Tag: M.W:100-200

Synthetic Route of 3469-69-0, 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. 3469-69-0 name is 4-Iodopyrazole, 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.

4-Iodo-1H-pyrazole (5.0 g, 25.8 mmol) was dissolved in DMF (50 mL), and K2C03 (4.27 g, 30.9 mmol) was added followed by 1-(chloromethyl)-4-methoxybenzene (3.86 mL, 28.4 mrnol). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then poured into water and extracted with Et20, washed with brine, dried over sodium sulfate, filtered and concentrated to afford 4-iodo-i-(4-methoxybenzyl)-lH-pyrazole (8.3 g, 26.4 mmol, 103 % yield).

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

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (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. 110860-60-1, name is Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 110860-60-1

9.2 g of the intermediate (b) obtained in the above-described Synthesis Example 1-1 is dissolved in a mixed solution of 55 mL of acetic acid and 37 mL of propionic acid at room temperature. The resulting solution is cooled with ice to an internal temperature of -3C, and a 40% by weight solution of nitrosylsulfuric acid in sulfuric acid is dropwise added thereto over 10 minutes at an internal temperature of -3C to 4C. After stirring the mixture at an internal temperature of 4C for 1 hour, 0.2 g of urea is added thereto. Thereafter, the mixture is cooled to an internal temperature of-3C, followed by stirring for further 10 minutes to obtain a diazonium salt solution. Separately, 10 g of the intermediate (d) obtained in the above-described Synthesis Example 1-1 is completely dissolved in 150 mL of acetone, and the solution is cooled to an internal temperature of 17C and added to the above-described diazonium salt solution over 25 minutes at an internal temperature ranging from -3C to 3C. After completion of the addition, the mixture is stirred at 3C for 30 minutes, and the ice bath is removed to allow the temperature of the mixture to rise to room temperature over 30 minutes. After stirring the mixture at room temperature for 30 minutes, crystals obtained are collected by filtration, spray washed with 150 mL of acetone, then with 100 mL of water. Crystals obtained are suspended in 400 mL of water without drying, and a 8N potassium hydroxide aqueous solution is added thereto to adjust the pH to 5.7. After stirring the mixture at room temperature for 25 minutes, crystals obtained are collected by filtration, sufficiently spray washed with water. The thus-obtained crude pigment (1)-1 is dried at room temperature for 12 hours. The thus-obtained crude pigment (1-I) is suspended in a mixed solvent of 580 mL of acetone and 1160 mL of water, followed by stirring for 30 minutes under reflux. Thereafter, the mixture is cooled to room temperature over 10 minutes, followed by stirring at room temperature for 5 hours to obtain 17,6 g of beta-type crystal form azo pigment (1)-1 having the crystal form of the invention and represented by formula (1). Yield: 91.0% Visual observation of the thus-obtained beta-type crystal form azo pigment (1)-1 with a transmission microscope (manufactured by JEOL Ltd.; JEM-1010; electron microscope) reveals that the length of the long axis of primary particles is about 150 nm. When X-ray diffraction of the beta-type crystal form azo pigment (1)-1 is measured under the aforesaid conditions, characteristic X-ray peaks are shown at Bragg angles (2theta+/-0.2) of 7.0, 26.4, and 27.3. The X-ray diffraction pattern with characteristic Cu Kalpha line is shown in Fig. 10.

The synthetic route of 110860-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; EP2343343; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 26621-44-3, name is 3-Nitro-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 26621-44-3, Formula: C3H3N3O2

To a solution of compound 1 (25.0 g, 0.22 mol, 1.0 eq) in THF (250 mL) under Ar protection was added NaH (60%, 9.7 g, 0.24 mol, 1.1 eq) in portions.After stirring at room temperature for 10 min, SEMCl (44.2 g, 0.27 mol, 1.2 eq) was added dropwise.Stir overnight at room temperature.The reaction was quenched with saturated aqueous NH4Cl.The reaction solution was diluted with EtOAc, washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure.Purification by column (PE / EtOAc = 5/1) gave compound 2 (36.3 g, 67%) as a white solid.

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

Reference:
Patent; Longtaishen Pharmaceutical (Nanjing) Co., Ltd.; Yang Lei; (45 pag.)CN110590747; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

2458-26-6, name is 3-Phenyl-1H-pyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H8N2

General procedure: Methyl 3-(3-phenyl- 1 H -pyrazol- 1 -yljpropanoate Synthesised using the general procedure for Michael addition. General Synthetic Procedures and Characterisation Michael Addition 3-Phenyl-1 H-pyrazole (1 .73 mmol), acrylate (5.20 mmol) and DBU (130 muIota, 0.87 mmol) were combined in acetonitrile (3.5 ml), under nitrogen. The reaction was stirred at 50 C for 18 h and monitored by TLC. Once complete all of the volatiles were removed in vacuo and the crude material was purified by column chromatography, eluting with 15-25% ethyl acetate/petroleum spirits to obtain the desired product. Methyl 3-(3-phenyl- 1 H -pyrazol- 1 -yljpropanoate Synthesised using the general procedure for Michael addition.

The synthetic route of 2458-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MONASH UNIVERSITY; THE UNIVERSITY OF WESTERN AUSTRALIA; BAELL, Jonathan; PIGGOTT, Matthew; RUSSELL, Stephanie; TOYNTON, Arthur; RAHMANI, Raphael; FERRINS, Lori; NGUYEN, Nghi; (178 pag.)WO2015/172196; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1152582-56-3, 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 1152582-56-3 as follows.

Example 22 N-(5-(4-fluorophenyl)-11-methyl-1-oxo-2,4,5,11-tetrahydro-1H-2,5,6,11-tetraazadibenzo[cd,h]azulen-8-yl)-2-(1-methyl-1H-pyrazol-4-yl)acetamide [0706] A stock solution of Example 14e and N,N-diisopropylethylamine (0.11 M and 0.33 M in N,N-dimethylacetamide, respectively, 350 muL, 0.038 mmol Example 14e and 0.11 mmol N,N-diisopropylethylamine), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.13 M in N,N-dimethylacetamide, 350 muL, 0.046 mmol), and 2-(1-methyl-1H-pyrazol-4-yl)acetic acid (0.40 M in N,N-dimethylacetamide, 113 muL, 0.050 mmol) were aspirated from their respective source vials, mixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 100 C., and passed through the reactor at 180 muL per minute (10 minute residence time). Upon exiting the reactor, the reaction mixture was loaded directly into an injection loop and purified by reverse phase HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) to yield the title compound as an impure mixture. The material was dissolved in methanol (1 mL) and manually injected into the HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) give 0.0067 g (38%) of the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) delta 8.49 (d, J=2.44 Hz, 1H), 8.45 (d, J=2.75 Hz, 1H), 7.77 (s, 1H), 7.63 (s, 1H), 7.40 (s, 1H), 7.07 (s, 1H), 6.87 (m, 2H), 6.57 (m, 2H), 4.60 (m, 2H), 4.07 (s, 3H), 3.81 (s, 3H), 3.55 (s, 2H). MS (APCI+) m/z 484.1 (M+H)+.

According to the analysis of related databases, 1152582-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu, Dachun; Pratt, John; Wang, Le; Hasvold, Lisa A.; Bogdan, Andrew; US2014/256710; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1128-54-7, name is 3-Methyl-1-phenyl-1H-pyrazole, molecular formula is C10H10N2, 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. Safety of 3-Methyl-1-phenyl-1H-pyrazole

General procedure: To a stirred solution of 1-phenyl-1H-pyrazole (5a) (288 mg, 2.00 mmol, 1.00 equiv.) in dryTHF (2.00 mL/mmol based on 5a), 1.64 M solution of n-BuLi in n-hexane (1.34 mL, 2.20mmol, 1.10 equiv.) was added dropwise at -78 C under an argon atmosphere. After being stirred at the same temperature for 1 h, benzoyl chloride (6a) (0.260 mL, 2.20 mmol, 1.10equiv.) was added to the mixture. After being warmed to room temperature and stirred at the same temperature for 18 h, the reaction mixture was quenched with saturated NH4Cl aq. The aqueous layer was extracted with ethyl acetate. The combined extract was washed with brine,dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel with hexane : EtOAc = 5 : 1 to give phenyl(1-phenyl-1H-pyrazol-5-yl)methanone (7a) as a white solid (429 mg, 1.73 mmol, 86%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1128-54-7, its application will become more common.

Reference:
Article; Fuse, Shinichiro; Kadonosono, Tetsuya; Kizaka-Kondoh, Shinae; Kuchimaru, Takahiro; Nakamura, Hiroyuki; Sato, Shinichi; Suzuki, Kensuke; Ueda, Hiroki; Bioorganic and medicinal chemistry; (2019);,
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 105434-90-0 as follows. Application In Synthesis of Ethyl 5-amino-1H-pyrazole-3-carboxylate

[00383] To a solution of ethyl 5-amino-1H-pyrazole-3-carboxylate (1.55 g, 10 mmol) in AcOH (20 mL) was added 4,4,4-trifluoro-1-(4-methoxyphenyl)butane-1,3-dione (2.71 g, 11 mmol). The mixture was refluxed for 5 h and subsequently cooled down to 0 C in an ice bath. The precipitate was collected by filtration and recrystallized by hexanes/ethyl acetate to give a yellow solid. The solid was taken in MeOH (20 mL) and NaOH aq. (1M, 20 mL), and the solution was stirred at room temperature for 5 h. The solvent was then removed and the residue was acidified by 1M HC1 until PH 2. The precipitate was collected by filtration, and washed with cold water. The resulting solid was dried to obtain the pure product as a pale yellow solid (1.55 g, 92% yield). ?H NMR (400 MHz, DMSO-d6) oe 13.57 (s, 1H), 8.26-8.22 (m, 3H), 7.39 (d, J = 7.9 Hz, 2H), 7.32 (s, 1H), 2.39 (s, 3H).

According to the analysis of related databases, 105434-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford D.; YUAN, Yiyuan; ZHANG, Yongyou; READY, Joseph; HU, Bin; (228 pag.)WO2018/145080; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 2075-46-9, 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. 2075-46-9, name is 4-Nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 4-nitro-1H-pyrazole (1.13 g, 10 mmol) in DMF (20 ml) was added K2CO3 (1.38 g, 10 mmol) and 2-Bromoethanol(1.50 g, 12 mmol). Then the mixture was stirred at 60 C for 12 h. DMF was removed at reduced pressure and add water (100 ml), extractedwith ethyl acetate (3×100 ml), dried with Na2SO4 and evaporated to give compound 2a as a white solid.

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

Reference:
Article; Ding, Huai-Wei; Wang, Shu; Qin, Xiao-Chun; Wang, Jian; Song, Hong-Rui; Zhao, Qing-Chun; Song, Shao-Jiang; Bioorganic and Medicinal Chemistry; vol. 27; 13; (2019); p. 2729 – 2740;,
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. 473528-88-0, name is 4-Bromo-1-methyl-1H-pyrazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C5H5BrN2O

Steps 1-2 (0865) To a mixture of 22 6-bromoisoquinolin-3-amine (XII) (4.0 g, 17.93 mmol), Pd(dppf)Cl2-CH2Cl2 adduct (1.03 g, 1.26 mmol), 174 KOAc (4.39 g, 44.83 mmol) and 175 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (5.01 g, 19.72 mmol) in 33 1,4-dioxane (50 mL) was bubbled with 176 N2 for 2 min. The reaction mixture was sealed and heated at 90 C. for 1.5 h. The reaction was cooled to room temperature, filtered and washed with EtOAc. The filtrate was concentrated and the residue taken in dioxane (50 mL). To the suspension was added 177 4-bromo-2-methyl-pyrazole-3-carbaldehyde (LX) (3.39 g, 17.93 mmol) followed by 32 K3PO4 (9.52 g, 44.83 mmol), Pd(dppf)Cl2-CH2Cl2 adduct (1.03 g, 1.26 mmol) and 24 water (15 mL). The mixture was purged with N2 for a min, sealed and heated again at 90 C. for 19 h. The mixture was cooled to room temperature and concentrated to about 20 mL. The concentrate was diluted with EtOAc and filtered through a pad of Celite. The filtrate was diluted with water and the organic layer separated. The organic layer was washed with brine; dried, filtered and concentrated. The residue was triturated in ether and the resulting solid filtered to afford 178 4-(3-amino-6-isoquinolyl)-2-methyl-pyrazole-3-carbaldehyde (LXI) (4.1 g, 16.2 mmol, 90.6% yield) as a brown solid. 1H NMR (499 MHz, DMSO-d6) delta ppm 0.01 (6H, s), 0.86 (9H, s), 0.88-1.00 (2H, m), 1.23-1.35 (2H, m), 1.35-1.46 (1H, m), 1.69-1.79 (2H, m), 1.85-1.95 (2H, m), 2.21 (1H, tt, J=12.21, 3.57 Hz), 3.38 (2H, d, J=6.31 Hz), 3.57 (3H, s) ESIMS found for C14H12N4O m/z 252.95 (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; Samumed, LLC; KC, Sunil Kumar; Mittapalli, Gopi Kumar; Hofilena, Brian Joseph; Marakovits, Joseph Timothy; Chiruta, Chandramouli; Mak, Chi Ching; Cao, Jianguo; (324 pag.)US2017/313681; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 52222-73-8, name is 4-(Trifluoromethyl)-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. COA of Formula: C4H3F3N2

To a vial was added 3-iodo-N- isopropyl-l-[(4-methoxyphenyl)methyl]pyrazolo[4,3-c]pyridin-4-amine (100 mg, 0.237 mmol), 4-(trifiuoromethyl)-lH-pyrazole (30.6 mg, 0.225 mmol), copper(I) iodide (11.3 mg, 0.059 mmol), potassium carbonate (57.8 mg, 0.414 mmol). The vial was purged with nitrogen and toluene (0.47 mL, 4.45 mmol) and iras-N,N’-dimethylcyclohexane-l,2- diamine, (0.02 mL, 0.12 mmol) were added. The vial was sealed and heated to 110 C for 24 h. The reaction mixture was filtered through Celite, eluting with DCM and concentrated in vacuo. The crude residue was purified by column chromatography (0-20% EtOAc in DCM) to give the title compound which was used directly in the next step.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHAN, Bryan; ESTRADA, Anthony; SHORE, Daniel; SWEENEY, Zachary; WO2013/139882; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics