Analyzing the synthesis route of 5334-40-7

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H3N3O4

Thionyl chloride (6.28ml_, 86.07mmol) was added to an ice cooled solution of 4-nitro-1 H- pyrazole-3-carboxylic acid (10.4 g, 66.21 mmol) in methanol (150 ml_). The resulting solution was stirred at RT O/N. The day after MeOH was removed under vacuum; toluene was added and dried again. The solid was suspended in pentane and filtered under vacuum to afford methyl 4-nitro-1 H-pyrazole-3-carboxylate (p128, 1 1 .15 g, y= 98%) as creamy solid. MS (mlz): 171 .9 [MH]+

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Continuously updated synthesis method about C3H5N3O

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1H-pyrazol-3(2H)-one, its application will become more common.

Electric Literature of 28491-52-3,Some common heterocyclic compound, 28491-52-3, name is 5-Amino-1H-pyrazol-3(2H)-one, molecular formula is C3H5N3O, 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.

5-Amino-2,3-dihydro-1 H-pyrazol-3-one is dissolved in aqueous EtOH containing KOH. To this solution is added methyl 3-(3-trifluoromethyl-phenyl)-3-oxopropanoate and the mixture is stirred under reflux for 1 h 30 min. After cooling to rt, water is added and the mixture is acidified by addition of acetic acid to pH~5. The resulting precipitate is collected on a filter, washed with water and diethyl ether, and dried to give the title compound in moderate yield. Mp >;250 0C (decomp.); 1H-NMR (200 MHz, DMSO-d6), delta (ppm) 5.46 (s, 1 H); 6.05 (s, 1 H); 7.75 (t, 4 Hz, 1 H); 7.89 (d, 4 Hz, 2H); 8.07-8.12 (m, 1 H); 10.90 (br s, 1 H) and 12.25 (br s, 1 H). LC-MS m/z 296 (M+1 )

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1H-pyrazol-3(2H)-one, its application will become more common.

Reference:
Patent; MERZ PHARMA GMBH &; CO. KGAA; HENRICH, Markus; BAUER, Angela; KRUeGER, Bjoern; KAUSS, Valerjans; MUeLLER, Sibylle; KUBAS, Holger; ROZHKOVS, Jevgenijs; PISKUNOVA, Irene; WO2010/139483; (2010); A1;,
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Simple exploration of 56984-32-8

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Related Products of 56984-32-8, 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. 56984-32-8 name is Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate, 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.

General procedure: In a microwave reaction vessel was combined 15(300 mg, 1.59 mmol), phenol (300 mg, 3.19 mmol) and Cs2CO3(1.52 g, 4.66 mmol) in DMF. The vessel was sealed and the resulting mixture was heated at 120C by microwave for30 min. Then the reaction mixture was cooled to r.t., quenched with water and extracted with EtOAc three times. The organic layer was collected, washed with brine, dried over MgSO4 and filtered. After the solvent was removed, the crude was purified by flash column chromatography to yield 16a

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Chen, Zhixiang; Ning, Mengmeng; Zou, Qingan; Cao, Hua; Ye, Yangliang; Leng, Ying; Shen, Jianhua; Chemical and Pharmaceutical Bulletin; vol. 64; 4; (2016); p. 326 – 339;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The important role of 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one

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.

Adding a certain compound to certain chemical reactions, such as: 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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 4149-06-8, Application In Synthesis of 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one

A solution of 3-amino-1-phenyl-2-pyrazolin-5-one 1 (0.35 g, 2 mmol), dimedone 2 (0.28 g, 2 mmol), aldehyde 3 (0.28 mg, 2 mmol) and Cell-LA-TEA+/Fe3O4 nanocatalyst (0.03 g, 0.09 mol%) in H2O/EtOH (3:2) was subjected to ultrasonic irradiation (ultrasonic bath, room temperature). The progress of the reaction was controlled by TLC (hexane/ethyl acetate, 2:3). After reaction completion, the nanocatalyst was separated magnetically from the reaction mixture and used for subsequent cycles after washing with ethanol. By cooling the reaction solution, the solid product was collected, separated and recrystallized from methanol to get the pure product.

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; Zahedifar, Mahboobeh; Pouramiri, Behjat; Razavi, Razieh; Research on Chemical Intermediates; vol. 46; 5; (2020); p. 2749 – 2765;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The important role of 288-13-1

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

Reference of 288-13-1, 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. 288-13-1, name is 1H-Pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1-isopropyl-1H-pyrazole : To a solution of pyrazole (50.0 g, 735.3 mmol) in aqueous sodium hydroxide (123.5 g NaOH/200 ml of water), was added isopropyl bromide (180.0 g, 1470.1 mmol) and the mixture was then heated to reflux for 6-7 days. The reaction mixture was cooled and extracted with ethyl acetate (3 x 300 ml). The combined organic layers were dried over MgS046) delta: 7.72 (d, J= 2.3 Hz, 1H), 7.41 (t, 1H), 6.21 (t, 1H), 4.5 (q, 1H), 1.41-1.37 (d, J= 11.1 Hz).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/12254; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Simple exploration of 5932-34-3

The synthetic route of Ethyl 4-bromo-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Synthetic Route of 5932-34-3, 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. 5932-34-3, name is Ethyl 4-bromo-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a microwave vial was added isopropyl alcohol (10 mL), ethyl 4-bromo-1H-pyrazole-3-carboxylate (from ChemBridge) (788 mg, 3.60 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (48.9 muL, 0.327 mmol) and 4-[3-(cyanomethylene)azetidin-1-yl]-2,5-difluoro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]benzamide (from Example 4 step 4, 1.13 g, 3.27 mmol). The reaction mixture was stirred at 80 C. for 2 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was purified with flash chromatography (eluting with 0-35% ethyl acetate in hexanes) to give the desired product as white foam. 1H NMR (500 MHz, DMSO) delta 8.61 (s, 1H), 8.47 (d, J=8.7 Hz, 1H), 7.34 (dd, J=12.5 and 6.3 Hz, 1H), 6.62 (dd, J=11.9 and 7.3 Hz, 1H), 4.76 (dt, J=15.5 and 7.8 Hz, 1H), 4.61 (d, J=9.2 Hz, 2H), 4.39 (d, J=8.0 Hz, 2H), 4.32 (q, J=7.1 Hz, 2H), 3.68 (s, 2H), 1.31 (m, 6H) ppm. LCMS calculated for C21H20BrF5N5O3 (M+H)+: m/z=564.1. Found: 563.8.

The synthetic route of Ethyl 4-bromo-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Zhuo, Jincong; Qian, Ding-Quan; Mei, Song; Cao, Ganfeng; Pan, Yongchun; Li, Qun; Jia, Zhongjiang; US2014/343030; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

New learning discoveries about C4H6BrN3

The synthetic route of 146941-72-2 has been constantly updated, and we look forward to future research findings.

Electric Literature of 146941-72-2,Some common heterocyclic compound, 146941-72-2, name is 4-Bromo-1-methyl-1H-pyrazol-3-amine, molecular formula is C4H6BrN3, 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 3 Preparation of N-(4-Bromo-1-methylpyrazol-3-yl)-7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]-pyrimidine-2-sulfonamide Pyridine (1.08 g, 8.0 mmol) and dimethyl sulfoxide (0.2 g) were added to a solution of 7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonyl chloride (1.0 g, 4.0 mmol) and 3-amino-4-bromo-1-methylpyrazole (0.70 g, 4.0 mmol) in 10 mL of acetonitrile with stirring at ambient temperature and the mixture was allowed to react overnight. The mixture was then concentrated by evaporation under reduced pressure and the residue was taken up in methylene chloride. The resulting solution was extracted with water and dried over magnesium sulfate. The volatile materials were then removed by evaporation under reduced pressure and the solid residue was extracted with diethyl ether and with water, recovered by filtration, and dried under reduced pressure to obtain 0.38 g (25 percent of theory) of the title compound as a white solid melting at 230-232 C. Elemental Analysis: Calc. for C10 H12 BrClN7 O3 S:%C, 28.2; %H, 2.84; %N, 23.0 Found: %C, 28.0: %H, 2.42; %N, 23.2 1 H NMR Spectrum: (delta ppm from TMS) 10.9 (bs, 1H), 7.84 (s, 1H), 7.83 (s, 1H), 4.23 (s, 3H), and 3.66 (s, 3H).

The synthetic route of 146941-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DowElanco; US5201938; (1993); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Analyzing the synthesis route of 5-Phenyl-1H-pyrazole-3-carboxylic acid

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

Adding a certain compound to certain chemical reactions, such as: 5071-61-4, name is 5-Phenyl-1H-pyrazole-3-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 5071-61-4, Product Details of 5071-61-4

To a solution containing 0.31 g (1.65 mmol) of 5-phenyl-1H-pyrazole-3-carboxylic acid and 3 mL of DMF was added 0.77 g (1.82 mmol) of COMU, 0.28 g (1.73 mmol) of tert-butyl(3-aminopropyl)carbamate, and 0.45 mL (2.5 mmol) of DIPEA. The reaction mixture was allowed to stir at rt overnight, quenched by the addition of 10% HCl in water, and extracted with DCM. The combined organic layers were dried by passage through a phase separator cartridge and the solvent was removed under reduced pressure. The residue was subjected to silica gel chromatography to give 0.59 g (100%) of tert-butyl (3-(5-phenyl-1H-pyrazole-3-carboxamido)propyl)carbamate as a yellow oily solid. LC/MS ret. time=1.124 min, m/z=289.30 [M-C(CH3)3]+.

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

Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Waterson, Alex G.; Beauchamp, R. Daniel; (77 pag.)US2016/52896; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Extracurricular laboratory: Synthetic route of 4-Pyrazol-1-yl-phenylamine

Statistics shows that 4-Pyrazol-1-yl-phenylamine is playing an increasingly important role. we look forward to future research findings about 17635-45-9.

Synthetic Route of 17635-45-9, These common heterocyclic compound, 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine, 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 11 4-Pyridinecarboxyaldehyde 4-(pyrazol-1-yl)phenylhydrazone; [Show Image] 4-(Pyrazol-1-yl)phenylamine (646 mg) was dissolved in water (10 ml) and concentrated hydrochloric acid (10 ml), and an aqueous solution (4 ml) of sodium nitrite (336 mg) was added to the solution at 0°C over 30 minutes. After stirring at the same temperature for 30 minutes, a concentrated hydrochloric acid solution (3 ml) of tin chloride dihydrate (1.83 g) was added to the mixture, followed by stirring at room temperature for 30 minutes. The reaction mixture was alkalified by adding 20percent aqueous solution of potassium hydroxide and extracted with chloroform: methanol = 9:1 (100 ml) twice. After drying over anhydrous sodium sulfate, the solvent was evaporated to obtain a reddish brown residue. The residue and 4-pyridinecarboxyaldehyde (324 mul) were dissolved in ethanol (8 ml) and heated under reflux for 15 hours. The solvent was evaporated, and then the residue was purified by flash silica gel column chromatography (chloroform: methanol = 10:1) to obtain the title compound (107 mg) as a reddish brown solid. 1H-NMR (400 MHz, D2O) delta: 6.35 (1H, s), 6.95 (2H, d, J=8.6 Hz), 7.14 (1H, s), 7.22 (2H, d, J=9.0 Hz), 7.47 (2H, d, J=5.8 Hz), 7.51 (1H, s), 7.76 (1H, s), 8.07 (2H, d, J=5.8 Hz). ESI-MS m/z: 264 (M+H)+

Statistics shows that 4-Pyrazol-1-yl-phenylamine is playing an increasingly important role. we look forward to future research findings about 17635-45-9.

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

Brief introduction of 37599-58-9

The synthetic route of 37599-58-9 has been constantly updated, and we look forward to future research findings.

Electric Literature of 37599-58-9, These common heterocyclic compound, 37599-58-9, name is (1H-Pyrazol-3-yl)methanamine, 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 5 mL microwave reaction vial equipped with a stirbar was charged with 4-fluoro-2- hydroxy-5-(N-(4-isopropoxyphenyl)sulfamoyl)benzamide (Example 107, 0.250 gl) and (1 H-pyrazol-3-yl)methanamine (0.198 g). The solids were taken up in 1 -butanol (3.4 mL) and the resulting reaction mixture was subjected to microwave irradiation at 1 10 C with stirring on high absorption setting for 2 sessions of 2 h each for a total of 4 h reaction time. The reaction mixture was resubjected to microwave irradiation at 140 C with stirring for an additional 2 sessions of 2 h and 8 h (14 h total microwave reaction time). The mixture was then cooled to room temperature, diluted with ethanol to ~20 mL total volume, filtered, and concentrated to a residue. The residue was taken up in a minimum amount of DMSO for purification by reverse phase silica gel using a 30 gram RediSep Gold C18 reverse phase silica cartridge (0-90% acetonitrile in 0.2M aq ammonium acetate). Fractions containing the desired material were pooled and then concentrated to remove the acetonitrile. The aqueous layer was acidified to ~pH 4.5 by addition of 1 N aq hydrochloric acid. The mixture was extracted twice with ethyl acetate and the organic layers were pooled, dried over sodium sulfate, filtered, and concentrated to dryness. The solid mass was triturated with diethyl ether to afford the title compound as an off-white solid (52 mg. LCMS m/z 446.3 (M+H)+. 1H NMR (400 MHz, DMSO-c/6) delta ppm 1 .13 – 1 .23 (m, 6 H) 4.38 (d, J=5.58 Hz, 2 H) 4.47 (spt, J=6.04 Hz, 1 H) 6.13 (s, 1 H) 6.16 (d, J=2.03 Hz, 1 H) 6.63 – 6.81 (m, 3 H) 6.89 – 7.01 (m, 2 H) 7.62 (br. s., 2 H) 8.06 (s, 1 H) 8.27 (br. s., 1 H) 9.81 (br. s., 1 H) 12.52 (br. s., 1 H) 13.74 (br. s., 1 H).

The synthetic route of 37599-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics