Pyridine-derivatives

Application of 1594-58-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1594-58-7, name is N-Hydroxynicotinimidamide, molecular formula is C6H7N3O, molecular weight is 137.14, as common compound, the synthetic route is as follows.

3-(3-(pyridin-3-yl)-1 ,2,4-oxadiazol-5-yl)benzonithle 3-Pyridylamideoxime (Aldrich, 5.5 g, 40 mmol) was dissolved in 60 mL of pyridine and 3-cyanobenzoyl chloride (Aldrich, 6.6 g, 40 mmol) was added. The reaction mixture was heated to reflux for 4 hours and then cooled to room temperature. The solution was poured into water (500 mL), filtered, and the solid were collected and dried under vacuum. ^ H NMR (300 MHz, methanol- d4) delta ppm 7.87 (td, J=8.0, 0.7 Hz, 1 H), 8.10 (dt, J=8.1 , 1.4 Hz, 1 H), 8.23 (ddd, J=8.1 , 5.6, 0.8 Hz, 1 H), 8.56 (ddd, J=8.0, 1.7, 1.2 Hz, 1 H), 8.64 (td, J=1 .7, 0.7 Hz, 1 H), 9.04 (dd, J=5.4, 1 .0 Hz, 1 H), 9.23 (dt, J=8.1 , 1 .7 Hz, 1 H), 9.57 (d, J=1.7 Hz, 1 H); MS (+ESI) m/z 249 (M+H)+.

Statistics shows that 1594-58-7 is playing an increasingly important role. we look forward to future research findings about N-Hydroxynicotinimidamide.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/73942; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1086381-28-3, 4-Bromo-2-cyclopropylpyridine, 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, 1086381-28-3, blongs to pyridine-derivatives compound. Quality Control of 4-Bromo-2-cyclopropylpyridine

Example 53i 1-(2-Bromopyridin-4-yl)-1-(2-cyclopropylpyridin-4-yl)-4-fluoro-1H-isoindol-3-amine Under an atmosphere of argon, tert-butyllithium (1.7 M in pentane) (0.576 mL, 0.98 mmol) was added dropwise to anhydrous tetrahydrofuran (4.00 mL) at -100 C. 4-Bromo-2-cyclopropylpyridine (0.097 g, 0.49 mmol) in anhydrous THF (2.00 mL) was added dropwise to the mixture. The solution was stirred for 2 minutes before dropwise addition of a solution of N-((2-bromopyridin-4-yl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide (0.200 g, 0.49 mmol) in anhydrous THF (2.00 mL). The reaction was stirred at -100 C. for 20 minutes, then the temperature was raised to -78 C. over a period of 10 minutes. The reaction was stirred at -78 C. for another 60 minutes. MeOH (2.0 mL) was added dropwise at -78 C. followed by hydrogen chloride (1.25 M in methanol) (1.176 mL, 1.47 mmol). The cooling bath was removed and the reaction was left to stir at ambient temperature for 60 minutes. The solvents were evaporated and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc (*2), the organics were combined, dried (Na2SO4), filtered and evaporated. Purification by silica chromatography using 0 to 5% (3.5 M ammonia in methanol) in dichloromethane gave the title compound (0.094 g, 45%). 1H NMR (500 MHz, DMSO-d6) delta ppm 8.30 (dd, 2H) 7.72 (d, 1H) 7.58 (td, 1H) 7.42-7.47 (m, 1H) 7.37 (dd, 1H) 7.32 (dd, 1H) 7.18-7.22 (m, 1H) 7.00 (dd, 1H) 6.80 (br. s., 2H) 1.99-2.07 (m, 1H) 0.81-0.95 (m, 4H); MS (ES+) m/z 423, 425 [M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1086381-28-3, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2010/125082; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 102368-13-8 ,Some common heterocyclic compound, 102368-13-8, molecular formula is C11H8N2O2S, 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.

A mixture of N-(3-amino-2,4-difluoro-benzyl)-2,2-dimethyl-propionamide (570 mg, 2.35 mmol), 1,1′-thiocarbonyldi-2(1H)-pyridone (550 mg, 2.35 mmol) and dioxane (20 mL) is stirred at reflux overnight. The reaction mixture is concentrated, diluted with DCM, filtered through a pad of silica gel and the filtrate is concentrated to give the title compound.Yield: 440 mg (65%). Rf=0.80 (silica gel, DCM:EtOH 95:5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,102368-13-8, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/149676; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131674-39-0, 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. 131674-39-0, name is 1-(2-Chloropyridin-3-yl)ethanol. A new synthetic method of this compound is introduced below.

Step 2: 1-(2-Chloropyridin-3-yl)ethanone A solution of 1-(2-chloropyridin-3-yl)ethanone (10 g, 0.0635 mol) in dry acetone (200 mL) was introduced under argon into a 1 L flask. The mixture was cooled to -30 C. and pure, pulverized chromic anhydride (19 g, 0.19 mol) was added. The reaction mixture was kept at room temperature for 3 h. 2-Propanol (100 mL) was added, followed by aqueous sodium hydrogen carbonate to pH 8. After filtration, solids were washed with chloroform. The organic and aqueous layers were then separated and the aqueous layer was extracted with chloroform (2*100 mL). The combined organics were dried over anhydrous sodium sulfate and evaporated to yield the crude pyridyl ketone as an oil. This product was purified by column chromatography (8 g, 81%). *1H NMR (CDCl3) 8.44 (dd, J=5 and 2 Hz, 1H) 7.91 (dd, J=7.5 and 2 Hz, 1H), 7.34 (dd, J=7.5 and 5 Hz, 1H), 2.68 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131674-39-0, 1-(2-Chloropyridin-3-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Georg, Gunda I.; Tash, Joseph S.; Chakrasali, Ramappa; Jakkaraj, Sudhakar Rao; US2006/47126; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1001413-01-9, name is 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C13H9F2NO3

The carboxylic derivative 3 (300 mg, 1.13 mmcl) and the amine 2(168 mg, 1.13 mmcl) were combined through a condensation reaction in presence of thecondensing agent TBTU (363 mg, 1.13 mmol). The solvents were evaporated under reduced pressure and the crude product was purified by flash chromatography over silica gel, using 0 – 4% MeOH as a gradient in CHCI3, to obtain pure SST143 as a white solid (210 mg, 0.53 mmol, 47% yield). mp: 285-288 00 1H-NMR (400 MHz, DMSO-d6): 6 3.48 (5, 2H, CH2 indole); 5.28(5, 2H, CH2); 6.68 (dd, 1 H, J= 6.8, 7.2 Hz, Ar); 6.77 (d, 1 H, J= 8.4 Hz, Ar); 7.20-7.23 (m, 1H, Ar); 7.40-7.52 (m, 3H, Ar); 7.66 (5, 1H, Ar); 8.29 (dd, 1H, J= 2.2,6.8 Hz, Ar); 8.46 (dd, 1H, J= 2.2, 6.8 Hz, Ar); 10.33 (5, 1H, NH), 11.87 (5, 1H,NH) ppm. 13C-NMR (101 MHz, DMSO-d6): 6 176.23, 161.54, 160.73, 150.35,147.90, 143.78, 143.42, 139.86, 134.02, 132.32, 126.40, 124.90, 120.35,119.02, 117.74, 117.25, 116.90, 109.10, 107.22, 51.45, 36.02 ppm. 19F-NMR (376 MHz; DMSO-d6): 6-138.17 (d, iF, J= 24 Hz); -139.76 (d, iF, J= 24 Hz) ppm. Anal. Calcd for 021H15F2N303: 0, 63.80%; H, 3.82%; N 10.63%; Found: C, 63.72%; H, 3.55%; N, 10.50%

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, 1001413-01-9, 1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Patent; INTERNATIONAL SOCIETY FOR DRUG DEVELOPMENT S.R.L.; SESTITO, Simona; DANIELE, Simona; MARTINI, Claudia; RAPPOSELLI, Simona; PURICELLI, Guido; (63 pag.)WO2016/198597; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1150617-54-1, name is 6-Bromo-1H-pyrazolo[4,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H4BrN3

A mixture of 6-bromo-1H-pyrazolo[4,3-b]pyridine (0.3 g, 2 mmol;)(Annova Chem Cat. No. L05238), (3,5-dimethoxyphenyl)boronic acid (0.33 g, 1.8 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (100 mg, 0.1 mmol), and potassium phosphate (0.64 g, 3.0 mmol) in 1,4-dioxane (1 mL) and water (0.12 mL) was degassed and sealed. It was stirred at 85 C. overnight. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.38 g). LCMS (M+H)+=256.2.

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, 1150617-54-1, 6-Bromo-1H-pyrazolo[4,3-b]pyridine.

Reference:
Patent; Incyte Corporation; Zhuo, Jincong; Xu, Meizhong; Qian, Ding-Quan; US2014/171405; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 505084-59-3, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.505084-59-3, name is 2-Chloro-5-(trifluoromethyl)nicotinic acid, molecular formula is C7H3ClF3NO2, molecular weight is 225.55, as common compound, the synthetic route is as follows.

To a stirred solution of 478 2-chloro-5-(trifluoromethyl)pyridine-3-carboxylic acid (2 g, 8.87 mmol) in 45 THF (5 mL) and 139 MeOH (5 mL) was added 479 (trimethylsilyl)diazomethane (8.87 mL, 17.73 mmol) (2 M in 123 hexane) dropwise at -20 C. and the reaction was stirred at -20 C. for 2 h. The solvent was concentrated under reduced pressure and the residue was purified by flash silica gel chromatography to afford the 480 title compound as an oil. MS (ESI) m/z: 242.2 [M+H+]

The chemical industry reduces the impact on the environment during synthesis 505084-59-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76469-41-5, 2,3,5-Trifluoropyridine, 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, Product Details of 76469-41-5, blongs to pyridine-derivatives compound. Product Details of 76469-41-5

Example 1 Compound 1 4-(teri-butyldimethylsilyl)-2,3,5-trifluoropyridineA solution of diisopropylamine (98.85 g, 136.9 mL, 976.9 mmol) in THF (1.350 L) was cooled to -65C. n-BuLi (2.5 M in hexanes) (375.8 mL of 2.5 M, 939.4 mmol) was added dropwise via cannula over lh at such a rate as to maintain reaction temperature below -60C. Once the addition was complete the cooling bath was removed and the reaction mixture was allowed to warm up to 0C. The reaction mixture was stirred for 15 min at 0C, then re-cooled to -78C. 2,3,5-trifluoropyridine (100 g, 751.5 mmol) was added dropwise via cannula over 20 min at such a rate to maintain the reaction temperature below -69C. The reaction mixture was stirred for 45 min at -78C during which time the solution turned orange brown. A solution of tert-butyl- chloro-dimethyl-silane (147.2 g, 976.9 mmol) in THF (150 mL) was then added via cannula over 30 min. The reaction mixture was stirred at -78 C for 90 minutes during which time the solution darkened. Lc/Ms after this time indicated that the reaction was complete. A saturated ammonium chloride solution (300ml) was then added and mixture was allowed to warm up to RT. The reaction mixture was diluted with water (100 ml) and extracted with EtOAc (1.5L then 2 x 500ml). The combined organics were washed with saturated NaHCO (500ml) and brine (400 ml). The crude mixture was partially concentrated in vacuo, dried over magnesium sulfate, filtered and concentrated in vacuo to an oil. The crude was purified by flash chromatography (CombiFlash Companion XL, 1.5kg column, 0-20% ethyl acetate in petroleum ether). This afforded the title compound as a colourless oil (136.2 g, 73%); XH NMR (CDC13) 0.34 (6H, s), 0.89 (9H, s), 7.73 (1H, s); MS ES(+) 248.25 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76469-41-5, 2,3,5-Trifluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; JIMENEZ, Juan-Miguel; GOLEC, Julian, M.C.; SETTIMO, Luca; FRAYSSE, Damien; BRENCHLEY, Guy; BOYALL, Dean; TWIN, Heather; YOUNG, Stephen; MILLER, Andrew, W.; DAVIS, Christopher, John; WO2011/94283; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13600-49-2 ,Some common heterocyclic compound, 13600-49-2, molecular formula is C8H5F3N2, 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.

A. tert-Butyl ((6-Methyl-4-(trifluoromethyl)pyridin-3-yl)methyl)carbamate 6-Methyl-4-(trifluoromethyl)nicotinonitrile (1.0 equiv.) was dissolved in MeOH (0.1 M), wet Raney nickel was added, followed by ammonium hydroxide (32 equiv.). The reaction vessel was evacuated three times, refilled with hydrogen and then equipped with a hydrogen balloon and stirred at room temperature for 48 h. The mixture was filtered through a short pad of celite which was washed with MeOH. Ethanol was added to remove excess water upon concentration. The volatile solvents were removed to afford crude product which was dissolved in DCM. DIEA (1.8 equiv.) was added followed by BOC2O (0.95 equiv.). The reaction was stirred at room temperature for 1 h. The volatile solvent was removed and the residue was purified via Biotage chromatography (10-100% ethyl acetate in hexanes) to afford tert-butyl ((6-methyl-4-(trifluoromethyl)pyridin-3-yl)methyl)carbamate (90% yield); MS(ESI) m/z 290.3 [M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13600-49-2, its application will become more common.

Reference:
Patent; Papa, Patrick; Cathers, Brian Edwin; CALABRESE, Andrew Antony; WHITEFIELD, Brandon Wade; BENNETT, Brydon; CASHION, Daniel; MORTENSEN, Deborah; HUANG, Dehua; TORRES, Eduardo; PARNES, Jason; SAPIENZA, John; HANSEN, Joshua; LEFTHERIS, Katerina; CORREA, Matthew; DELGADO, Maria Mercedes; RAHEJA, Neil; BAHMANYAR, Sami; HEGDE, Sayee; NORRIS, Stephen; PLANTEVIN-KRENITSKY, Veronique; US2015/175557; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 871826-12-9, (5-(Trifluoromethyl)pyridin-2-yl)methanamine hydrochloride, 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, 871826-12-9, blongs to pyridine-derivatives compound. name: (5-(Trifluoromethyl)pyridin-2-yl)methanamine hydrochloride

General procedure: The carboxylic acid 8 is dissolved in DMF and 2 eq. of the corresponding amine component, 1.5 eq. of HATU and 3 eq. of triethylamine are added. The reaction mixture is stirred at rt until TLC and/or LCMS indicate complete consumption of the starting material (2 h), then water is added. The formed precipitate is filtered off, washed with water and dried in a vacuum drying cabinet at 40C. If appropriate, the product is purified by preparative HPLC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,871826-12-9, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; PANKNIN, Olaf; BAeURLE, Stefan; RING, Sven; SCHWEDE, Wolfgang; BONE, Wilhelm; NOWAK-REPPEL, Katrin; BENDER, Eckhard; NUBBEMEYER, Reinhard; GNOTH, Mark, Jean; WO2013/107743; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem