -trifluorobutanedione (23.4 g, 0.1 mol) was placed in a vessel; 3.2) Dissolve the mixture in a container with 50 ml of glacial acetic acid to give a mixture E, placing the container on an electric heating barHeating to 115 ° C;3.3) The mixture E was heated to reflux for 7 hours, cooled, allowed to stand, and precipitated as a yellow-green needle-like solid;Ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [l, 5-a] pyrimidine-3-carboxylate was obtained after filtration, washing and drying;The process used in the process is cold glacial acetic acid.The mass of the product ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [l, 5_a] pyrimidine-3-carboxylate obtained in 27.05 g. Yield: 76.63percent.

The synthetic route of 1260243-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chongqing Medical College; Shi, Lei; Niu, Ya Hui; (7 pag.)(2016);,
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. 60061-68-9, name is 4-Bromo-3-methyl-5-(trifluoromethyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-3-methyl-5-(trifluoromethyl)-1H-pyrazole

Synthesis of 1-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-2-(4-bromo-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone Protocol T was followed using 4-Bromo-5-methyl-3-trifluoromethyl-1H-pyrazole, K2CO3, 2-Chloro-1-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethanone and DMF. Column chromatography using a solvent mixture (hexane/ethyl acetate=2/3) afforded the title compound as white solid. 1H NMR (400 MHz, CDCl3) delta 6.96-7 (m, 2H), 6.84-6.9 (m, 2H), 5 (s, 2H), 3.6-3.8 (m, 4H), 3.02-3.16 (m, 4H), 2.3 (s, 3H). 13C NMR (400 MHz, CDCl3) delta 162.6, 146.5, 142, 118.5, 116, 52.2, 50.4, 46, 42.2, 15.

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; ChemoCentryx, Inc.; US2004/162282; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-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. Recommanded Product: 578008-32-9

Intermediate 90(S)-4-(3-((tert-Butyldimethylsilyloxy)methyl)morpholino)-6-(l-(3,5-difluoropyridin-2-vD-2- methoxyethoxy)-5-fluoro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-2-amine (3,S<)-3-({[fert-Butyl(dimethyl)silyl]oxy}methyl)-4-{2-chloro-6-[l-(3,5-difluoropyridin-2-yl)-2- methoxyethoxy]-5-fluoropyrimidin-4-yl}morpholine (Intermediate 62), tert-butyl 3-amino-5- methyl-lH-pyrazole-1-carboxylate (Intermediate 10), BINAP, Pd2(dba)3, and CS2CO3 in dioxane (2 ml) was heated at 950C for 8h. LCMS indicated complete reaction. Methanol (1 ml) was added and the reaction was stirred at r.t for Ih. Solvent was removed under reduced pressure and the reaction mixture was purified by ISCO column. The material obtained was directly used in the subsequent step without further purification. LCMS: 610[M+eta]+. The synthetic route of tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate has been constantly updated, and we look forward to future research findings. Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/132502; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 120068-79-3, 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. 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Comparative Example 13; [0123] Direct sulfinylation of N-phenyl pyrazole starting material (III) according to known methods was tested. As such, sulfinylation was attempted using CF3SO2Na in the presence of a halogenating agent such as POCl3, SOCl2 or PBr3. (III) (II)The reaction reagents and conditions tested are provided in Table I below. Table IUl The results are provided in Table II below: Table II[0124] The reaction proceeded to the desired product, Fipronil, when SOCl2 or POCl3 were used as halogenating agents. However, PBr3 did not yield the desired product, or at least not in acceptable yield (about 6%~8% (II) in the reaction mixture, according to HPLC).

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, 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VETOQUINOL; WO2009/77853; (2009); 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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Amino-1H-pyrazole-4-carbonitrile

To a solution of 3-amino-4-cyanopyrazole (100 g, 0.9 mol) in DMF (1 L) is added NBS (197.5 g, 1.1 mol) and mixture is stirred for 10 h at ambient temperature. The mixture is concentrated in vacuo then dissolved in EtOAc and washed with brine (8×). The organics are collected and concentrated in vacuo to afford I-70 (50 g, 29%) m/z 187.0 [M+].

The synthetic route of 16617-46-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BENTZIEN, Joerg Martin; BERRY, Angela Kay; BOSANAC, Todd; BURKE, Michael Jason; DISALVO, Darren Todd; HORAN, Joshua Courtney; LIANG, Shuang; MAO, Can; MAO, Wang; SHEN, Yue; SOLEYMANZADEH, Fariba; ZINDELL, Renee M.; US2014/45813; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 16078-71-0, These common heterocyclic compound, 16078-71-0, name is Ethyl 5-amino-1-phenyl-1H-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.

Ethyl 5-amino-1-phenylpyrazole-4-carboxylate (2.31 g) was added to 20 mL of formamide and heated to 180 C. for 4 hours.Cool to room temperature, add 30ml of water, filter and filter cake washed with ethanol (2 x 10mL).Obtained 1-phenyl-pyrazole [3,4-d]pyrimidine-4-one, 1.93 g, 91% yield, HPLC: 98.08%.

Statistics shows that Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate is playing an increasingly important role. we look forward to future research findings about 16078-71-0.

Reference:
Patent; Central South University of Forestry and Technology; Ma Qiang; Wang Wenlei; Hu Yunchu; Xie Lianwu; Wen Ruizhi; (8 pag.)CN107955008; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 18048-64-1, 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 18048-64-1 as follows.

5- (2-hydroxy-3-amino-5,6,7,8-tetrahydronaphthalen-2-yl) – furan-2-carboxylic acid(1.0g, 3.66m mol), dissolved in 40ml 1mol / l of HCl solution, cooled to0 , thereto was slowly added dropwise of NaNO2(303 mg of the, 4.39m mol) in 40ml aqueoussolution; BI dropwise, maintaining the reaction temperature of the reaction was continued for 30min, TLC trace starting material 5- (2-hydroxy – 3-amino-5,6,7,8-tetrahydronaphthalen-2-yl) -furan-2-carboxylic acid.Was added1- (3,4-dimethylphenyl) methyl-1H-pyrrol-5 (4 hydrogen) -one (740 mg of, -3-3.66m mol), adjusted pH with saturated sodium bicarbonate solution after 15min about 8, was added40ml of absolute ethanol, the reaction naturally to room temperature.24h after LC-MS testing of raw materials reactionwas complete.Filtered, the filter cake washed with water to prepare a suspension adjust PH around 5, and then filtered, the filter cake after dryingcolumn chromatography to obtain the target product (Z) -5- (3- (2- (1- (3,4-dimethyl phenyl) -3-methyl-5-oxo-1,5-dihydro – pyrazol-4-ylidene) hydrazino) -2-hydroxy-5,6,7,8-tetrahydronaphthalene -1 -yl) – furan-2-carboxylic acid (compound 18) (192mg, 10.8% yield).

According to the analysis of related databases, 18048-64-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Qilu Pharmaceutical Co., Ltd; Wang, Jingyi; Fan, Chuanwen; Zhang, Long; Yan, Shousheng; Zhang, Soming; Zhao, Hongbing; Zhou, Haojie; Yang, Chuanwei; Zhao, Hongling; Yang, Yingying; (46 pag.)CN103360317; (2016); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37718-11-9, name is 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 37718-11-9, Formula: C4H4N2O2

In a 3L three-necked bottle, 1H-pyrazole-4-carboxylic acid (SM1, 112.0 g, 1.0 mol) and DMF (500 ml) were added and controlled.The system temperature is 0-5°C, and a solution of 254 g (2.0 mol) oxalyl chloride in DMF (500 ml) is slowly added dropwise to the solution of oxalyl chloride in DMF.During the liquid process, the temperature of the control system is maintained at 0-5°C. After the DMF solution of the acyl chloride reagent is added dropwise,Warm to room temperature (25-30°C) and stir for 2h. Then spin to obtain 1H-pyrazole-4-carboxylic acid chloride;

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Pyrazole-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Xiamen Hailejing Biochemical Co., Ltd.; Qiu Binglin; Chen Huadong; Zhong Baoxiang; Li Jinlin; Huang Zhizheng; (14 pag.)CN107915738; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics