Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 948570-75-0, name is 1-(2-Methoxyethyl)-4-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 948570-75-0, HPLC of Formula: C6H9N3O3

A par flask was charged with 1-(2-Methoxy-ethyl)-4-nitro-1H-pyrazole 16 (2.5 g, 14.60 mmol) in EtOH (250 mL) followed by addition of Pd-C (20% w/w, 0.50 g). The flask was evacuated under vacuum and then purged with hydrogen. The reaction was stirred under hydrogen atmosphere (1 atm) for 1 6h. After the completion of reaction, the solution was filtered through sintered funnel with a pad of celite, washed with methanol and concentrated under reduced pressure to afford precursor-06 (2.0 g, 97% yield) that was taken as such for the next step without any further purification. ?H NMR (400 MHz,CDC13): 6 7.03 (s, 1H), 6.89 (s, 1H), 4.19-4.17 (t, 2H), 3.78 (br s, 2H), 3.67-3.64 (t, 2H), 3.21 (s, 3H). MS: 142.11 (M+H).

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, 1-(2-Methoxyethyl)-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, 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. Formula: C5H5N3O4

Preparative Example 7 4-nitro-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester 340 mg (1.99 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.33 ml (2.19 mM) of iodomethane and 1.3 g (3.98 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 195 mg (53%) of the title compound and 110 mg (30%) of the compound of Preparative Example 13. 1H NMR (300 MHz, CDCl3) delta 4.00 (s, 3H), 4.02 (s, 3H), 8.15 (s, 1H). Mass: 185 (M+) ; 340 mg (1.99 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.33 ml (2.19 mM) of iodomethane and 1.3 g (3.98 mM) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 110 mg (30%) of the title compound and 195 mg (53%) of the compound of Preparative Example 7.1H NMR (300 MHz, CDCl3) delta 4.03 (s, 3H), 4.04 (s, 3H), 8.03 (s, 1H).

The synthetic route of 138786-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; US2010/63106; (2010); 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 42027-81-6 as follows. Recommanded Product: 2-(4-Nitro-1H-pyrazol-1-yl)ethanol

Into a 100 mL round-bottom flask purged and maintained under inert atmosphere of nitrogen, were placed compound 33.1 (500 mg, 3.18 mmol, 1.00 equiv) in 10 mL of distilled DMF. This was followed by the addition of sodium hydride (191 mg, 7.96 mmol, 1.50 equiv) in portions. After stirring for 30 mm, Mel (2.26 g, 15.92 mmol, 5.00 equiv) was added dropwise via syringe and the resulting solution was stirred for 16 h at room temperature. The reaction was then quenched with 50 mL of water, extracted with 3 x 60 mL of ethyl acetate. The organic layers were combined and washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified using flash column chromatography to furnish 420 mg (77%) of intermediate 33.2 as a yellow solid.

According to the analysis of related databases, 42027-81-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); 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. 1572-10-7, name is 3-Amino-5-phenylpyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 1572-10-7

General procedure: The compound tetronic acid (15) (80 mg, 0.8 mmol) was dissolved in 4 mL of ethanol, followed by addition of terphenyl aldehyde 13a (221.2 mg, 0.8 mmol) and 3-amino-5-phenyl pyrazole 14a (127.2 mg, 0.8 mmol). The reaction mixture was refluxed in ethanol at 78 C for an hour. Then reaction suspension was cooled to room temperature, and the precipitated product was collected by vacuum filtration and washed with ethanol (3 mL), then recrystallized from ethanol to afford pure compound 8a as a white solid, 340 mg in 85% yield. Mp: 273-274 C; 1H NMR (300 MHz, DMSO-d6): delta 4.80 (s, 2H), 5.25 (s, 1H ), 6.89-6.99 (m, 1H), 7.19-7.35 (m, 7H), 7.42-7.52 (m, 4H), 7.65 (dd, 4H, J = 8.8, 11.7 Hz), 8.05 (s, 1H), 10.19 (s, 1H ), 12.56 (s, 1H); 13C NMR (300 MHz, DMSO-d6): delta 30.5, 64.8, 94.4, 99.8, 111.1, 111.3, 113.2, 121.3, 125.4, 126.1, 126.7, 126.9, 127.1, 127.2, 127.3, 128.3, 128.7, 128.8, 132.7, 137, 137.2, 138.8, 139.3, 145.8, 152.7, 157.7, 172.2; MS (ESI): 500 [M+H]+; HRMS (ESI) calcd for C32H23O2N3F [M+H]+ 500.1712; found: 500.1738.

The synthetic route of 1572-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Tamboli, Jaki R.; Lakshma Nayak; Adil; Vishnuvardhan; Ramakrishna; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2714 – 2723;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, 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 660845-30-7, Formula: C6H5ClF2N2O

Preparation example 1 : preparation of N-cyclopropyl-N-[2-(2,6-dichlorophenoxy)ethyl]-3-(difluoromethyl)- 5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound 124)Step 1 : preparation of of 5-chloro-3-(difluoromethyl)-1-methyl-1 H-pyrazole-4-carboxylic acid (llla-1 ) In a 500 ml flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-1-methyl-1 H-pyrazole-4-carbaldehyde are added to 30 ml of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6ml of water is added to the reaction mixture, followed by 103 ml of a 30% solution of hydrogen peroxide in water, whilst keeping the temperature below 37C. After the end of the addition, the reaction mixture is stirred at 50C for 7 hours. Once the reaction mixture is back to room temperature, the two phases are separated and the organic phase is extracted with 100 ml of water. The combined aqueous phases are acidified to pH 2 with aqueous hydrochloric acid. The resulting white precipitate is filtered, washed twice with 20 ml of water, and dried to yield 3.2 g of 5-chloro-3-(difluoromethyl)-1-methyl-1 H-pyrazole-4-carboxylic acid as a white solid. H NMR (400 MHz, DMSO-c/6) delta ppm : 3.78 (s, 3H); 7.12 (t, 1 H, JHF = 53.60 Hz)13.19 (s, 1 H); IR (KBr) : 1688 cm”1 (C=0); 2200-3200 cm”1 broad (hydrogen bond).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; BENTING, Juergen; COQUERON, Pierre-Yves; CRISTAU, Pierre; DAHMEN, Peter; DESBORDES, Philippe; GARY, Stephanie; GREUL, Joerg; HADANO, Hiroyuki; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; WO2011/151370; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 18213-75-7, A common heterocyclic compound, 18213-75-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, molecular formula is C5H8N4O, 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.

5-Amino-I-methyl-I H-pyrazole-4-carboxylic acid amide (1.49 g; 10.618 mmol and 4,4-dimethyl-dihydro-pyran-2,6-dione (2.26 g; 15.898 mmol) was heatedto 170 C for 6 h. The reaction mixture was cooled to room temperature, 10% aqueous sodium hydroxide solution (56.00 mL) was added and the mixture was heated to 100 C for 2h. The reaction mixture was cooled to 0 C, acidified with acetic acid and extracted with dichloromethane. The combinedorganic layers were dried with sodium sulfate, filtered by suction and concentrated. The residue was triturated with petrol ether and ethyl acetate (1/I), the resulting solid was filtered and dried. Yield: 0.80 g (28%) colorless solid: LC/MS (B), Rt: 1.84 mm; (M+H) 265.0. ?H NMR (400 MHz, DMSO-d6) 6 13.00 (brs, IH), 12.12 (brs, IH), 7.92 (s, IH), 3.86 (s, 3H), 2.68 (5, 2H), 2.22(s, 2H), 1.04 (s, 6H)

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; MERCK PATENT GMBH; BUCHSTALLER, Hans-Peter; DORSCH, Dieter; (111 pag.)WO2017/76484; (2017); 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. 2075-45-8, name is 4-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 2075-45-8

4-Bromo-1-(1-ethoxyethyl)-1H-pyrazole (5-II-a) To a solution of 4-bromo-1H-pyrazole (3 g, 20.4 mmol), ethyl vinyl ether (1.76 g, 24.5 mmol) in DCM (30 mL) was added HCl (4M in dioxane, 0.16 mL), and the reaction mixture was stirred for 3 h at RT. After completion of the reaction (monitored by TLC), the reaction was neutralized with saturated NaHCO3 solution and extracted with DCM (3*100 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to afford 5-II-a (4.46 g, 89%) as colorless liquid; TLC: 30% EtOAc/Hexane (Rf: 0.7); 1H-NMR (CDCl3, 200 MHz): delta 7.60 (s, 1H), 7.46 (s, 1H), 5.46 (q, J=6.0 Hz, 1H), 3.55-3.25 (m, 2H), 1.63 (d, J=6.0 Hz, 3H), 1.15 (t, J=7.2 Hz, 3H); MS: 221 [M++2].

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; Petter, Russell C.; Jewell, Charles F.; Lee, Kwangho; Medikonda, Aravind Prasad; Niu, Deqiang; Qiao, Lixin; Singh, Juswinder; Zhu, Zhendong; US2011/269244; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 34334-96-8, 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. 34334-96-8, name is 3-Methyl-5-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Add acetonitrile (75 rnL) to a mixture of (2.0 g, 15rnmoi). potassium carbonate (4.1 g, 2.0 eq), and 1-chioro-2-propanol (3.8 mL, 3.0 eq).Stir at 85 C overnight. Cool to rt. Filter and rinse the solids with EtOAc. Concentrate the filtrate in vacuo to provide a residue. Subject the residue to normal phase chromatography, eluting with 50% EtOAc in hexanes, to give the title compound (2.0 g, 65%). MS (ES) ,n/z 186 (M+1-1).

The synthetic route of 3-Methyl-5-nitro-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; BASTIAN, Jolie Anne; CLAYTON, Joshua Ryan; COATES, David Andrew; SALL, Daniel Jon; WOODS, Timothy Andrew; (58 pag.)WO2018/13486; (2018); 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. 89202-89-1, name is 1,4-Dimethyl-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O2

1,4-Dimethyl-1H-pyrazole-3-carbonyl chloride 1,4-Dimethyl-1H-pyrazole-3-carboxylic acid (190 mg) was weighed to a round bottom flask and thionyl chloride (1 ml) was added. The reaction was heated to reflux for 6 h then overnight at RT. After this time thionyl chloride was evaporated and the residue azeotroped with toluene to afford the title compound, 200 mg. 1H NMR (CDCl3) delta 7.2 (m, 1H), 3.98 (s, 3H), 2.27 (s, 3H).

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; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 118430-73-2, name is 3-(tert-Butyl)-1-methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 118430-73-2

Pyrazole 5 (673 mg, 4.4 mMol), diisopropylethylamine (684 mg, 5.3 mMol, 1.2 eq.), and DCM (9 mL) were cooled to -10 C. and phenyl chloroformate (750 mg, 4.8 mMol, 1.1 eq.) was added in a single portion. The solution was allowed to warm to 0 C. and stir for 30 min. The solution was partitioned between ether and aqueous sodium bicarbonate and the ether layer was washed with brine. The organic fraction was dried over anhydrous sodium sulfate and the solvent removed in vacuo and the residue purified using silica gel chromatography eluting with ethyl acetate (5%-50%)/hexane. Solvent removal afforded the product (6) as brittle foam (1.0 g, 3.9 mMol, 90% yield), which provided a single peak by LC-MS analysis (M+H=274.1). 1H NMR (400 MHz, CDCl3) delta: 7.4 (dd, J=8.0, 7.6 Hz, 2H), 7.25 (tt, J=7.6 Hz, 1H), 7.18 (d, J=8.0 Hz, 2H), 6.95 (brs, 1H), 6.15 (s, 1H), 3.79 (s, 3H), 1.29 (s, 9H).

The synthetic route of 118430-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Holtzman, Michael; Romero, Arthur; Alevy, Yael; Patel, Anand; Brett, Thomas; Patel, Dhara; US2015/183777; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics