Category: pyridine-derivatives

Application of 15506-18-0, 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.15506-18-0, name is 1-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, molecular formula is C7H7NO3, molecular weight is 153.1354, as common compound, the synthetic route is as follows.

b) 3-({9-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9- diazaspiro[5.5]undec-3-yl}carbonyl)-1-methylpyridin-2(lH)-oneN-methyl-2-hydroxynicotinic acid (45 mg, 0.29 mmol), Intermediate A (76 mg, 0.24 mmol), HATU (91.9 mg, 0.24 mmol) and triethylamine (43 mg, 0.43 mmol) in CH2Cl2 (4 mL) were mixed and stirred for Ih. The reaction mixture was diluted with saturated aqueous sodium carbonate (2 mL) and the product was extracted with dichloromethane and dried. The pure title compound was obtained by preparative HPLC.1H NMR (399.99 MHz, CD3OD) delta 7.81-7.71 (m, IH), 7.60-7.52 (m, IH), 7.32-7.26 (m, IH), 7.23-7.16 (m, IH), 6.97-6.88 (m, IH), 6.48-6.36 (m, IH), 4.32-4.19 (m, 2H), 3.79- 3.67 (m, 2H), 3.62-3.55 (m, 3H), 3.45-3.35 (m, 2H), 3.26-3.06 (m, 4H), 2.08-1.96 (m, 2H), 1.84-1.37 (m, 14H)APCI-MS m/z: 450.5 [MH+]HPLC (Method A) Retention time: 5.63 minHPLC (Method B) Retention time: 7.07 min

The chemical industry reduces the impact on the environment during synthesis 15506-18-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2007/30061; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 10128-91-3 ,Some common heterocyclic compound, 10128-91-3, molecular formula is C7H7NO3, 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: 2-Hydroxynicotinic acid methyl ester (CAS number 10128-91-3) (100-200 mg scale), the corresponding aryl iodide (0.95 equiv), CuBr (10 mol%), 2-ethylester cyclohexanone (20 mol%) and Cs2CO3 (2.2 equiv) were suspended in DMSO (anhydrous, 2-3 mL) in a sealed tube. The reaction was complete after about 18 h heating at 60 C. The mixture was diluted in EtOAc and washed with brine. The aqueous phase was re-extracted once with EtOAc. The combined organic phases were dried over anhydrous MgSO4, and the solids filtered off. The solvent was removed in vacuo and the resulting crude material purified by column chromatography over lica gel, EtOH/CH2Cl2. The products were isolated in good yields (53-58%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10128-91-3, its application will become more common.

Reference:
Article; Suarez, Rosa M.; Chevot, Franciane; Cavagnino, Andrea; Saettel, Nicolas; Radvanyi, Francois; Piguel, Sandrine; Bernard-Pierrot, Isabelle; Stoven, Veronique; Legraverend, Michel; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 2 – 25;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 126325-47-1 ,Some common heterocyclic compound, 126325-47-1, molecular formula is C6H7BrN2, 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.

Preparation VI; 6-Cyano-2-methyl-3-aminopyridine; A mixture of 3.5 g (18.6 mmol) of 6-bromo-2-methyl-3-aminopyridine, 352 mg (0.37 mmol) of tris(benzylideneacetone)dipalladium(0), 532 mg (0.92 mmol) of 1,1′-bis(diphenylphosphino)ferrocene, 146 mg (2.2 mmol) of zinc powder and 1.4 g (12 mmol) of zinc cyanide in 70 ml of N,N-dimethylacetamide is prepared and the reaction mixture is then stirred at 20 C. for 22 hours. It is diluted with 200 ml of ethyl acetate and washed with 2 N ammonium chloride solution. (Decantation is obtained only after filtration of the mixture on a filter aid of the Celite type.) The organic phase obtained is washed with sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (9/1; v/v) as the eluent to give 1.6 g of the expected compound in the form of a yellow powder (yield=65%). M.p.=192-196 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,126325-47-1, its application will become more common.

Reference:
Patent; Laboratoires Fournier S.A.; US2007/54955; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 16867-03-1, name is 2-Amino-3-hydroxypyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

15.6 g (141.6 mmol) of 2-amino-3-hydroxypyridine are initially charged in 300 ml of glacial acetic acid, 15.6 g (141.6 mmol) of 2-amino-3-hydroxypyridine are initially charged in 300 ml of glacial acetic acid, [0294] 5.1 g of 5% rhodium/ carbon catalyst are added and the mixture is hydrogenated in a 600 ml vessel (material: Hastelloy) at room temperature (20 C.) at 4.5 bar for about 16 hours. The entire reaction mixture is then filtered (removal of the catalyst) and concentrated under reduced pressure, and the residue that remains is recrystallized from an ethanol/ether mixture. This gives 5.9 g (23.9% of theory) of a (2:1) mixture of 2-amino-3-hydroxypyridine and 2-amino-3,4,5,6-tetrahydropyridin-2-ol acetate CH NMR spectrum: some Py-H) which can be used for the next reaction. [0295] 1H NMR (600 MHz, D2O) delta 1.79 (br., m, 1H), 1.90-1.92 (m, 1H), 1.99-2.00 (br., m, 1H), 2.22 (br., m, 1H), 3.37 (m, 2H), 4.52 (m, 1H), 6.77-6.78 (m, 1H), 7.18-7.19 (m, 1H), 7.28-7.29 (m, 1H) ppm; At room temperature, 1.0 g (5.74 mmol) of the (2:1) mixture of 2-amino-3-hydroxypyridine and 2-amino-3,4,5,6-tetrahydropyridin-2-ol acetate (cf. step 1) are stirred with 1.26 g (7.79 mmol) of 1,1?-carbonyldiimidazole (CDI), 39.9 mg of 4-dimethylaminipyridine (DMAP) in 6 ml of dichloromethane, and 1.2 ml of triethylamine are added. The entire reaction mixture is then stirred at room temperature for another about 24 hours. The reaction mixture is then concentrated under reduced pressure, the residue that remains is taken up in ethyl acetate and the organic phase is washed with water. The organic phase is separated off and then dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue that remains is purified chromatographically by medium-pressure chromatography (cyclohexane/acetone gradient). This gives 753.0 mg (93.2% of theory) of a mixture of oxazolo[4,5-b]-5,6,7,7a-tetrahydropyridin-2(4H)-one [0301] and oxazolo[4,5-b]pyridin-2(3H)-one (cf. WO 2010/135014 A1) (1H NMR spectrum: some Py-H and LC-MS m/z: 137.0) which can be used for the next reaction. [0302] LC-MS (ESI positive): m/z found: 141.0 [M++H]. [0303] C6H8N2O2 calculated: 140.0.

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, 16867-03-1, 2-Amino-3-hydroxypyridine.

Reference:
Patent; Jeschke, Peter; Schindler, Michael; Woelfel, Katharina; Ebbinghaus-Kintscher, Ulrich; Voerste, Arnd; Malsam, Olga; Losel, Peter; Goergens, Ulrich; US2014/113824; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2002-04-2, 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.2002-04-2, name is 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine, molecular formula is C7H6N4S, molecular weight is 178.21, as common compound, the synthetic route is as follows.

General procedure: An equimolar amount of 5-(pyridin-4-yl)-1,3,4-thiadiazol-2-amine (3c) dissolve in 10-15mL of tetrahydrofuran (THF), add 2-3 drops of triethylamine, to this solution add 1.5mol different aryl chlorides gradually, continuous stirring for 3h on ice bath(0C). After completion of reaction solid will precipitate out, washed with sodium bicarbonate solution to remove excess of chloride and recrystallized from ethanol to get pure compound.

The chemical industry reduces the impact on the environment during synthesis 2002-04-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Patel, Harun; Jadhav, Harsha; Ansari, Iqrar; Pawara, Rahul; Surana, Sanjay; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 1 – 9;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 18653-75-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 18653-75-3, name is 2-(1H-Imidazol-2-yl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a mixture of 1.45 g (10 mmol) of 2-pyridyl-1H-imidazole, 0.62 g (11 mmol) of powdered KOH, and 10 mL of ethylene glycol dimethyl ether was added dropwise 0.68 g (11 mmol) of methyl iodide with vigorous stirring at 3-5 C, maintaining the reaction temperature no higher than 8 C. The mixture was stirred at this temperature for 0.5 h, and then poured into 100 mL of water. The reaction product was filtered off or extracted with chloroform (2×50 mL). The extract was dried over calcium chloride, chloroform was distilled off. The residue was extracted with hot hexane (3×50 mL) and evaporated to give the corresponding 1-methyl-2-pyridyl-1H-imidazole.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 18653-75-3, 2-(1H-Imidazol-2-yl)pyridine.

Reference:
Article; El?chaninov; Aleksandrov; Klushin; Russian Journal of General Chemistry; vol. 86; 7; (2016); p. 1581 – 1583; Zh. Obshch. Khim.; vol. 86; 7; (2016); p. 1102 – 1105,3;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.126325-47-1, name is 6-Bromo-2-methylpyridin-3-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.Product Details of 126325-47-1

Into a 50-mL seal tube was placed methyl 6-bromo-2-methylpyridin-3 -amine (500 mg, 2.67 mmol) in MeOH (15 mL) and Pd(OAc)2(120 mg, 0.53 mmol), dppf (444 mg, 0.80 mmol), TEA (809 mg, 8.01 mmol). The seal tube was evacuated and flushed three times with CO. The resulting solution was stirred for 5 h at 100C under 10 atm of CO. Then the solution was concentrated under vacuum. The residue was eluted from a silica gel column with ethyl acetate/petroleum ether (1 : 1).This resulted in 351 mg (79.2 %) of the title compound as a light yellow solid. MS-ESI: 167 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,126325-47-1, 6-Bromo-2-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); 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. 6959-47-3, name is 2-(Chloromethyl)pyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. name: 2-(Chloromethyl)pyridine hydrochloride

Synthesis of [N,N?-Dimethyl-N,N?-bis-(pyridine-2-ylmethyl)-1,2-diaminoethane] was taken from a previously reported procedure [16]. 2-(chloromethyl)pyridine hydrochloride (1.501 g, 9.15 mmol) dissolved in 5 mL deionized (DI) water was added dropwise to an aqueous solution containing K2CO3 (2.556 g, 18.49 mmol) dissolved in 7.5 mL DI water. The resulting mixture was stirred for 30 min. The mixture was extracted with CH2Cl2 (3×10 mL). The organic phase was collected and dried with anhydrous Na2SO4. The dried solution was concentrated in vacuo to afford orange oil. A solution containing N,N?-dimethylethylenediamine (0.471 mL, 4.38 mmol) in 15 mL CH2Cl2 was added dropwise to the aforementioned orange oil dissolved in 5 mL CH2Cl2. An aqueous solution containing NaOH (0.311 g, 7.78 mmol) dissolved in 7.6 mL DI water was slowly added to organic mixture and stirred at room temperature. After 60 h, a second portion of NaOH solution(0.318 g, 7.95 mmol) was quickly added to the mixture. The combined mixture was extracted with CH2Cl2 (3×20 mL) and dried with anhydrous Na2SO4. The organic solution was concentrated in vacuo to afford a brown oil, BPMEN (Yield: 0.631 g, 2.33 mmol, 70%) 1H NMR(500 MHz, CD2Cl2) delta 8.46 (dt, 2H, pyridine ring), 7.80 (m, 2H, pyridinering), 7.51 (m, 2H, pyridine ring), 7.30 (m, 2H, pyridine ring), 3.70 (m,4H, -CH2), 2.66 (m, 4H, -CH2), 2.27 (s, 6H, -CH3). ESI-MS (MeOH).Observed m/z 271.25 [BPMEN+H+] (z=1); simulated m/z 271.19.

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, 6959-47-3, 2-(Chloromethyl)pyridine hydrochloride.

Reference:
Article; Pella, Bruce J.; Niklas, Jens; Poluektov, Oleg G.; Mukherjee, Anusree; Inorganica Chimica Acta; vol. 483; (2018); p. 71 – 78;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 124433-70-1, Adding some certain compound to certain chemical reactions, such as: 124433-70-1, name is 6-Fluoropyridine-2-sulfonamide,molecular formula is C5H5FN2O2S, 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 124433-70-1.

To 6-phenyl-2-(2,4,6-trimethylphenoxy)pyridine-3-carboxylic acid (150 mg, 0.450 mmol), HATU (171 mg, 0.450 mmol), DMF (1.5 mL), and triethylamine (137 mg, 188 muL, 1.35 mmol) was added 6-fluoropyridine-2-sulfonamide (79.3 mg, 0.450 mmol) was added and the reaction mixture was allowed to stir at 65 C. for 1 h. The reaction mixture was filtered and purified via HPLC (1%-99%) ACN:H2O with a 0.1% HCl modifier to give N-[(6-fluoro-2-pyridyl)sulfonyl]-6-phenyl-2-(2,4,6-trimethylphenoxy)pyridine-3-carboxamide (Compound 698) (79 mg, 36%) 1H NMR (400 MHz, DMSO-d6) delta 8.37 (q, J=7.8 Hz, 1H), 8.16 (dd, J=7.5, 2.1 Hz, 1H), 8.12 (d, J=7.8 Hz, 1H), 7.80-7.73 (m, 3H), 7.59 (dd, J=8.3, 2.2 Hz, 1H), 7.41 (ddt, J=5.5, 3.8, 2.2 Hz, 3H), 6.94 (s, 2H), 2.28 (s, 3H), 2.01 (s, 6H). ESI-MS m/z calc. 491.1315. found 492.4 (M+1)+. Retention time: 2.19 minutes.

According to the analysis of related databases, 124433-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19337-97-4, 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.19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid, molecular formula is C8H7NO2, molecular weight is 149.15, as common compound, the synthetic route is as follows.

Synthesis of 3-(3-pyridinyl)propanoic acid beta-(3-Pyridyl)-acrylic acid (10 g) is placed in a Parr hydrogenation bottle with 150 ml of glacial acetic acid, 100 ml of absolute ethanol and a large scoop of palladium on carbon catalyst. The solution is shaken at 50 psi of hydrogen and re-pressurized as needed until hydrogen uptake ceases (approximately 3 hours). The solution is filtered through celite, washed with ethanol and the solvent is evaporated in vacuo and azeotroped with toluene to yield the desired product as white crystals.

Statistics shows that 19337-97-4 is playing an increasingly important role. we look forward to future research findings about trans-3-(3-Pyridyl)acrylic acid.

Reference:
Patent; Procter & Gamble Pharmaceuticals, Inc.; US5391743; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem