Tag: M.W:100-200

Electric Literature of 89088-55-1, 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. 89088-55-1, name is 5-Bromo-1-methyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of compound 11-3 (2.0 g, 5.4 mmol) and K2C03 (2.2 g, 16.2 mmol) in dioxane (40 mL) and H20 (4 mL) were added 5-bromo-l-methyl-lH-pyrazol-3-amine (1.0 g, 5.9 mmol ) and Pd(dppf)Cl2 (395 mg, 540 umol). The mixture was stirred at 90C for 12 h under N2, cooled to rt and concentrated. The residue was purified by prep-TLC (Si02) followed by prep-HPLC. The eluent was adjusted to pH = 8 with sat.NaHC03 and extracted with ethyl acetate (20 mL chi 3). The combined organic layers was dried over Na2S04, filtered and concentrated under reduced pressure to afford 11-4 (114.9 mg, 337.0 umol, 6.2% yield). M+H+ = 340.2 (LCMS); 1H MR (DMSO-i, 400MHz): delta 9.89 (s, 1H), 9.12 (s, 1H), 8.17 (s, 1H), 8.09 (s, 1H), 7.92 (d, J= 8.6 Hz, 1H), 7.73 (dd, J= 1.5, 8.6 Hz, 1H), 5.67 (s, 1H), 4.63 (br s, 1H), 3.66 (s, 3H), 1.50 (s, 9H).

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-Bromo-1-methyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (159 pag.)WO2018/102751; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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

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

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

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

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

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

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 127107-23-7 as follows. Quality Control of 1-Methyl-1H-pyrazol-4-amine hydrochloride

6-((2,5-dichloropyrimidin-4-yl)(methyl)amino)hexahydrofuro[3,2-b]furan-3-ol (342.2mg, 1.12 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloride (185.0 mg,1.38 mmol) was suspended in n-BuOH (5 mL) and DIPEA (358.8 mg, 2.78 mmol) was added. The resulting reaction was warmed to 150 C and the sealed tube was allowed to react overnight. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (DCM / MeOH (v / v) = 40/1) to give the title compound as a beige solid (156 mg, 38.0%).

According to the analysis of related databases, 127107-23-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Li Xiaobo; Dai Weilong; Wang Tingjin; (74 pag.)CN104926824; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1621-91-6,Some common heterocyclic compound, 1621-91-6, name is 1H-Pyrazole-3-carboxylic acid, molecular formula is C4H4N2O2, 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.

Ste 1: (0582) Preparation of 4-bromo-1H-pyrazole-3-carboxylic acid: (0583) [00241] To a stirred solution of 1H-pyrazole-3-carboxylic acid (2.0 g, 17.85 mmol) in acetic acid (50 mL), bromine (1.2 mL, 23.21 mmol) was added at 0 C and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water (150 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound 4-bromo-1H-pyrazole-3-carboxylic acid (3.4 g, crude) as off-white solid. (0584) Calculated (M+H): 190.94; Found (M+H): 191.0

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

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 35100-92-6, A common heterocyclic compound, 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, molecular formula is C5H9N3, 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 2.01 2- [ [2- [(1 ,5-Dimethylpyrazol-3-yl)aminol -5-(trifluoromethyl)-4-pyridyll aminol -N- methyl-benzamide l,5-Dimethylpyrazol-3-amine (50.6 mg, 0.45 mmol), 2-[[2-chloro-5- (trifluoromethyl)pyridin-4-yl] amino] -N-methylbenzamide (100 mg, 0.30 mmol), sodium te/t-butoxide (43.7 mg, 0.45 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (35.1 mg, 0.06 mmol) and bis(dibenzylideneacetone)palladium (27.8 mg, 0.048 mmol) were suspended in dioxane (3 mL) and the mixture heated at 1500C for 30 minutes in a microwave reactor. The mixture was allowed to cool to room temperature and then loaded onto an SCX column. The mixture was eluted first with MeOH and then with a solution of 7N NH3 in MeOH. Fractions containing product were combined and then evaporated. The residue was purified by preparative HPLC and fractions containing product were combined and evaporated to leave example 2.01 (28.4 mg, 23% yield); 1H NMR spectrum: (300 MHz, DMSO) delta 2.18 (3H, s), 2.77 (3H, d), 3.55 (3H, s), 5.93 (IH, s), 7.08 – 7.11 (IH, m), 7.52 – 7.55 (IH, m), 7.61 – 7.63 (2H, m), 7.69 – 7.72 (IH, m), 8.21 (IH, d), 8.64 (IH, q), 9.36 (IH, s), 10.25 (IH, s); Mass spectrum: m/z (ESI+) (M+H)+ = 405.07.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/153589; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics