Category: pyridine-derivatives

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. 55240-51-2, name is 2-Phenylisonicotinic acid. A new synthetic method of this compound is introduced below., Safety of 2-Phenylisonicotinic acid

General procedure: To a solution of cyanoacetic acid (340 mg, 4.0 mmol) and 1,1-dioxo-1H-1lambda6-benzo[b]thiophen-6-ylamine (362 mg, 2.0 mmol) in 10 mL of CH2Cl2 was added DIPEA (774 mg, 6.0 mmol). HBTU (1.14 g, 3.0 mmol) was added at 0 C. The resulting mixture was stirred at r.t. for 28 h. The reaction mixture was diluted with CH2Cl2 (80 mL) and washed with water (20 mL). The organic layer was separated and dried with anhydrous Na2SO4. The solution was concentrated to give a crude product, which was purified with silica gel column (EtOAc/hexane = 1/1) to obtain the desired product (400 mg, 81%) as a yellow solid (mp 207-208 C). HPLC purity 98.6% (tR = 10.93 min). 1H NMR (600 MHz, DMSO-d6) delta 10.79 (s, 1H), 8.04 (s, 1H), 7.67-7.69 (m, 1H), 7.60 (d, 1H, J = 7.2 Hz), 7.57 (d, 1H, J = 7.8 Hz), 7.30 (d, 1H, J = 7.2 Hz), 3.98 (s, 2H). 13C NMR (150 MHz, DMSO-d6) delta 162.0, 140.7, 137.3, 132.8, 130.3, 126.7, 126.1, 123.4, 115.6, 111.4, 27.0. HRMS (ESI) calcd for C11H19N2O3S 249.0328 (M + H)+, found 249.0330.

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, 55240-51-2, 2-Phenylisonicotinic acid.

Reference:
Article; Chen, Haijun; Yang, Zhengduo; Ding, Chunyong; Chu, Lili; Zhang, Yusong; Terry, Kristin; Liu, Huiling; Shen, Qiang; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 498 – 507;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 168173-56-6 ,Some common heterocyclic compound, 168173-56-6, molecular formula is C6H5BrClN, 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: 4-Amino-5,5-disubstituted furan-2(5H)-one 1a-e (2 mmol) was dissolved in dry MeCN (25 mL) in a 50-mL round-bottom flask. The solution was cooled to 0 C by an ice-water bath, then Cs2CO3 (1.304 g, 4 mmol) was added slowly. The mixture was warmed to r.t. and stirred for 4 h. ArCH2Cl 2a-h (2.4 mmol) was added and the mixture was stirred for 12 h under reflux. The mixture was cooled to r.t. and the solid material was filtered off. The filtrate was concentrated in vacuo and the crude product was purified by flash column chromatography (silica gel, 200-300 mesh, petroleum/EtOAc 4:1 to 3:2) to give compounds 3a-x and 4a-f.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,168173-56-6, its application will become more common.

Reference:
Article; Yu, Zhao; Xinlei, Liu; Weiwei, Wang; Rui, Geng; Wang, Mingan; Synthesis; vol. 50; 20; (2018); p. 4055 – 4062;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 171178-45-3, 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 171178-45-3, name is tert-Butyl (6-chloropyridin-3-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Preparation of tert-butyl 6-chloro-4-fluoropyridin-3-ylcarbamate To a -63 C. solution of tert-butyl 6-chloropyridin-3-ylcarbamate (24.99 g, 109.3 mmol) and TMEDA (39 mL, 260.0 mmol, Aldrich) in diethyl ether (700 mL) was added a 1.6M n-butyl lithium solution in hexane (193 mL, 308.8 mmol, Aldrich) over a period of 30 minutes while maintaining the temperature of the reaction at -60 to -50 C. The reaction was stirred at -60 C. for an additional 10 minutes after the addition was complete then warmed to -10 C. and stirred at -25 to -10 C. for 2.0 hours. The reaction was cooled to -60 C. and a solution of N-fluorobenzenesulfonimide (53.49 g, 169.6 mmol, Aldrich) in tetrahydrofuran (155 mL) was added while keeping the temperature below -50 C. It precipitated on addition and stirring became difficult. The reaction was then allowed to slowly warm to 0 C. over 1 hour. The reaction was quenched with saturated ammonium chloride solution (400 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, and solvent was removed at reduced pressure to give an oily brown solid. The material was passed through a column of silica gel with 20% ethyl acetate/hexane. The 6-chloro-4-fluoropyridin-3-ylcarbamate was obtained as a yellow solid. (15.88 g, 59% yield). 1H NMR (CDCl3) delta 9.09 (1H), 7.12 (1H), 6.55 (1H), 1.54 (s, 9H).

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 171178-45-3, tert-Butyl (6-chloropyridin-3-yl)carbamate.

Reference:
Patent; Pfizer Inc; US2007/249615; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 874959-68-9, 5-Bromopyridine-2-sulfonyl chloride, 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, SDS of cas: 874959-68-9, blongs to pyridine-derivatives compound. SDS of cas: 874959-68-9

5-Bromo-N-(4-methoxy-6-methyl-pyrimidin-2-yl)pyridine-2-sulfonamide (Intermediate Z) (0442) [00301] To a solution of 5-bromopyridine-2-sulfonyl chloride (1.00 g, 3.90 mmol, Intermediate W) in pyridine (10 mL) was added 4-methoxy-6-methyl-pyrimidin-2-amine (542 mg, 3.90 mmol). The reaction mixture was stirred at 15 C for 16 hrs. On completion, the reaction mixture was concentrated in vacuo and the residue was triturated with dichloromethane:methanol = 5:1 to give the title compound which was used directly without further purification. LCMS: (ES+) m/z (M+H)+ = 360.8, tR= 0.965.1H NMR (400MHz, DMSO- d6) delta = 12.96 (br. s., 1H), 8.75 (d, J = 1.6 Hz, 1H), 8.26 (dd, J = 1.8, 8.3 Hz, 1H), 7.99 (d, J = 8.3 Hz, 1H), 6.15 (s, 1H), 3.43 (s, 3H), 2.23 (s, 3H).

The synthetic route of 874959-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; MOYER, Mikel P.; SAIAH, Eddine; (264 pag.)WO2017/156181; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 120034-05-1 , The common heterocyclic compound, 120034-05-1, name is Methyl 5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate, molecular formula is C7H6BrNO3, 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.

Methyl 5-bromo-2-oxo-l,2-dihydropyridine-3-carboxylate (Combi-Blocks, CAS: 120034-05-1, 0.100 g, 0.431 mmol) was dissolved in THF (4.31 mL) and added dropwise to a 0 C solution of lithium aluminum hydride (0.082 g, 2.155 mmol) in THF (4.31 mL). The reaction mixture was stirred at 0 C for 30 min, then allowed to warm to room temperature and stirred for 2.5 h. Saturated aqueous NH4CI solution (8 mL) was slowly added to the reaction mixture, followed by ethyl acetate (8 mL). The phases were separated, the aqueous phase was extracted with additional ethyl acetate (2×10 mL). The combined organic phases were dried over sodium sulfate and filtered, and excess solvent was evaporated off to afford 5-bromo-3-(hydroxymethyl)pyridin-2(lH)-one (34.1 mg, 0.159 mmol, 36.8% yield) as a white solid. LCMS MH+: 203.9. HPLC Ret. Time 0.47 min. Method Bl . NMR (400 MHz, METHANOLS) delta 7.67 (dt, J=2.7, 1.4 Hz, 1H), 7.51 (d, J=2.7 Hz, 1H), 4.49 (s, 2H).

The synthetic route of 120034-05-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; HAQUE, Tasir Shamsul; WHITELEY, Brian K.; GILMORE, John L.; (192 pag.)WO2019/28302; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 97509-75-6, 3-Fluoropicolinonitrile, 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 97509-75-6, blongs to pyridine-derivatives compound. Product Details of 97509-75-6

Pre aration 86A: 3-Fluoro-4-iodopicolinonitrile[00297] To a solution of diisopropylamine (2.80 ml, 19.66 mmol) in THF (Volume: 201 ml) cooled to -78 °C was added n-butyllithium (7.86 ml, 19.66 mmol) dropwise. The dry ice/acetone bath was replaced with an ice water bath and reaction mixture was stirred at 0 °C for 25 min, and then re-cooled to -78 °C. In a separate flask, a solution of 3- fluoropicolinonitrile (1.5 g, 12.29 mmol) in THF (50 mL) was cooled to -78 °C, and then LDA (130 mL, 1.0 equiv) was added. The solution turned dark red. After 35 min, iodine (3.43 g, 13.51 mmol) was added rapidly. The reaction mixture was stirred for 45 min, then quenched with H20. Layers were separated and the aqueous phase extracted with CH2CI2 (2X). Organics combined, dried over Na2S04, filtered, and concentrated to afford a brown residue. The crude material was dissolved in a minimal amount of CH2CI2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (80 g column, 60 mL/min, 0-20percent EtOAc in hexanes over 23 min, tr = 18 min) gave the title compound (1.7 g, 6.79 mmol, 55.2percent yield) as a brown solid.

The synthetic route of 97509-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); 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.1229006-21-6, name is Methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate, molecular formula is C26H26F2N2O7, molecular weight is 516.4907, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate

Example 2e Methyl 5-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-1-[2-hydroxy-2-(methyloxy)ethyl]-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate (in equilibrium with the corresponding aldehyde) Methyl 1-[2,2-bis(methyloxy)ethyl]-5-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate 25 (11.6 g) was treated with 90% formic acid (250 mL) at 40 C. for ?12 hours (monitored by LC-MS). After the solvents were evaporated at <40 C., the residue was re-dissolved in EtOAc (?1 L) and the resulting solution was washed with NaHCO3 and brine. The organic phase was then dried over Na2SO4. After evaporation of solvents, the titled compounds 26 and 27 were obtained as an approximate 80/20 equillibrium mixture (10.57 g). 1H NMR (400 MHz, DMSO-d6) 5 ppm 10.3 (m, 1H), 9.47 (s, aldehyde-H. ?0.2H)), 8.4 (m, 1H), 7.3 (s, 6H), 7.2 (m, 1H), 7.0 (m, 1H), 6.3 (m, 2H), 5.1 (s, 3H), 4.9 (m, 1H), 4.5 (m, 3H), 3.9 (m, 2H), 3.8 (s, 3H). LC-MS, for 26 (M+H+), calcd 503, obsd 503; for 27 (M+H2O+H+), cald 489, obsd 489. At the same time, in my other blogs, there are other synthetic methods of this type of compound,1229006-21-6, Methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate, and friends who are interested can also refer to it. Reference:
Patent; SHIONOGI & CO., LTD.; ViiV Healthcare Company; Kawasuji, Takashi; Nagamatsu, Daiki; (30 pag.)US9242986; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22282-72-0, 2-Oxo-1,2-dihydropyridine-4-carboxylic acid, 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, Recommanded Product: 22282-72-0, blongs to pyridine-derivatives compound. Recommanded Product: 22282-72-0

Preparative Example 4.30 4-[(4-iodo- lH-pyrazol- 1 -yl)methyl]py Step 1 : Borane-THF (29 mL, 1.0 M) was added to a solution of 2-oxo-l,2- dihydropyridine-4-carboxylic acid (1 g, 7.19 mmol) in THF (15 mL) at 0 C. The mixture was stirred at 25 C for 2 hours. Methanol was added and the mixture was concentrated under reduced pressure to afford 4-(hydroxymethyl)pyridin-2(lH)-one. MS ESI calc’d. for C6H8 02 [M + H]+ 126, found 126. XH NMR (400 MHz, CD3OD) delta 7.40 (d, J= 6.8 Hz, 1H), 6.58 (s, 1H), 6.38 (d, J= 6.4 Hz, 1H), 4.52 (s, 2H).

The synthetic route of 22282-72-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michele, R.; ALTMAN, Michael, D.; ROMEO, Eric, T.; VITHARANA, Dilrukshi; CASH, Brandon; SIU, Tony; ZHOU, Hua; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; HAIDLE, Andrew, M.; CHILDERS, Kaleen Konrad; MADDESS, Matthew, L.; REUTERSHAN, Michael, H.; DUCHARME, Yves; GUERIN, David. J.; SPENCER, Kerrie; BEAULIEU, Christian; TRUONG, Vouy Linh; GUAY, Daniel; NORTHRUP, Alan, B.; TAOKA, Brandon, M.; LIM, Jongwon; FISCHER, Christian; BUTCHER, John, W.; OTTE, Ryan, D.; SUN, Binyuan; WO2013/192125; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 18437-58-6 , The common heterocyclic compound, 18437-58-6, name is 4-Amino-2-picoline, molecular formula is C6H8N2, 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.

1003651 Step A: 2-Methylpyridin-4-amine (0.28 g, 2.6 mmol) was placed in THF (5 mL) and cooled to -78C. t-BuLi (1.5 mE, 2.6 mmol) was added dropwise, and the solution was warmed to 0C for 30 minutes. This solution was then added dropwise to a -78C THF solution (5 mL) of (5)-i -(2-(tert-butyldimethylsilyloxy)- 1 -(4-chloro-3 -fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2( 1 11)-one (0.070 g, 0.13 mmol). The reaction was stirred for an additional 30 minutes at -78C, then poured into water, and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated to give the crude product, which was purified by column chromatography (500:10-500:20 DCM/MeOH) to give the product (5)-i -(2-(tert-butyldimethylsilyloxy)- 1 -(4-chloro-3 – fluorophenyl)ethyl)-4-(2-((2-methylpyridin-4-yl)amino)pyrimidin-4-yl)pyridin-2( 111)-one(0.028 g, 38% yield).

The synthetic route of 18437-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James F.; CHICARELLI, Mark Joseph; GARREY, Rustam Ferdinand; GAUDINO, John; GRINA, Jonas; MORENO, David A.; MOHR, Peter J.; REN, Li; SCHWARZ, Jacob; CHEN, Huifen; ROBARGE, Kirk; ZHOU, Aihe; WO2013/130976; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 609-70-1, 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.609-70-1, name is 4-Hydroxynicotinic acid, molecular formula is C6H5NO3, molecular weight is 139.11, as common compound, the synthetic route is as follows.

7.92 (1H, d, SPC238 8.57 (1H, s, SPC239 PREPARATION OF THE STARTING MATERIAL To 80 ml. of dichloromethane solution containing 9.8 g. of 4-hydroxynicotinic acid and 10 ml. of triethylamine was added dropwise 7 ml. of thionyl chloride with stirring under ice-cooling over a period of 20 minutes and the mixture was stirred for 2 hours at room temperature. The crystals thus formed were recovered by filtration, washed with a small amount of dichloromethane, and then dried to provide 4-hydroxynicotinoyl chloride.

The chemical industry reduces the impact on the environment during synthesis 609-70-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US3953428; (1976); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem