Pyridine-derivatives

Electric Literature of 1142363-52-7, 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.1142363-52-7, name is JNJ-40346527, molecular formula is C27H35N5O2, molecular weight is 461.5991, as common compound, the synthetic route is as follows.

Example 25 4-Cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide(1S)-(+)-10-camphorsulfonic acid salt A solution of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (52.4 mg, 0.113 mmol, as prepared in Example 15, step (h)) in EtOH (2 mL) was treated with (1S)-(+)-10-camphorsulfonic acid (26.4 mg, 0.113 mmol) at room temperature for 1 h. The solvents were evaporated in vacuo, and the residue was dried under high vacuum overnight. The solid was dissolved in a minimum amount of EtOH (1 mL) with sonication and heating. While warm, the solution was slowly treated with hexanes until first precipitate was seen at the surface of the solution. The mixture was allowed to stir 30 min at room temperature while material continued to precipitate. The solid was filtered and air-dried to afford the title compound (66.2 mg, 84%) as white crystals. 1H-NMR (CD3OD; 400 MHz): delta 9.17 (d, 1H, J=8.4 Hz), 8.10 (s, 1H), 7.95 (d, 1H, J=8.4 Hz), 6.39-6.32 (m, 1H), 3.76-3.64 (m, 1H), 3.38-3.34 (m, 2H), 2.80-2.75 (m, 1H), 2.75-2.65 (m, 1H), 2.54-2.45 (m, 2H), 2.40-2.30 (m, 1H), 2.25-2.18 (m, 2H), 2.10-2.00 (m, 2H), 1.98-1.86 (m, 3H), 1.76-1.66 (m, 4H), 1.65-1.56 (m, 1H), 1.47-1.38 (m, 7H), 1.30 (s, 6H), 1.15 (m, 9H), 0.87 (s, 3H). Mass spectrum (APCI, m/z): Calcd. for C27H35N5O2, 462.3 (M+H), found 462.3.

The chemical industry reduces the impact on the environment during synthesis 1142363-52-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Illig, Carl R.; Chen, Jinsheng; Meegalia, Sanath K.; Wall, Mark J.; US2009/105296; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 403-45-2 , The common heterocyclic compound, 403-45-2, name is 6-Fluoronicotinic acid, molecular formula is C6H4FNO2, 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.

Example 40A 6-Fluoro-nicotinic acid tert-butyl ester To a stirred and refluxed solution of 6-fluoro-nicotinic acid (0.092 g, 6.52 mmol) in benzene and 2-methyl-propan-2-ol (2:1, 15:7 mL) was added dropwise N,N-dimethylformamide di-tert-butyl acetal (8.2 mL, 29.6 mmol). The reaction mixture was refluxed for 3 hours, cooled to room temperature and partitioned between aqueous NaHCO3 and dichloromethane. The organic layer was washed with water and brine, dried (MgSO4), filtered, concentrated under reduced pressure and purified by flash chromatography with 15% to 30% ethyl acetate in hexane to provide the titled compound. MS (CI) m/z 197 (M+1)+; 1H NMR (300 MHz, CDCl3) delta ppm 8.82(d, 1H), 8.38(m, 1H), 6.98(d, 1H), 1.64 (s, 9H).

The synthetic route of 403-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2004/259843; (2004); A1;; ; Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2005/215784; (2005); 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. 131747-55-2, name is 2-Fluoro-3-(hydroxymethyl)pyridine. A new synthetic method of this compound is introduced below., name: 2-Fluoro-3-(hydroxymethyl)pyridine

Dissolve (2-fluoropyridin-3-yl)methanol in 85 mL of dichloromethane.In ice bath for 10 minutes, 21.7 mL (306.04 mmol) of thionyl chloride was slowly added dropwise. The reaction solution changed from yellow to brown and the reaction was completed. The reaction was continued for 2 h with ice bath. The reaction was complete with TLC monitoring. Continue the ice bath for a while and slowly add 100 mL of water. The N2 was blown, and the lye was absorbed into the exhaust gas. The mixture was extracted with methylene chloride (100 mL*3), washed with saturated brine (100 mL), dried over anhydrous MgSO4, and evaporated under reduced pressure to give 7.14 g of a brown liquid, which was used as needed.

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, 131747-55-2, 2-Fluoro-3-(hydroxymethyl)pyridine.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Li Song; Zheng Zhibing; Lin Feng; Gong Zehui; Lu Xinqiang; Zhou Xinbo; Zhong Wu; Xiao Junhai; Xie Yunde; Li Xingzhou; Wang Xiaokui; (24 pag.)CN107964011; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 188637-63-0, 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.188637-63-0, name is (6-Bromopyridin-2-yl)methanamine, molecular formula is C6H7BrN2, molecular weight is 187.0372, as common compound, the synthetic route is as follows.

[0667] 6-(Bromopyridin-2-yl)methylamine (4.0 g, 21.4 mmol) was added dropwise to acetic anhydride (10 ml) at 0 C. The reaction was warmed to room temperature and to the reaction was added p-toluenesulfonic acid (4.07 g, 20.4 mmol). The reaction was heated in a microwave reactor at 140C for 25 minutes. The reaction was concentrated in vacuo, the crude product was taken up in water, pH adjusted to -9 with iN aqueous NaOH, and extracted with twice with ethyl acetate. The organic layers were dried with Na2SO4, filtered, concentrated in vacuo, and purified by silica gel chromatography to give the title compound. MS (m/z) 213.06 [M+H].

Statistics shows that 188637-63-0 is playing an increasingly important role. we look forward to future research findings about (6-Bromopyridin-2-yl)methanamine.

Reference:
Patent; GILEAD SCIENCES, INC.; BRIZGYS, Gediminas; CANALES, Eda; CHOU, Chien-hung; GRAUPE, Michael; HU, Yunfeng, Eric; LINK, John, O.; LIU, Qi; LU, Yafan; SAITO, Roland, D.; SCHROEDER, Scott, D.; SOMOZA, John, R.; TSE, Winston, C.; ZHANG, Jennifer, R.; WO2014/134566; (2014); A2;,
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. 39891-09-3, name is 2-Chloropyridine-5-acetonitrile. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 39891-09-3

15.2 g 2-chloropyridin-5-ylacetonitrile was added to a 250 ml four-mouthed flask. Add 150 ml ethanol. 10ml 98% concentrated sulfuric acid. Heat to reflux. Reflux reaction for 4 hours, reaction finishes, prolapsed ethanol, add 100 g water to stir, is neutral pH the sodium carbonate is used to regulate, filter, to obtain 2-chloro pyridine ethyl acetate 13 g.

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, 39891-09-3, 2-Chloropyridine-5-acetonitrile.

Reference:
Patent; Li, Weizhong; Zhao, Jing; (13 pag.)CN105669584; (2016); A;,
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. 716362-10-6, name is 6-Chloro-4-methoxynicotinic acid, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

Triethylamine (7.0 mL, 51 mmol) was added to a suspension of 6-chloro-4-methoxynicotinic acid (2.615 g, 13.94 mmol, Intermediate 132) in MeCN (93 mL). N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (3.74 g, 19.5 mmol), HOBt (2.64 g, 19.5 mmol), and N,O-dimethylhydroxylamine hydrochloride (2.05 g, 21.0 mmol) were added, and the resulting mixture was stirred at rt for 3 days. After this time, the mixture was concentrated, and the residue was dissolved in EtOAc and water. The layers were mixed and separated, and the aqueous layer was extracted five times with EtOAc. The organic layers were combined, dried with anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0?20% EtOAc/hexanes) to provide the title compound.

The synthetic route of 716362-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Wolin, Ronald L.; Fourie, Anne M.; Xue, Xiaohua; (85 pag.)US2019/382350; (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. 52311-50-9, name is 2-Chloro-4-ethoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-4-ethoxypyridine

A solution of [(2R,5R)-5-hydroxy-2-methylpiperidin-l-yl][2-(2H- 1,2,3 -triazol-2- yl)phenyl]methanone (0.025 g, 0.087 mmol) in DMF (1 mL) was treated with sodium hydride (3.1 mg, 0.131 mmol). After stirring ~20 minutes, 2-chloro-4-ethoxypyridine (16.5 g, 0.105 mmol) was added and the reaction was heated to 50 C overnight. Additional sodium hydride (1.6 mg, 0.065 mmol) was added, and the reaction was heated to 80 C for 4 h, then quenched with saturated aqueous ammonium chloride and diluted with water. The mixture was extracted 3x with ethyl acetate and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-3% methanol in dichloromethane) to provide the title compound. FIRMS m/z (Mu+Eta) 408.2016 found, 408.2030 required.

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, 52311-50-9, 2-Chloro-4-ethoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2014/137883; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 940943-37-3, S-(2-(6-(4-(3-(Dimethylamino)propoxy)phenylsulfonamido)pyridin-3-yl)-2-oxoethyl) ethanethioate, 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 940943-37-3, blongs to pyridine-derivatives compound. Product Details of 940943-37-3

[0200] A 1 : 1 mixture of Compound 1 (0.3006 g) and L-malic acid (0.0893 g) was dissolved in 10 mL methanol at 70 0C. Oil formed upon cooling to ambient temperature. Seeds (Malate A) were added and the sample was stirred, overnight, at ambient temperature. Light yellow solids were observed and obtained by vacuum filtration. The solids were left to air dry overnight (0.2803 g; yield 72%, based on unsolvated weight).

The synthetic route of 940943-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2008/73733; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1095823-39-4, 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 1095823-39-4, name is 5-Chloro-4-(trifluoromethyl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A 20 mL vial was charged with compound A.5 (191.8 mg, 0.0006561 mol), methylene chloride (3.0 mL), a 2.0 M solution of oxalyl chloride in methylene chloride (390 muL) and DMF (10.0 muL, 0.000129 mol). The reaction mixture was stirred for 15 minutes at rt, then concentrated in vacuo and the resultant residue was taken up in acetonitrile (3.0 mL). To this solution was added a solution of compound A.6 (129 mg, 0.000656 mol) and pyridine (0.5 mL, 0.006 mol) in acetonitrile (1.5 mL). The reaction mixture was stirred at RT overnight. The solvent was removed under reduced pressure, and the residue was purified by combiflash (0-30% EtOAc/CH2Cl2) to give compound A.7 in 49% yield. LCMS: m/z 471 [M+1]+.

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 1095823-39-4, 5-Chloro-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2009/36419; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-06-6, 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 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate. This compound has unique chemical properties. The synthetic route is as follows.

5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide: To 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (200 mg, 0.869 mmol) and methylamine (135 mg, 11.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide (130 mg, 65%) as an off-white solid.

According to the analysis of related databases, 886365-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem