Day: July 8, 2021

Adding a certain compound to certain chemical reactions, such as: 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, 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 1260243-04-6, Computed Properties of C6H9N3O2

Example C.22 5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid; a. A mixture of ethyl 3-(4-chloro-phenyl)-3-oxo-propionate (18.1 g, 0.080 mol) and ethyl 5-amino-1H-pyrazole-4-carboxylate (13.7 g, 0.088 mol) was stirred at for 3 h 160 C. Ethyl acetate (40 mL) and hexane (40 mL) were successively added to the cooled mixture and stirring was continued at 0 C. for 0.5 h. The crystals were isolated by filtration and triturated for 1.2 h with 0.2 N HCl (80 mL). The solid was filtered off, washed with water and dried to give ethyl 5-(4-chloro-phenyl)-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylate (13.3 g, 52%). White solid. MS (ISN) 316.3 [(M-H)-]; mp 190-192 C.

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:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2007/72879; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 51105-90-9,Some common heterocyclic compound, 51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, molecular formula is C5H6N2O2, 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.

Step 1: Preparation of Methyl 1-(N,N-dimethylsulfamoyl)-1H-pyrazole-4-carboxylate To a solution of methyl 1H-pyrazole-4-carboxylate (0.3 g, 2.4 mmol) and DBU (0.39 mL, 2.6 mmol) in acetonitrile (12 mL) was slowly added dimethylsulfamoyl chloride (0.27 mL, 2.51 mmol). The reaction mixture was stirred at rt for 1 h and was then concentrated under reduced pressure. The resulting residue was partitioned between water and ethyl acetate. The organic phase was washed with 10% citric acid, water, and brine. The organic phase was dried over MgSO4, filtered, concentrated and purified by silica gel chromatography eluting with a gradient of 5% ethyl acetate in DCM, to provide methyl 1-(N,N-dimethylsulfamoyl)-1H-pyrazole-4-carboxylate (0.54 g), LCMS-ESI (POS.) m/z 310.0 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1H-pyrazole-4-carboxylate, its application will become more common.

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 120068-79-3,Some common heterocyclic compound, 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, molecular formula is C11H5Cl2F3N4, 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 12; To a glass reactor having a central vertical stirrer, a vertical condenser & a dip tube for passing chlorine gas, was charged 730 ml of 3N HC1 in 83.4gm of carbon disulfide, 388gm chlorine gas bubbled over 10 hrs at 24- 25C. Reaction was terminated when carbon disulfide was < 1%. Trichloromethylsulfenyl chloride, 193 gm was obtained after work up & fractionation.Trichloromethylsulfenyl chloride (193 gm) was added in to a mixture of 500 gm water & 100 ml methylene dichloride, along with 83gm Sulfur dioxide gas at 10C, over a period of 4 hrs. Reaction was terminated, when trichloromethyl sulfenyl chloride was <1%. Layer separation gave 228 g of thiophosgene which was added to a stirred mixture of 175 gm activated KF, 1 10 gm ortho-chlorobenzyl chloride and 340 gm spherogel (with 2mm diameter), at 60C, over a period of 3hrs & further maintained at 60C for 2 hrs gave 98% conversion. ortho-Chlorobenzyl trifluoromethylsulfide (138 gms) was isolated by filtration, followed by distillation, which was added to 500 ml methylene chloride, cooled to 0 to 10C & 41 gm chlorine gas was bubbled into it, the reaction was maintained for 2 hrs & then heated slowly to 40-45C. Generated trifluoromethylsulfenyl chloride was passed in to a solution of 5-amino-3-cyano-l-(2,6-dichloro-4- trifluoromethyl phenyl)-pyrazole in methylene dichloride to get 225 g of 5- amino-l-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethyl thiopyrazole. 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-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, its application will become more common. Reference:
Patent; GHARDA, Keki Hormusji; WO2011/107998; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

930-36-9, name is 1-Methylpyrazole, 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. Application In Synthesis of 1-Methylpyrazole

To a solution of 1-methylpyrazole (6.0 g, 73.1 mmol)and N,N,N’,N’-tetramethylethylenediamine (10.96 mL, 73.1 mmol) in THF (125 mL),butyl lithium (2.69 M solution in hexane; 31.8 mL, 85.5 mmol) was added at -78C. The reaction solution was stirred at-78 C. for 30 minutes. Then,cyclohexanone (9.06 mL, 87.7 mmol) was added thereto, and the mixture wasstirred at room temperature for 15 hours. To the reaction solution, water (500mL) was added, followed by extraction with ethyl acetate (250 mL). The thusobtained organic layer was dried over anhydrous sodium sulfate. Afterconcentration under reduced pressure, the residue was purified with silica gelchromatography (hexane/ ethyl acetate=3:2) to yield the title compound (11.32g, 86%) as a colorless oil.

The synthetic route of 930-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daichi Sankyo Corporation; Takahashi, Sakiko; Domon, Yuki; Kitano, Yutaka; Sinojika, Tsuyoshi; (102 pag.)KR2015/126620; (2015); A;,
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 500011-84-7 as follows. SDS of cas: 500011-84-7

Step B: Preparation of 3-BromopyrazoleTo trifluoroacetic acid (70 mL) was slowly added the bromopyrazole product (57.04 g) from Step A. The reaction mixture was stirred at room temperature for 30 minutes and then concentrated at reduced pressure. The residue was taken up in hexane, insoluble solids were filtered off, and the hexane was evaporated to afford the crude product as an oil. The crude product was further purified by chromatography on silica gel using ethyl acetate/dichloromethane (10:90) as eluent to afford an oil. The oil was taken up in dichloromethane, neutralized with aqueous sodium bicarbonate solution, extracted with methylene chloride (3×), dried over magnesium sulfate and concentrated to afford the title product as a white solid (25.9 g), m.p. 61-64 C. 1H NMR (CDCl3) delta 6.37 (d, 1H), 7.59 (d, 1H), 12.4 (br s, 1H).

According to the analysis of related databases, 500011-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E I DU PONT DE NEMOURS AND COMPANY; Lahm, George Philip; McCann, Stephen Frederick; Patel, Kanu Maganbhai; Selby, Thomas Paul; Stevenson, Thomas Martin; US9113630; (2015); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 152120-54-2, A common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, molecular formula is C14H22N4O4, 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.

General procedure: Method B. The required amine hydrochloride salt 7 (1.5-6.0 equiv) and pyrazole-1-carboxamide 6a (1.0 equiv) were dissolved in acetonitrile or chloroform (ca. 1 mL per mmol) and triethylamine (twofold excess based on 7) was added drop-wise with stirring, together with anhydrous MgSO4 to dryness. After 16 h the mixture was filtered, evaporated and purified by column chromatography on silica.

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:
Article; Al Shuhaib, Zainab; Davies, Deiniol H.; Dennis, Mark; Evans, Daniel M.; Fletcher, Matthew D.; Franken, Herjan; Hancock, Paul; Hollinshead, Jackie; Jones, Iestyn; Kaehm, Kristina; Murphy, Patrick J.; Nash, Robert; Potter, David; Rowles, Richard; Tetrahedron; vol. 70; 29; (2014); p. 4412 – 4419;,
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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C3H3BrN2

Production Example 60 A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.19 g of 3-bromopyrazole, 0.55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.31 g of 2-[3-(3-bromopyrazole-1-yl)pyridin-4-yl]-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 59”). [Show Image] 1H-NMR (CDCl3) delta: 8.92 (s, 1H), 8.89 (d, J=5.1 Hz, 1H), 8.16 (d, J=5.1 Hz, 1H), 8.08-8.07 (m, 1H), 7.69 (dd, J=8.8, 1.2 Hz, 1H), 7.66 (d, J=2.4 Hz, 1H), 7. 59 (d, J=8.8 Hz, 1H), 6.57 (d, J=2.4 Hz, 1H)

The synthetic route of 14521-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2274983; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 17635-44-8, 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. 17635-44-8 name is 3,4,5-Tribromopyrazole, 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.

To a solution of 3,4,5-tribromo-1 /-/-pyrazole (21 g, 69 mmol) in THF (200 mL) were added tetrahydro-2H-pyran-3-ol (8.5 g, 83 mmol), PPh3(36 g, 138 mmol), DIAD (27 g, 138 mmol) at 0 C. The resulting mixture was stirred at 0 C for 3 hrs. The mixture was poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous Na2S04and concentrated. The crude was purified by column chromatography on silica gel (PE: EtOAc= 10: 1 ) to give the title compound as oilsolid (10 g, yield 50%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4,5-Tribromopyrazole, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DING, Xiao; HO, Ming-Hsun; REN, Feng; YU, Haihua; ZHAN, Yang; (290 pag.)WO2019/12093; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H5IN2

1-Methyl-4-((trimethylsilyl)ethynyl)-1 W-pyrazole (19); [00204] 1 -Methyl-4-iodo-pyrazole (18) (5.0g 24.04mmole) was dissolved in DMF (32ml_) and ethynyltrimethylsilane (4.76ml_, 3.31 g, 33.7mmole) was added followed by diisopropylamine (4.46ml_, 3.21 g 31 .78mmole), copper(l) iodide (304mg 1 .59mmole) and triphenylphosphine (1 .26g 4.81 mmole). The reaction was flushed with argon. Palladium acetate (351 mg 1 .56mmole) was added and the reaction was again flushed with argon. It was heated at 60C for 60 mins. The reaction was cooled, added to water (350ml) and extracted with ether (3x100ml_). The organic solution was filtered from a brown solid which was washed with a little more ether. The organic solution was washed with water (3x80ml_), brine, dried and evaporated. The crude product was flash chromatographed (silica) using 1 :4 ethyl acetate:cyclohexane and then 1 :3 ethyl acetate:cyclohexane to give the title compound as a solid (2.85g 67%). 1 H-NMR (CDCI3, 500MHz): delta 0.24 (s, 9H), 3.87 (s, 3H), 7.50 (s, 1 H), 7.58 (s, 1 H).

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 39806-90-1.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 3920-50-1, name is Pyrazole-3-carboxaldehyde, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 3920-50-1

1.18 g (20 mmol) of hydroxylamine hydrochloride, 1.63 g (20 mmol) of sodium acetate and 40 ml of ethanol were added to a 100 ml three-necked flask, and 0.96 g (10 mmol) of 3-formaldehyde pyrazole was added thereto with stirring. The temperature was raised to 50 C and the reaction was carried out for 2 h. After the reaction, a milky white turbid liquid was obtained, which was cooled to room temperature, filtered, and the filtrate was evaporated to give an oily viscous solid. Dissolved in 50 ml of water, The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated to dryness to give a pale yellow viscous solid, 0.94 g. The yield was 85.3%.

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 3920-50-1.

Reference:
Patent; Xi’an Modern Chemical Institute; Zhang Yiying; Chang Pei; Hu Jianjian; Sun Chenghui; Pang Siping; (6 pag.)CN109251174; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics