Category: pyridine-derivatives

Reference of 1206102-07-9, 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. 1206102-07-9, name is Methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate. A new synthetic method of this compound is introduced below.

A reactor was charged with (3.759 kg, 11.27 mol) of methyl 1-(2,3-dihydroxypropyl)-4-oxo- 3-[(phenylmethyl)oxy]-1 ,4-dihydro-2-pyridinecarboxylate 7 and 18.8 L of DMF. To this agitated mixture at 18-20 0C was added N-bromosuccinimide (2.220 kg, 12.47 mol) over 20 minutes via a powder funnel. The resultant mixture was stirred at rt for 16 h. At this time less than 1% of starting material was present by HPLC. The mixture was worked up in half batches by cooling to 10 0C and added an ice/water mixture (12 kg ice in 35 kg deionized water) and the mixture was agitated, then filtered. This was repeated for the second half of the batch. The combined filter cake was washed with 14 L of water and dired in a vaccum oven to provide 4.033 kg of methyl 5-bromo-1-(2,3-dihydroxypropyl)-4- oxo-3-[(phenylmethyl)oxy]-1 ,4-dihydro-2-pyridinecarboxylate 19 (91.6%) as an off-white powder of 99.2% HPLC purity. 1H NMR(300 MHz, Methanol-d4) delta 8.21 (s, 1 H), 7.41-7.33 (m, 5 H), 5.16 (s, 2 H), 4.17 (dd, J = 14.3, 2.4 Hz, 1 H), 3.90 (dd, J = 14.3, 9.0 Hz, 1 H), 3.81 (s, 3 H), 3.78 (m, 1 ), 3.52 (dd, J = 11.3, 4.8 Hz, 1 H), 3.41 (dd, J = 11.3, 6.3 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206102-07-9, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; SHIONOGI & CO., LTD.; JOHNS, Brian, Alvin; DUAN, Maosheng; HAKOGI, Toshikazu; WO2010/68262; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 2459-09-8, 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.2459-09-8, name is Methyl isonicotinate, molecular formula is C7H7NO2, molecular weight is 137.136, as common compound, the synthetic route is as follows.

Step 1. Synthesis of methyl 2-(hydroxymethyl)isonicotinate (59):A solution of methyl isonicotinate (58; 70 grams 0.5 mol), ammonium peroxodisulfate (233 grams, 1.02 mol), and cone, sulfuric acid (5 mL) in methanol (600 mL) was refluxed until starting material was consumed. The reaction was concentrated, water was added and the solution was neutralized to pH=9 with K2CO3. The resulting aqueous solution was extracted with ethyl acetate, and the extracts were concentrated, stirred with petroleum ether for 1 hour and the solids were collected by filtration to obtain 15 grams (18% yield) of 2- (hydroxymethyl)isonicotinate 59.

Statistics shows that 2459-09-8 is playing an increasingly important role. we look forward to future research findings about Methyl isonicotinate.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; NARAYAN, Radha; DISCH, Jeremy, S.; PERNI, Robert, B.; VU, Chi, B.; WO2010/56549; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 72990-37-5 ,Some common heterocyclic compound, 72990-37-5, molecular formula is C6H4ClNO, 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.

Magnesium (86.5 mg, 3.60 mmol) was stirred vigorously under nitrogen for 30 min. THF (2 mL) and dibromoethane (2 drops) were added and the reaction mixture was warmed to 50 C. A solution of 4-bromotetrahydropyran (495 mg, 3.00 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 2 h. A solution of 3-chloro-4-pyridaldehyde (170 mg, 1.20 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 6 h, stirred at room temperature overnight and heated at reflux for 8 h. The reaction mixture was cooled to 0 C. and quenched with sat aq NH4Cl (10 mL). The reaction mixture was diluted with EtOAc (40 mL) and the aqueous fraction was extracted with EtOAc (3*40 mL). The combined organic fractions were washed with sat aq Na2CO3 (20 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography to give the crude title compound as a pale yellow gum (69.0 mg, 25%). LCMS (ES+): 228.2 (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,72990-37-5, its application will become more common.

Reference:
Patent; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2013/102587; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6937-03-7, 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.6937-03-7, name is Methyl 2-aminoisonicotinate, molecular formula is C7H8N2O2, molecular weight is 152.1506, as common compound, the synthetic route is as follows.

Methyl 2-aminopyridine-4-carboxylate (2 g, 13.14 mmo 1, 1.00 equiv) wasdissolved in tert-butano 1 (20 mL) after which di-tert-butyl dicarbonate (4.02 g, 18.42mmol, 1.40 equiv) was added. The reaction mixture was agitated at 60C overnight then the reaction was halted through the addition of an aqueous 1M NaHCO3 solution (50 mL). The solid was recovered by filtration, washed with 50 mL of EtOH then dried in vacuo to yield 2.5 g (75 %) of compound 2E in the form of a white solid.

Statistics shows that 6937-03-7 is playing an increasingly important role. we look forward to future research findings about Methyl 2-aminoisonicotinate.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 462-08-8, 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 462-08-8, name is Pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of pyridin-3-ylamine (20 g, 212.49 mmol, CAS RN 462-08-8) in a mixture of THF:Et2O (175 mL; 2.5:1 v/v) was added slowly a solution of pivaloyl chloride (26 mL, 212.5 mmol, CAS RN 3282-30-2) in THF (50 mL) and Et3N (44 mL, 318.7 mmol) at 0 C. and left stirring at that temperature for 1 h. After the completion of reaction, the reaction mixture was filtered, and the filtrate was evaporated in vacuo. The crude filter cake was washed with n-hexane to yield the title compound. Colorless crystalline solid (32 g, 85%). MS (ESI): m/z=179.4 [M+H]+.

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 462-08-8, Pyridin-3-amine.

Reference:
Patent; Bissantz, Caterina; Dehmlow, Henrietta; Erickson, Shawn David; Karnachi, Prabha Saba; Kim, Kyungjin; Martin, Rainer E.; Mattei, Patrizio; Sander, Ulrike Obst; Pietranico-Cole, Sherrie Lynn; Richter, Hans; Ullmer, Christoph; US2012/232051; (2012); A1;,
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.103041-38-9, name is Ethyl 3-(pyridin-2-ylamino)propanoate, molecular formula is C10H14N2O2, molecular weight is 194.23, as common compound, the synthetic route is as follows.COA of Formula: C10H14N2O2

The embodiment of the 6 products obtained 10g, adding tetrahydrofuran 100 ml dissolved, adding 3.2gDBU, 4 . 5g3 – (pyridin-2-yl amino) propionic acid ethyl ester, the temperature is increased to 50 C reaction 7 hours, TLC (developing solvent: ethyl acetate: petroleum ether = 4:1) determine the end point of the reaction. After the completion of reaction, concentrating under reduced pressure to dry. Residue using ethyl acetate 150 ml dissolved, water 100 ml washing secondary, after drying with anhydrous sodium sulfate concentrated under reduced pressure to dry. Residue plus isopropanol refining to obtain a target compound product, yield 82.6%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103041-38-9, Ethyl 3-(pyridin-2-ylamino)propanoate, and friends who are interested can also refer to it.

Reference:
Patent; Chongqing Institute of Pharmaceutical Industry Co., Ltd.; Xing, Naiguo; Wang, Li; Cai, Pengfei; Zheng, Deping; (14 pag.)CN105523999; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1003-68-5 ,Some common heterocyclic compound, 1003-68-5, molecular formula is C6H7NO, 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.

Aromatic heterocyclic substrates 1s (0.1mmol), 5-methylpyridone 2b (0.15mmol), copper acetate hydrate (0.1mmol), potassium acetate (0.2mmol), DMSO (1.0mL) respectively in an air atmosphere Add to a 15mL Schlenk tube, and then directly seal the tube at 80 C for 12h. After the reaction was completed, the mixture was cooled to room temperature, and a small amount of ethyl acetate and ammonia were added to quench the reaction. The ethyl acetate was repeatedly extracted. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered under reduced pressure, and the solvent was evaporated under reduced pressure. The crude product was separated and purified by a preparative plate (DCM: MeOH = 35: 1) to obtain 3sb as a white solid, 23.2 mg, with a yield of 60%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-68-5, its application will become more common.

Reference:
Patent; Shanghai Laishi Blood Goods Co., Ltd.; Wang Peng; Yu Jinfeng; Li Jianjun; (32 pag.)CN110386929; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 55758-32-2, Adding some certain compound to certain chemical reactions, such as: 55758-32-2, name is 6-Fluoropyridin-3-ol,molecular formula is C5H4FNO, 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 55758-32-2.

Step 2: To a solution of 6-fluoropyridin-3-ol (75 g, 663 mmol) in DMF (265 mL, 663 mmol) were added potassium carbonate (59.7 g, 995 mmol) and iodomethane (108 g, 763 mmol). The resulting slurry was heated at 100 C for 3 hours. The reaction was diluted with water (1000 mL) and poured into a separatory funnel containing diethyl ether (1000 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (4 x 500 mL). The combined organic layers were washed with water and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide a yellow oil. This oil was diluted with 500 mL of DCM and concentrated to provide a yellow oil with a large amount of an off white precipitate. The mixture was filtered and the derived solid was washed well with DCM. The filtrate was concentrate to provide a mixture consisting of a yellow oil and an off white solid. The solid was filtered, washing with DCM. Repeat this procedure again and then concentrated the filtrate to provide a yellow oil. The oil was taken up in 100 mL of ether and flashed through a plug of silica gel with 10:1 hexanes:ether to provide 2-fluoro-5-methoxypyridine as a yellow oil.

According to the analysis of related databases, 55758-32-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; EPSTEIN, Oleg; WHITE, Ryan; WEISS, Matthew; ZHONG, Wenge; LOW, Jonathan; WO2012/71279; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 24016-03-3, 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 24016-03-3, name is 2-Amino-3-benzyloxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 1A Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate 25 g (124.8 mmol) of 2-amino-3-benzyloxypyridine were dissolved in 781 ml of ethanol, 102.7 g (624.2 mmol) of ethyl 2-chloroacetoacetate and two tablespoons of 4 A molecular sieve were added, and the reaction mixture was then heated at reflux (bath temperature 100 C.) for 2 days. The mixture was concentrated, and excess ethyl 2-chloroacetoacetate was removed on a rotary evaporator with dry ice cooling. The residue was purified by silica gel chromatography (mobile phase cyclohexane:ethyl acetate gradient 9:1, 4:1). This gave 20.81 g of the target compound (54% of theory, purity 99%). LC-MS (Method 2): Rt=1.12 min MS (ESpos): m/z=311 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=1.35 (t, 3H), 2.59 (s, 3H), 4.34 (q, 2H), 5.32 (s, 2H), 7.01-7.09 (m, 2H), 7.33-7.48 (m, 3H), 7.52 (d, 2H), 8.81-8.86 (m, 1H).

According to the analysis of related databases, 24016-03-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55934-00-4, 3,4-Dichloropyridine, 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, 55934-00-4, blongs to pyridine-derivatives compound. category: pyridine-derivatives

As described previously by Marzi, E. et al. (Eur. J. Org. Chem. 2001, 1371-1376), 2,2,6,6-tetramethylpiperidine (8.84 mL, 52 mmol, Aldrich) in 50 mL of ether at 0 C. was charged with n-BuLi (33 mL, 52 mmol, Aldrich, 1.6 M hexanes). After stirring at 0 C. for 30 min, the solution was cooled to -78 C. and charged with a solution of 3,4-dichloropyridine (7.0 g, 47 mmol, Matrix) in 5 mL of ether. After stirring at -78 C. for 2 h, carbon dioxide (dry ice) was bubbled into the reaction mixture via cannula at which time the solution became heterogeneous. After bubbling carbon dioxide into the reaction at -78 C. for 10 min, the cooling bath was removed and the reaction mixture was allowed to warm to rt with CO2 bubbling. The reaction was quenched with saturated aqueous ammonium chloride solution (50 mL) and stirred at rt under an atmosphere of air for 5 min. The reaction mixture was diluted with water (150 mL) and extracted with ethyl acetate (2¡Á75 mL) to remove any remaining starting material. The aqueous layer was acidified to pH 1-2 with 1N aqueous HCl solution and extracted with ethyl acetate (2¡Á100 mL). The organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo to give 3,4-dichloropicolinic acid (3.5 g, 39%) as a yellow solid. 1H NMR (DMSO-d6) delta 8.53 (d, 1H, J=5.2 Hz), 7.90 (d, 1H, J=5.2 Hz); MS (ESI+) m/z 192.08 (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,55934-00-4, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/114033; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem