Simple exploration of Ethyl 5-amino-1H-pyrazole-3-carboxylate

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.

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;,
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Share a compound : C10H10N2

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.

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);,
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Continuously updated synthesis method about 3-Iodo-1-methyl-1H-pyrazole

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 92525-10-5.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Iodo-1-methyl-1H-pyrazole

Step 1. Synthesis of 5-fluoro-3-iodo-1-methyl-1H-pyrazole (C27) Lithium diisopropylamide (2.0 M in heptane/tetrahydrofuran/ethylbenzene, 3.30 mL, 6.60 mmol) was added drop-wise to a -75 C. solution of 3-iodo-1-methyl-1H-pyrazole (97%, 1.29 g, 6.02 mmol) in tetrahydrofuran (25 mL). After 5 minutes, N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (97%, 2.60 g, 8.00 mmol) was added to the cold solution in one portion. The reaction mixture was allowed to warm to 0 C. over 30 minutes, and was then quenched with saturated aqueous ammonium chloride solution (25 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (15 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane) afforded the product as a pale yellow oil. Yield: 435 mg, 1.92 mmol, 32%. GCMS m/z 226 [M+]. 1H NMR (400 MHz, CDCl3) delta 5.93 (d, J=6.0 Hz, 1H), 3.74 (d, J=1.2 Hz, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 92525-10-5.

Reference:
Patent; Pfizer Inc.; Brodney, Michael Aaron; Butler, Christopher Ryan; Beck, Elizabeth Mary; Davoren, Jennifer Elizabeth; LaChapelle, Erik Alphie; O’Neill, Brian Thomas; US2014/228356; (2014); A1;,
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Extracurricular laboratory: Synthetic route of 1152582-56-3

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.

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

Application of 2458-26-6

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

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;,
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Extended knowledge of 26621-44-3

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.

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

Extended knowledge of 28466-26-4

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-Aminopyrazole, other downstream synthetic routes, hurry up and to see.

Application of 28466-26-4, The chemical industry reduces the impact on the environment during synthesis 28466-26-4, name is 4-Aminopyrazole, I believe this compound will play a more active role in future production and life.

To a solution of 1 H-pyrazol-4-amine (1 g, 95% purity, 11 .4 mmol) in acetonitrile (57 mL) were added (bromomethyl)cyclopropane (1.65 ml, 17.1 mmol, GAS-RN 7051-34-5),powdered potassium carbonate (3.95 g, 28.6 mmol), and triethylamine (2.39 mL,17.1 mmol). The mixture was heated to 900 for 4h and stirred at room temperatureovernight. For work-up, it was filtered, and the solid was rinsed with ethyl acetate.Goncentration of the filtrate in vacuo followed by flash chromatography led to N(cyclopropylmethyl)-1 H-pyrazol-4-amine (416 mg, 24% yield, 90% purity).LG-MS (Method B): Rt = 0.54 mm; MS (ESIpos): m/z = 138 (M÷H)1HNMR (400MHz, DMSO-d6) oe [ppm]: 0.16 (m, 2H), 0.42 (m, 2H), 0.99 (m, 1H), 2.68 (m,2H), 4.23 (m, 1H), 7.03 (5, 2H), 12.01 (5, 1H).As additional fraction, N, N-bis(cyclopropylmethyl)- 1 H-pyrazol-4-am me was isolated(657 mg, 27% yield, 90% purity).LG-MS (Method B): Rt = 0.97 mm; MS (ESIpos): m/z = 192 (M÷H)1HNMR (400MHz, DMSO-d6) oe [ppm]: 0.06 (m, 4H), 0.33 (m, 4H), 0.84 (m, 2H), 2.82 (d,4H), 7.07 (5, 2H), 12.07 (5, 1H).

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-Aminopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; CLEVE, Arwed; (139 pag.)WO2018/210729; (2018); A1;,
Pyrazole – Wikipedia,
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The important role of 110860-60-1

The synthetic route of 110860-60-1 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. 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

The origin of a common compound about 92525-10-5

The synthetic route of 92525-10-5 has been constantly updated, and we look forward to future research findings.

Electric Literature of 92525-10-5, These common heterocyclic compound, 92525-10-5, name is 3-Iodo-1-methyl-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.

3-Iodo-1-methyl-1H-pyrazole (2.19 g, 10.5 mmol) was added dropwise to iPrMgCl.LiCl (10.8 mL, 14.0 mmol, 1.3 M THF solution) and THF (14 mL) cooled to 0 C. under a nitrogen atmosphere. The mixture was allowed to stir at room temperature for 1 h. N-Methoxy-N,1-dimethylcyclopentane-1-carboxamide (1.2 g, 7.0 mmol) was then added dropwise. The mixture was stirred at room temperature for 18 h and then was quenched with saturated aqueous NH4Cl. The reaction mixture was extracted with EtOAc. The organic extract was dried (Na2SO4) and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (10-50% EtOAc/heptane) to afford 992 mg (74%) of the title compound. LCMS 172.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.34 (d, J=2.3 Hz, 1H), 6.81 (d, J=2.3 Hz, 1H), 3.98 (s, 3H), 2.46-2.33 (m, 2H), 1.79-1.63 (m, 6H), 1.49 (s, 3H).

The synthetic route of 92525-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Gerstenberger, Brian Stephen; Flick, Andrew Christopher; Lombardo, Vincent Michael; Mousseau, James John; Nuhant, Philippe Marcel; Robinson, JR., Ralph Pelton; Schnute, Mark Edward; Kung, Daniel Wei-Shung; Schmitt, Daniel Copley; Thorarensen, Atli; Trujillo, John Isidro; Unwalla, Rayomand Jal; Wu, Huixian; (104 pag.)US2020/95239; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

A new synthetic route of 120068-79-3

The synthetic route of 120068-79-3 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. 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C11H5Cl2F3N4

EXAMPLE 4 Production of N-[3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole-5-yl]pyrazine-2-carboxamide Into a mixture of 0.5 g (1.6 mmol) of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole-3-carbonitrile, 0.24 g (1.7 mmol) of methyl pyrazinecarboxylate, and 0.5 ml of acetonitrile was gradually added 0.3 g (1.6 mmol) of 28% CH3ONa/CH3OH at room temperature. After 2 hours of stirring at room temperature, 5 ml of water and then concentrated hydrochloric acid were added thereto to make the mixture pH 2, whereby crystals were precipitated. Thereto was added 10 ml of ethyl acetate, followed by extraction. The organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. After removal of the sodium sulfate by filtration, the layer was concentrated and the resulting crystals were filtrated. The crystals were washed with a small amount of hexane and ethyl acetate and the dried to obtain 0.5 g (yield 77%) of N-[3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole-5-yl]pyrazine-2-carboxamide.

The synthetic route of 120068-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUBISHI CHEMICAL CORPORATION; US2003/60471; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics