Day: September 27, 2021

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., Formula: C5H4BrF3N2

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

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.

Example 122: Preparation of l-difluoromethyl-3-trifluoromethyl-l//-pyrazole-4- carboxylic acid ethyl ester and 2-difluoromethyl-3-trifluoromethyl-2/:/-pyrazole-4- carboxylic acid ethyl esterSodium hydride (60% in mineral oil) (320 mg, 7.93 mmol) was washed with hexane (2x 10 ml) and suspended in tetrahydrofiiran (20 ml) in a three necked flask. 3- Trifluoromethyl-l//-pyrazole-4-carboxylic acid ethyl ester (1.5 g, 7.21 mmol) (prepared according to JP 2000/044541) in tetrahydrofiiran (10 ml) was added dropwise and the solution stirred at room temperature for 30 minutes. Chlorodifluoromethane was bubbled through the solution for 5 minutes and then the mixture was stirred at room temperature for 3 hours, with additional chlorodifluoromethane bubbled through the solution after every hour for 5 minutes. The reaction mixture was stored at room temperature for 16 hours. The reaction mixture was quenched by addition of water and extracted with ethyl acetate. The organic extract was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: 0-25% ethyl acetate in hexane) to give l-difluoromethyl-3-trifluoromethyl- l//-pyrazole-4-carboxylic acid (isomer A) (870 mg, 47% yield) and 2-difluoromethyl-3- trifluoromethyl-2H-pyrazole-4-carboxylic a’cid (isomer B) (500 mg, 27% yield). Isomer A 1H-NMR (400 MHz, CDCl3): 1.37 (t, 3H, Me), 4.37 (q, 2H, CH2), 7.37 (t, IH, CH), S.07 (s, IH, CH) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 1.37 (t, 3H, Me), 4.37 (q, 2H, CH2), 7.22 (t, IH, CH), 8.43 (s, IH, CH) ppm.

Statistics shows that Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate is playing an increasingly important role. we look forward to future research findings about 155377-19-8.

Reference:
Patent; SYNGENTA LIMITED; WO2007/71900; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference 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

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

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. Product Details of 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

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. 948570-75-0, name is 1-(2-Methoxyethyl)-4-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

1-(2-methoxyethyl)-4-nitro-1H-pyrazole (84 mg, 0.49 mmol) and -chloro-6-(2,6-dichloro-3,5-dimethoxy phenyl)pyrido[3,4-d]pyrimidine (200 mg, 0.54 mmol) were dissolved into DMA (15 mL), then CuI (112 mg, 0.59 mmol), PivOH (15 mg, 0.15 mmol), K2CO3 (88 mg, 0.64 mmol) and Pd(PPh3)2Cl2 (34 mg, 0.05 mmol) were added, the mixture was heated to 140 C. under N2 and stirred for 1 h. The reaction was completed, and the mixture was concentrated to remove the sol vent by reduced pressure and separated by fast silica gel column (PE/EA 2:1) to obtain compound 6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-(1-(2-methoxyethyl)-4-nitro-1H-pyrazol-5-yl)pyrido[3,4-d]pyrimidine (103 mg, yield 42%). MS m/z (ESI): 505 [M+1]+.

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; Abbisko Therapeutics Co., Ltd.; YANG, Fei; DENG, Haibing; YING, Haiyan; YU, Hongping; CHEN, Zhui; XU, Yaochang; (604 pag.)US2019/270742; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 294877-29-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 294877-29-5 name is 1-(3-Bromophenyl)-3,5-dimethyl-1H-pyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Synthesis of 3-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9,9-dimethyl-10-(pyridin-2-yl)-9,10-dihydroacridine ON’1 ligand To a solution of Fg-1 (302 mg, 1 mmol) in DMSO (5 mL) were added 1-(3-bromophenyl)-3,5-dimethyl-1H-pyrazole (301 mg, 1.2 mmol), CuI (19 mg, 0.1 mmol), 2-picolinic acid (25 mg, 0.2 mmol), and K3PO4 (318 mg, 1.5 mmol) under the protection of N2. The mixture was heated to 100 C. and maintained at this temperature for 2 days. The reaction was cooled to room temperature and 20 mL was then added. The mixture was extracted with ethyl acetate and dried with anhydrous Na2SO4.

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; Arizona Board of Regents on behalf of Arizona State University; Li, Jian; Li, Guijie; Zhu, Zhi-Qiang; US2015/349279; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 35277-02-2, 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. 35277-02-2, name is 4-Fluoro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Synthesis of 5-(4-fluoro-lH-pyrazol-l-yl)pyrazine-2-carbonitrile. (0362) To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-lH-pyrazole (170 mg, 2.0 mmol) and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at 100 C for 4 hours, then cooled to 20 C, poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and purified by column chromatography (hexane: ethyl acetate = 5: 1) to give 5-(4-fluoro-lH- pyrazol-l-yl)pyrazine-2-carbonitrile (310 mg, 82%). The structure was confirmed by LC-MS.

The synthetic route of 4-Fluoro-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; KIM, Joseph, L.; WILSON, Kevin, J.; WILSON, Douglas; DIPIETRO, Lucian, V.; (84 pag.)WO2017/79140; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, 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 72760-85-1, Product Details of 72760-85-1

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.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Baluja, Shipra; Nandha, Kajal; Journal of Molecular Liquids; vol. 201; (2015); p. 90 – 95;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine, 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 17635-45-9, Quality Control of 4-Pyrazol-1-yl-phenylamine

General procedure: A dry 50 mL capacity carousel reaction tube was charged with the relevant substituted indole (1.5 mmol), and this starting material dissolved in dry THF (12 mL). Oxalyl chloride (144 muL, 209 mg, 1.65 mmol) was added and the mixture stirred at room temp. After 24 h, either N,N-diisopropylethylamine (590 muL, 438 mg, 3.4 mmol) or 2,6-lutidine(396 muL, 364 mg, 3.4 mmol) was introduced to the reaction, followed by the relevant amine (1.8 mmol). The temperature was raised to 45 °C, and heating continued for 18 h. The solvent was evaporated, then the residue resuspended in a mixture of ethyl acetate (20 mL) and brine (10 mL) and stirred vigorously for 30 min. After passing through a liquid-liquid extraction column, ensuring washing through of the column with additional ethyl acetate, a second extraction was carried out with sat. NH4Cl (10 mL) in the same manner. Product solutions were then evaporated to dryness giving the crude indole-3-glyoxylamide derivatives, which were purified as necessary (see Supplementary Information for individual compound details). Typically, two sequential recrystallizations, from ethyl acetate-hexane followed by 2-propanol-water, afforded final products of good purity. For products derived from poorly nucleophilic anilines (p-1H-pyrazol-1-ylaniline,p-pyrrol-1-ylaniline and p-morpholinoaniline), a further modification was used. Immediately following introduction of the arylamine to the reaction mixture, DMAP (18 mg, 0.15 mmol, 10 molpercent) was added to assist the final step, as its use was found to enhance the extent of conversion in the final step in such cases.

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-Pyrazol-1-yl-phenylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Thompson, Mark J.; Louth, Jennifer C.; Ferrara, Steven; Jackson, Matthew P.; Sorrell, Fiona J.; Cochrane, Edward J.; Gever, Joel; Baxendale, Sarah; Silber, B. Michael; Roehl, Henry H.; Chen, Beining; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4125 – 4132;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics