Tag: M.W=0-100

Synthetic Route of 1192-21-8, A common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, molecular formula is C4H7N3, 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.

in two screw-top glass pressure vessels, split and combine the following amounts in two equal portions 2-(2-chioro-4-pyridyi)-5-(2-nethoxyethyi)-6,6-dimethyi-thieno[2,3- c]pyrroi-4-one (13 g, 38.59 mmol), 1-methyi-5-aminopyrazole (11.245 g, 115.78 mmoi),cesium carbonate (37.724 g, 115.78 mrnol), 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (2.010 g, 3.47 mmoi), paiiadium(ii)acetate (520 mg, 2.32 nmoi) and 1,4-dioxane (350 mL). Seal each vessel and heat at 110 °C overnight.Dilute the reaction mixture with 10percent MeOH in DCM (2 L) and wash the resulting solution with saturated NaC1. Back extract the aqueous solution with DCM and combinethe organic solutions. Dry the combined solutions over a mixture of an hyous sodium sulfate and aithydrous magnesium sulfate, filter and concentrate the filtrate under reduced pressure. Purify by silica gel chromatography by loading the residue onto a 260 g loading coiunm with DCM and then eluting the loading coiunm onto a 750 g silica gel column with a gradient of 60-100percent of 10percent MeOH in EtOAc in hexane to yield the titlecompound 8.4 g (55percent). MS rn/z): 398 (M+i).

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; ELI LILLY AND COMPANY; CORTEZ, Guillermo S.; JOSEPH, Sajan; MCLEAN, Jonathan Alexander; MCMILLEN, William T.; RODRIGUEZ, Michael John; ZHAO, Gaiying; (70 pag.)WO2016/106009; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 35277-02-2, name is 4-Fluoro-1H-pyrazole, molecular formula is C3H3FN2, 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. Quality Control of 4-Fluoro-1H-pyrazole

(5)-N-(2-Chloropyridin-4-yl)-3-(4-fluoro- lH-pyrazol- l-yl)-2-hydroxy-2-methylpropanam (0881) (0882) 1041 (0883) [00407] To a dry, nitrogen-purged 100 mL round-bottom flask equipped with a dropping funnel under argon atmosphere, NaH of 60% dispersion in mineral oil (96 mg, 2.4 mmol) was added in 10 mL of anhydrous THF solvent at ice-water bath. 4-Fluoro-lH-pyrazole (103 mg, 1.2 mmol) was added and the solution stirred 30 min at the ice-water bath. Into the flask, the solution of ( ?)-3-bromo- N-(2-chloropyridin-4-yl)-2-hydroxy-2-methylpropanamide (293 mg, 1.0 mmol) in 5 mL of anhydrous THF was added through dropping funnel under argon atmosphere at the ice- water bath and stirred overnight at RT. After adding 1 mL of H2O, the reaction mixture was condensed under reduced pressure, and then dispersed into 50 mL of EtOAc, washed with 50 mL (x 2) water, evaporated, dried over anhydrous MgS04, and evaporated to dryness. The mixture was purified with flash column chromatography using as an eluent EtOAc/hexane as a 1:2 ratio to produce compounds to produce the titled compound (55%) as a white solid. (0884) [00408] Compound 1041 was characterized as follows: lH NMR (400 MHz, CDCI3) delta 8.90 (bs, 1H, NH), 8.26 (d, = 5.6 Hz, 1H), 7.63 (s, 1H), 7.75 (d, = 4.2 Hz, 1H), 7.33 (d, = 4.2 Hz, 1H), 7.31 (dd, = 5.6, 1.2 Hz, 1H), 5.88 (s, 1H, OH), 4.53 (d, = 13.6 Hz, 1H), 4.14 (d, = 13.6 Hz, 1H), 1.45 (s, 3H); 19F NMR (CDCI3, decoupled) delta -176.47; MS (ESI) m/z 298.98 [M + H] +; 296.96 [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 35277-02-2, its application will become more common.

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (234 pag.)WO2017/214634; (2017); 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. 288-13-1, name is 1H-Pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 288-13-1

To a solution of copper(I) oxide (0.906 g, 6.33 mmol), salicylaldoximine (3.47 g, 25.3 mmol), 1H-pyrazole (12.93 g, 190 mmol), and cesium carbonate (66.0 g, 203 mmol) in acetonitrile (50.6 ml) under a nitrogen stream was added 3-bromopyridine (20 g, 127 mmol). The reaction mixture was heated at reflux for 24H. The reaction mixture was allowed to cool to ambient temperature, and then diluted with EtOAc, filtered through celite, and washed with H2O and saturated brine solution. The organics were separated, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 0-50% acetone in hexanes to afford 3-(1H-pyrazol-1-yl)pyridine as a yellow oil (17 g, 93%): 1H NMR (400 MHz, acetone-d6) delta 9.14 (d, J=2.2 Hz, 1H), 8.54 (d, J=3.8 Hz, 1H), 8.45 (dd, J=2.5, 0.5 Hz, 1H), 8.24 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 7.79 (d, J=1.5 Hz, 1H), 7.53 (ddd, J=8.3, 4.7, 0.7 Hz, 1H), 6.59 (dd, J=2.5, 1.8 Hz, 1H); EIMS m/z 145.

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 288-13-1.

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35344-95-7, name is 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 35344-95-7, Computed Properties of C4H4N2O

1H-Pyrazole-4-carbaldehyde (6.00 g, 62.44 mmol) was stirred as a suspension in DCM (200 mL). Pyridine (7.58 mL, 93.66 mmol) was added at room temperature and the reaction was stirred for 10 min. 4-Methylbenzenesulfonyl chloride (11.90 g, 62.44 mmol) was added and the reaction was stirred at room temperature for 3 h (Monitored by TLC (KMnO4 visualisation, 100percent EtOAc) which shows new higher running spot and complete conversion after 3 h). The reaction allowed to stand at RT for 16 h. The reaction was diluted with DCM (100 mL) and washed with a saturated aqueous solution of NaHCO3 (100 mL), water (2 x 100 mL), passed through a phase separation cartridge and concentrated under reduced pressure. The resulting residue was purified by flash silica chromatography eluting with 100percent DCM. Product containing fractions were concentrated under reduced pressure to afford 1-(p-tolylsulfonyl)pyrazole-4-carbaldehyde (13.05 g, 84 percent) as a white solid. IR: 1691 (CO), 1373 (SO) , 1180 (SO), cm-1; 1H NMR (400 MHz, CDCl3) 2.45 (s, 3H), 7.38 (d, J = 8.5, 2H), 7.95 (d, J = 8.5, 2H), 8.10 (s, 1H), 8.61 (s, 1H), 9.92 (s, 1H); 13C NMR (400 MHz, CDCl3) 21.80, 125.29, 128.70, 130.35, 134.62, 143.49, 147.03, 183.26.; HRMS [M+H]+ measured 232.0465, C11H10N2O3S requires 232.0461.

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; Watson, David W.; Gill, Matthew; Kemmitt, Paul; Lamont, Scott G.; Popescu, Mihai V.; Simpson, Iain; Tetrahedron Letters; vol. 59; 51; (2018); p. 4479 – 4482;,
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. 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 31230-17-8

4.1.1 N-(3-methyl-1H-pyrazol-5-yl)acetamide (2) 5-methyl-1H-pyrazol-3-amine (1) (10g, 103?mmol) was dissolved in 100?mL of distilled water, NaHCO3 (26g, 309?mmol) was slowly added. Acetic anhydride (19.5?mL, 206?mmol) was then added dropwise and the resulting suspension was heated at reflux for 16?h (monitored by TLC). Then, the mixture was allowed to cool down to RT, white crystals precipitated slowly. The precipitate was collected, washed with water and dried to provide the desired product 2 (6.2g, 44?mmol, 43% yield) without further purification. Mp: 210-211?C; 1H NMR (400?MHz, DMSO-d6) delta 11.92 (s, 1H), 10.19 (s, 1H), 6.24 (s, 1H), 2.17 (s, 3H), 1.96 (s, 3H).

According to the analysis of related databases, 31230-17-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Qiumeng; Shen, Qianqian; Gao, Lixin; Tong, Linjiang; Li, Jia; Chen, Yi; Lu, Wei; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 428 – 441;,
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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H4N2O

To a stirred solution of (l-phenylazetidin-3-yl) methanesuifonate (500 mg, 2.20 mmol) and lH-pyrazole-4- carbaidehyde (317 08 mg, 3.30 mmol) in DMF (10 mL) was added cesium carbonate (1.43 g, 4.40 mmol) anf the reaction mixture was heated to 80 C for 16 hours. After consumption of starting material, the reaction mass was diluted with water, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The crude was purified by combi-flash column chromatography (using 30% ethyl acetate in n-hexane) to afford l-(l-phenyl-azetidin-3-yl)-lH-pyrazole-4-carbaldehyde (300 mg, 1.23 mmol, 55 80% yield, 93% purity, 000) as light yellow solid. LCMS (ES+) = 227 8 | M I f )

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 35344-95-7.

Reference:
Patent; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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. Recommanded Product: 31230-17-8

1.1 -Diniethylethyl 3-amino-5-methyl- lH-pyrazole- 1 -carboxylate; 5-Methyl-lH-pyrazol-3-amine (800 mg, 8.25 mmol) was dissolved in DMF (10 mL) at 0 0C and treated with sodium hydride (336 mg, 8.25 mmol) followed by stirring for a further 30 minutes. Warmed di-tert-butyl dicarbonate (1.80 g, 8.25 mmol) was then slowly added via syringe over 5 min and the reaction was allowed to warm to RT and stirred for a further 1 hour. The reaction was taken up in saturated aqueous sodium hydrogencarbonate (50 mL) and ethyl acetate (100 mL). The organic layer was separated then dried (MgSO4), filtered and evaporated. Purification by column chromatography,eluting with 50-100percent ethyl acetate in isohexane, afforded the title compound as a colourless oil (380 mg). 1R NMR delta (CDCl3): 1.62 (s, 9Eta), 2.43 (s, 3H), 3.87 (s, 2H), 5.60 (s, IH)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 31230-17-8, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/17649; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1453-58-3, 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 1453-58-3 as follows.

Preparation of tert-butyl 3-(bromomethyl)-1H-pyrazole-1-carboxylate After 3-methyl-1-pyrazole (2.0 g, 24.3 mmol) was dissolved in acetonitrile (25 mL), tert-butyl dicarbonate (6.5 g, 29.8 mmol) and 4-dimethylaminopyridine (0.31 g, 2.49 mmol) were added thereto at 0° C., and the mixture was slowly warmed to room temperature and then stirred for 2 hours. Ethyl acetate (50 mL) was added to the reaction material, and the result was washed with a 1N aqueous hydrochloric acid solution (50 mL), a saturated aqueous sodium hydrogen carbonate solution (50 mL) and salted water (50 mL), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (ethyl acetate/normal-hexane=1/4) to give tert-butyl 3-methyl-1H-pyrazole-1-carboxylate (4.13 g, 93percent). 1H-NMR (300 MHz, CDCl3) delta 1.64 (s, 9H), 2.34 (s, 3H), 6.17 (s, 1H), 7.96 (s, 1H).

According to the analysis of related databases, 1453-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; SON, Jong Chan; KIM, Bong Jin; KIM, Jae Hak; LEE, Ill Young; YUN, Chang Soo; LEE, Sang Ho; LEE, Chong Kgo; US2014/249162; (2014); 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 28466-26-4 as follows. category: pyrazoles-derivatives

General procedure: 3 -Phenyl- lH-pyrazol-4-amine (100.0 mg, 0.6 mmol, 1.0 equiv) was dissolved in THF (15.0 mL). TEA (l27. l mg, 1.3 mmol, 2.0 equiv) and l-butyl-4-isocyanatobenzene (132.1 mg, 0.8 mmol, 1.2 equiv) were added dropwise. The solution was then stirred for 2 hours at RT. The resulting solution was concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions: Column: XBridge Prep OBD C18 Column, 30x l50mm 5um; Mobile Phase A:Water (10 MMOL/L NH4HCO3), Mobile Phase B:ACN; Flow rate:60 mL/min; Gradient:50% B to 82% B in 7.5 min; UV 254/210 nm; RTl :4.48. l-(4-Butylphenyl)-3-(3-phenyl-lH-pyrazol-4-yl)urea (30 mg, 14.3%) was isolated as a white solid. LCMS Method G, MS-ESI: 335. l[M+H+]

According to the analysis of related databases, 28466-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IFM DUE, INC.; ROUSH, William R.; VENKATRAMAN, Shankar; GLICK, Gary; SEIDEL, Hans Martin; (171 pag.)WO2020/10155; (2020); 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. 930-36-9, name is 1-Methylpyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

To a stirred solution of 1 -methyl- lH-pyrazole (609 mmol) in dry ether (600 mL) under an atmosphere of nitrogen is added a solution of n-BuLi in hexane (2.6 M, 670 mmol) dropwise at -78C over a period of Ih. The reaction mixture is then stirred at this temperature for a further 1 h, and then dry carbon dioxide gas is passed through the mixture at -78C for 30 min. The reaction mixture is then allowed to warm to room temperature and quenched with water (500 mL). The aqueous phase is separated, washed with ether (500 mL) and cooled to 2-3 0C. To the stirred mixture is added concentrated aqueous hydrochloric acid until a peta of 3 is obtained. The resulting precipitate is collected by filtration, washed with ice-cold water (20 mL), dried first in open air, and then in a vacuum desiccator over P2O5 to afford 2-methyl-2H-pyrazole-3-carboxylic acid as a white powder.[0232] Compound wt: 35.3g, 45.4% yield. 1H NMR (400 MHz, DMSOi6) delta: 13.31 (IH, bs);7.50 (IH, d); 6.81 (IH, d); 4.07 (3H, s).

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; Galapagos NV; WO2009/71706; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics