Pyridine-derivatives

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.73781-91-6, name is Methyl 6-chloronicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.COA of Formula: C7H6ClNO2

Example 7. Preparation of 0-(6-pyrazol-l-yl-pyridin-3-almethel)-hadroxylamine (Compound of formula (Xl)); Step 7a. Preparation of 6-Pyrazol-1-vl-nicotinic acid methyl ester (Compound of formula (XI-a)); To a solution of pyrazole (19.4g, 0. 28mol) in 100 mL anhydrous DMSO, which was at a temperature of 0C, was added NaH (7. 5g, 0. 3mol) gradually over a period of 30 min. The resulting reaction mixture was allowed to warm to room temperature, at which the mixture continued to agitate for an additional 30 min. Methyl 6- chloronicotinate (35g, 0. 2mol) was added to the stirring reaction mixture and agitated vigorously for a period of 6 hr. The reaction mixture was subsequently cooled to a temperature of about 0C and poured into a saturated aqueous, 0C NH4C1 solution. The resulting precipitate was filtered, washed with water, and dried to give a compound of formula (XI-a) (38.3g, 93% yield) as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73781-91-6, Methyl 6-chloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WO2005/70918; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1539-42-0, Bis(pyridin-2-ylmethyl)amine, 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 1539-42-0, blongs to pyridine-derivatives compound. Product Details of 1539-42-0

N-(2-pyridylmethyl)amine 0.5 mL, N-(2-bromoethyl)phthalimide 0.75g it was heated to 5 mL at 95 C with 0.5 g of potassium carbonate. After cooling to room temperature, the reaction mixture was poured into ice water for 2 hr. The crude product was filtered off and washed with cold water and dried with calcium chloride under vacuum. A yellow brown solid 680 mg was obtained in a yield of 65.7%.

The synthetic route of 1539-42-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen University; Lin Jing; Ma Gongcheng; Zeng Leli; Huang Peng; (24 pag.)CN109020955; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5969-83-5, 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 5969-83-5, name is 2-(4-Chlorophenyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a typical reaction, a 10 mL oven-dried reaction vessel was charged with Pd/MgLa mixed oxide (30 mg), 2-phenylpyridine (29 mg, 0.2 mmol), benzyl alcohol (108 mg, 1 mmol), tert-butyl hydroperoxide (70% solution in water, ?129 mg, 1 mmol) and chlorobenzene (0.5 mL) were added. The resulting solution was stirred at 120 C for 8 h in open air. The reaction was monitored by thin-layer chromatography (TLC). After cooling to room temperature, catalyst was separated by simple centrifugation. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography using silica gel and a mixture of hexane/ethyl acetate as eluents. All the products were confirmed by 1H NMR and 13C NMR spectroscopy. The recovered catalyst was used for the next cycle without any further purification.

According to the analysis of related databases, 5969-83-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kishore; Kantam, M. Lakshmi; Yadav; Sudhakar; Laha; Venugopal; Journal of Molecular Catalysis A: Chemical; vol. 379; (2013); p. 213 – 218;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 62774-90-7, 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.62774-90-7, name is 2,6-Dichloro-4-methylnicotinic acid, molecular formula is C7H5Cl2NO2, molecular weight is 206.03, as common compound, the synthetic route is as follows.

a) Synthesis of 6-chloro-2-ethylsulfanyl-4-methyl-pyridine-3-carboxylic acid 6.1 g (153 mmol, 60% w/w in mineral oil) NaH were dissolved in THF (90 ml) at 0 C. At this temperature 3.4 g (54.7 mmol) ethane thiol were added. After stirring for 15 min at 0 C., 12.4 g (60.2 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid were added portionwise. The RM was allowed to warm to RT and stirring was continued at RT for 16 h. Then the reaction was quenched with a 2M aq. HCl and diluted with EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Crystallisation (DCM/hexane) of the residue yielded 12.0 g (51.7 mmol, 95%) 6-chloro-2-ethylsulfanyl-4-methyl-pyridine-3-carboxylic acid.

The chemical industry reduces the impact on the environment during synthesis 62774-90-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Grunenthal GmbH; US2012/101079; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 132308-19-1, 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 132308-19-1, name is Methyl 5-chloropyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To the reaction flask was added 1 mmol of compound F5,N, N-dimethylglycine,Copper iodide,Cs2CO3,1,4-dioxane and2 mmol of methyl 5-chloropyridine-2-carboxylate,Nitrogen under the protection of heating to 80 C reaction 24h,After the reaction was complete,Extracted with ethyl acetate,The organic phases were combined and dried over anhydrous sodium sulfate; after concentration under pressure,And then purified on a silica gel column (eluent petroleum ether: ethyl acetate = 1: 1)To give the object product as a pale yellow oily liquid.

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 132308-19-1, Methyl 5-chloropyridine-2-carboxylate.

Reference:
Patent; Guangdong Zhongsheng Pharmaceutical Co., Ltd.; Chen, Lijuan; Long, Chaofeng; Chen, Xiaoxin; Liu, Zhuowei; Ye, Haoyu; Xie, Chengshi; (104 pag.)CN106045923; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 133081-24-0 ,Some common heterocyclic compound, 133081-24-0, molecular formula is C6H7N3O2, 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.

6-chloronicotinic acid (1.6 g ) in MeOH (1OmL) was treated with NH2NH2 (2 g) at 140 0C for 2h. After cooling to -20 0C, the solid was filtered to give 560mg of compound 33B. Compound 33B was treated with isothiocyanatobenzene (141 mg) in 1 ,2-dichlorobenzene (5 mL) at 100 0C for 10 min, and then 180 0C for Ih. The product was purified by LCMS to give 3-mercapto- [l,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid (450mg). ESI-MS:m/z 196.1 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 133081-24-0, 6-Hydrazinylnicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BRESSI, Jerome, C.; CHU, Shaosong; ERICKSON, Philip; KOMANDLA, Mallareddy; KWOK, Lily; LAWSON, John, D.; STAFFORD, Jeffrey, A.; WALLACE, Michael, B.; ZHANG, Zhiyuan; DAS, Sanjib; WO2010/19899; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18364-47-1, N-Methylpyridin-3-amine, 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, 18364-47-1, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 5.65 g (35.1 mmol) (IV-1), 75 mol of anhydrous pyridine and 4.19 g (38.7 mmol) of 3-methylaminopyridine was heated to reflux under argon for 8 hours, freed of the solvent under reduced pressure and the residue was stirred with 100 ml of ethanol and 0.1 mol of potassium carbonate at room temperature for one hour, the solid filtered off and the filtrate evaporated to dryness. The product was obtained from the residue by chromatography on silica gel using a mixture of dichloromethane and methanol. 1H-NMR (DMSO-d6, 600 MHz); delta=3.24 (s, 3H), 3.31 (s, 3H), 5.83 (s, 1H), 7.43-7-45 (m, 1H), 7.80-7.82 (m, 1H), 8.47-8.48 (m, 1H), 8.52 (m, 1H), 10.38 (s, 1H) ppm.1H-NMR (CD3CN, 400 MHz); delta=3.30 (s, 3H), 3.35 (s, 3H), 5.69 (s, 1H), 7.35-7-39 (m, 1H), 7.65-7.68 (m, 1H), 8.45-8.48 (m, 2H), 8.73 (br. s, 1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18364-47-1, its application will become more common.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; JANSEN, Johannes-Rudolf; HEIL, Markus; FISCHER, Reiner; WILCKE, David; WILLOT, Matthieu; ILG, Kerstin; EILMUS, Sascha; LOeSEL, Peter; ANDERSCH, Wolfram; (67 pag.)US2019/40042; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 17874-79-2, name is 5-(Methoxycarbonyl)picolinic acid, the common compound, a new synthetic route is introduced below. Product Details of 17874-79-2

A solution of 5-(methoxycarbonyl)picolinic acid (3.33 g, 18.4 mmol) in a mixture of pyridine (20 mL) and N,N-dimethylformamide (35 mL) was treated with 1,1′-carbonyldiimidazole (3.28 g, 20.2 mmol) at 45 C. for 2 hours. After cooling, 2,3-diaminobenzamide (HCl salt) (4.12 g, 18.4 mmol) was added and the mixture stirred at room temperature overnight. The mixture was concentrated and the residue used in the next step without further purification.

The synthetic route of 17874-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; US2009/30016; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 874302-76-8, 4-nitrophenyl 2-(pyridin-2-yldisulfanyl)ethyl carbonate, 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, Quality Control of 4-nitrophenyl 2-(pyridin-2-yldisulfanyl)ethyl carbonate, blongs to pyridine-derivatives compound. Quality Control of 4-nitrophenyl 2-(pyridin-2-yldisulfanyl)ethyl carbonate

To a solution of cabazitaxel (2.00 g, 2.40 mmol) and 2-(2- pyridinyldithio)ethanol p-nitrophenyl carbonate (915 mg, 2.60 mmol) in dichloromethane (48 mL) was added DMAP (439 mg, 3.60 mmol). The solution was stirred at room temperature overnight, then washed with 0.1N HCl (3 x 20 mL), brine (50 mL), and dried with sodium sulfate. The solvent was removed in vacuo, the the remaining residue purified by silica gel chromatography (2:1 petroleum ether:ethyl acetate) to give 4? (2.50 g, 2.38 mmol, 99% yield). LCMS m/z: 1049 (M + 1).

The synthetic route of 874302-76-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARVEDA THERAPEUTICS, INC.; BILODEAU, Mark T.; SIMCOX, Mary; WHITE, Brian H.; KADIYALA, Sudhakar; WOOSTER, Richard; (178 pag.)WO2017/180834; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1061357-89-8, 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 1061357-89-8 as follows.

A mixture of 2-bromo-5-fluoro-4-iodopyridine (6.8 g, 22.5 mmol), ethylene glycol (Sigma-Aldrich, St. Louis, MO, USA) (6.0 mL, 108.0 mmol), and potassium t-butoxide (Sigma-Aldrich, St. Louis, MO, USA ) (2.5 g, 22.7 mmol) in N-methylpyrrolidinone (10 mL) and THF (20 mL) was heated in a 60 oC bath. After 40 min, the mixture was removed from the oil bath and allowed to stir at RT for 14 h. The mixture was concentrated under reduced pressure. Additional potassium t-butoxide (0.5 g) and ethylene glycol (1.0 mL) were added and the reaction heated in an 80 oC bath for another 3 h then cooled to RT. ethyl acetate (200 mL) and water (150 mL) were added and the phases mixed and separated. The organic phase was washed with brine (75 mL) then evaporated to dryness under reduced pressure. Purification of the residue using silica gel chromatography (0 – 50% ethyl acetate in DCM) gave 2-((6-bromo-4-iodopyridin-3-yl)oxy)ethanol (3.1 g, 9.0 mmol, 40% yield). MS (ESI +ve ion) m/z: [M+1] = 343.8 / 345.8. 1H NMR (400 MHz, chloroFORM-d) _ 7.89 (s, 1H), 7.88 (s, 1H), 4.22 (td, J = 4.55, 6.36 Hz, 2H), 3.99-4.07 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1061357-89-8, its application will become more common.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Ning; FROHN, Michael J.; FU, Zice; LIU, Longbin; LIU, Qingyian; PETTUS, Liping H.; QIAN, Wenyuan; REEVES, Corey; SIEGMUND, Aaron C.; (362 pag.)WO2018/112094; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem