Tag: M.W:100-200

Application of 120739-77-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine, molecular formula is C8H11ClN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2): Synthesis of N-(6-chloropyridin-3-yl)methylene)-N-ethyl-1-(methylthio)-2-nitrovinylidene amine To a 100 ml three necked round bottom flask, N-(6-chloropyridin-3-yl-methylene)ethylamine (17.0 g, 0.1 mol), 1,1-bis(methylthio)-2-nitroethene (15.0 g, 0.09 mol), anhydrous ethanol (50 mL) were added. The mixture was refluxed until full convention and cooled to r.t., The reaction was concentrated with reduced pressure to obtain a crude product as dense liquid, which was purified by column chromatography to yield 5.3 g N-(6-chloropyridin-3-yl-methylene)-N-ethyl-1-(methylthio)-2-nitrovinylidene amine in 18.5% yield.

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 120739-77-7, N-((6-Chloropyridin-3-yl)methyl)ethanamine.

Reference:
Patent; EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY; US2010/298346; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52334-51-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 52334-51-7, name is 3-Amino-5-methylpyridin-2(1H)-one, molecular formula is C6H8N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[00266] Example 102: To a suspension of Example 12 (42 mg, 0.081 mmol) in sodium hydroxide (806 mu, 0.806 mmol) was added Example 102A (10 mg, 0.081 mmol). The reaction mixture was stirred at 40 C for over the weekend. The reaction was quenched with 1 N HC1 and MeOH. The organic layer was reduced in vacuo, and was purified using a 10 minutes gradient from 0 to 100%> B (Column: PHENOMENEX Axia Luna 100×20 mm 5u (10 min gradient). Solvent A: 10% ACN-90% H2O-0.1% TFA, Solvent B: 90% ACN-10% H2O-0.1% TFA) to give Example 102 (19 mg, 32% yield). lH NMR (400 MHz, MeOD) delta ppm 1.55 (s, 3H), 1.56 (s, 3H), 2.50 (s, 3 H), 3.25 – 3.27 (m, 1 H), 3.88 (d, J = 9.85 Hz, 1 H), 6.78 (d, J = 8.34 Hz, 1 H), 6.96 – 6.99 (m, 2 H), 7.09 – 7.13 (m, 1 H), 7.17 (d, J = 9.09 Hz, 2 H), 7.50 – 7.55 (m, 3 H), 7.93 (d, J = 8.08 Hz, 1 H), 7.98 (m, 1 H), 8.16 (m, 1 H). LCMS (ESI) m/z 590.0 (M+H)+, RT = 4.26 min (Method C).

According to the analysis of related databases, 52334-51-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; L’HEUREUX, Alexandre; HIEBERT, Sheldon; HU, Carol; LAM, Patrick Y.S.; LLOYD, John; PI, Zulan; QIAO, Jennifer X.; THIBEAULT, Carl; TORA, George O.; YANG, Wu; WANG, Yufeng; WANG, Tammy C.; BOWSHER, Michael S.; RUEL, Rejean; WO2014/22343; (2014); 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.73583-41-2, name is 4-Bromo-3-chloropyridine, molecular formula is C5H3BrClN, molecular weight is 192.441, as common compound, the synthetic route is as follows.Application In Synthesis of 4-Bromo-3-chloropyridine

Step 1: Preparation of 3-chloro-4-((trimethylsilyl)ethynyl)pyridine A mixture of 4-bromo-3-chloropyridine (2 g, 10.5 mmol), bis(triphenylphosphine)palladium(II) chloride (0.37 g, 0.52 mmol), copper iodide (0.2 g, 1.05 mmol) in triethylamine (20 mL) was degassed and re-filled with nitrogen (2*). Then ethynyltrimethylsilane (4.4 mL, 31.4 mmol) was added dropwise by a syringe. After the addition, the reaction mixture was stirred at 60 C. for 18 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL*2). The combined organic phases were washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography (Biotage, 40 g silica, eluted with ethyl acetate in petroleum ether from 10% to 15%) to give 3-chloro-4-((trimethylsilyl)ethynyl)pyridine (1.47 g, 7.03 mmol, 67%) as a yellow oil. LCMS (ESI) m/z: 210.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73583-41-2, 4-Bromo-3-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 129432-25-3, 2,6-Dichloro-4-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, HPLC of Formula: C6H6Cl2N2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H6Cl2N2

To a solution of 2,6-dichloro-4-methylpyridin-3-amine (3 g, 17 mmol) in toluene (50 mL) was added KOAc (2 g, 20.4 mmol) and Ac20 (6.9 g, 68 mmol). The mixture was stirred at 70 C for 48 h. The mixture was cooled to room temperature, and then poured into ice water (100 mL). The water was extracted with EtOAc (60 mL X 3). The combined organic phases were concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 25% EtOAc in petroleum ether to afford N-(2,6-dichloro-4-methylpyridin-3-yl) acetamide (842 mg, 22%) as a yellow solid. MS m/z 219.0, 221.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,129432-25-3, 2,6-Dichloro-4-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); 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.33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, molecular weight is 138.55, as common compound, the synthetic route is as follows.COA of Formula: C6H3ClN2

Example 15-Cyano-pyridine-2-carboxylic acid A 2 L stirred autoclave was charged under argon with PdC12(dppp) (2.13 g, 3.61 mmol), 6- chloro-nicotinonitrile (100 g, 0.722 mol), tert-butanol (800 ml), deionized water (200 ml) andtriethylamine (250 ml, 1.8 mol). The reaction vessel was closed, purged three times with carbonmonoxide (10 bar) and finally charged with carbon monoxide to 15 bar. The mixture was stirredvigorously at 60C under constant pressure for 10 h; after this time no more carbon monoxideabsorption was observed. The reaction mixture was concentrated on a rotary evaporator such thatthe volatile organic components were removed. The resulting aqueous phase was filtered,extracted with dichloromethane and treated with active charcoal. After filtration, the pH of thesolution was reduced under stuffing at 60C to ca. 0.7 by dropwise addition of hydrochloric acid.The resulting suspension was stirred at room temperature over night and then filtered. The filter cake was rinsed with water and dried in vacuo to constant weight to afford 5-cyano-pyridine-2- carboxylic acid (98.95 g) as a white solid, MS: mlz = 104 [M-C021, m.p.: 207 C (dcc).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-28-7, 6-Chloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FETTES, Alec; MARTY, Hans-Peter; SCALONE, Michelangelo; WO2014/173917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83766-88-5, 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.83766-88-5, name is 2-(tert-Butoxy)pyridine, molecular formula is C9H13NO, molecular weight is 151.21, as common compound, the synthetic route is as follows.

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

Statistics shows that 83766-88-5 is playing an increasingly important role. we look forward to future research findings about 2-(tert-Butoxy)pyridine.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100202-78-6, 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 100202-78-6, name is 2-(Bromomethyl)-6-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The commercially available starting material 1 (1.0mmol) was suspended in acetonitrile (10mL) containing K2CO3 (2.0mmol). The reaction was treated with an appropriately substituted arylalkyl derivatives 2a-o and 4a-4h (1.2mmol) and heated under reflux for 8h. The reaction progress was monitored using silica gel TLC with DCM/MeOH as mobile phase. Upon completion, the acetonitrile was evaporated in vacuo and the mixture was then poured into water, which was extracted with DCM, washed with brine, dried over anhydrous Na2SO4 and purified by chromatography (DCM/MeOH) on silica gel to afford the target compounds.

According to the analysis of related databases, 100202-78-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Zhi-Min; Cai, Pei; Liu, Qiao-Hong; Xu, Ding-Qiao; Yang, Xue-Lian; Wu, Jia-Jia; Kong, Ling-Yi; Wang, Xiao-Bing; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 282 – 297;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98353-08-3, 5-Ethoxypicolinic 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, Safety of 5-Ethoxypicolinic acid, blongs to pyridine-derivatives compound. Safety of 5-Ethoxypicolinic acid

5-ethoxypicolinic acid (80mg, 0.479 mmol) was slurried in N,N-Dimethylformamide (dry) (2 ml), DIPEA (0.100 ml, 0.574 mmol) was added followed by HATU (200 mg, 0.526 mmol). After 15 mins 2-chloroaniline (0.056 ml, 0.526 mmol) was added to the brown suspension and the resulting reaction mixture stirred at room temperature for 20 hours. The reaction mixture was evaporated to dryness. This mixture was added to a cold water/ sat. sodium bicarbonate mixture (2:1, 20 ml) and DCM 20 mL. The product was extracted and the layers were separated over a phase separator. The filtrate was evaporated to dryness to give the product as a brown oil which solidified on standing. The product was purified further by reveleris 12 gram column using heptane-EtOAc gradient (0 to 25%) to afford a white solid. Used as such.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98353-08-3, 5-Ethoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; FORSCHUNGSVERBUND BERLIN E.V.; UNIVERSITY OF OULU; KRAUSS, Stefan; NAZARE, Marc; ANUMALA, Upendra Rao; LEHTIO, Lari; WAALER, Jo; HOLSWORTH, Dan; WEGERT, Anita; LEENDERS, Ruben Gerardus George; (99 pag.)WO2018/118868; (2018); 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.700811-29-6, name is 2-Chloro-4-hydrazinopyridine, molecular formula is C5H6ClN3, molecular weight is 143.5742, as common compound, the synthetic route is as follows.Quality Control of 2-Chloro-4-hydrazinopyridine

5.25 g (13.3 mmol) of (7), 3.78 g (17.5 mmol) of (2-Chloro-pyridin-4-yl)-hydrazine and 13.3 ml (74.7 mmol) of DIEA were suspended in 26.6 ml of NMP. The reaction mixture was capped and heated to 220 degrees C. via microwave irradiation. After 6 min., the reaction mixture was allowed to cool to RT. The reaction mixture was then poured onto a saturated aqueous solution of sodium bicarbonate. This aqueous phase was diluted with EtOAc and the layers were separated. The organic was dried over MgSO4, filtered and evaporated to dryness. This crude material was chromatographed on 6 inches of silica gel and eluted with 5-9% MeOH/CH2Cl2. The still slightly crude material was recrystallized from EtOAc/Hexane. Yield: 1.38 g, approximately 23%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,700811-29-6, 2-Chloro-4-hydrazinopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Salituro, Francesco; Ledeboer, Mark; Ledford, Brian; Wang, Jian; Pierce, Albert; Duffy, John; Messersmith, David; US2006/63756; (2006); 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. 1137-67-3, name is 2-(Pyridin-3-yl)-1H-benzo[d]imidazole. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C12H9N3

Step 2: 8-Fluoro-4-((2-(pyridin-3-yl)-1H-benzo[d]imidazol-1-yl)methyl)quinolin-2(1H)-one Sodium hydride (60% in mineral oil, 117 mg, 2.9 mmol) was added to 2-(pyridin-3-yl)-1H-benzo[d]imidazole (191 mg, 0.98 mmol) in DMF (5 mL) and stirred at RT for 15 min. 4-(Bromomethyl)-8-fluoroquinolin-2(1H)-one (300 mg, 1.2 mmol) was then added as a solid and the resulting mixture was stirred at RT for 18 h. The crude mixture was purified by preparative HPLC (ACN/water) to yield 60 mg (16%) of 8-fluoro-4-((2-(pyridin-3-yl)-1H-benzo[d]imidazol-1-yl)methyl)quinolin-2(1H)-one as a pale yellow. 1H NMR (400 MHz, DMSO-d6, TFA salt) delta 11.86 (s, 1H), 8.93 (s, 1H), 8.72 (d, 1H), 8.13 (d, 1H), 7.86 (d, 1H), 7.69 (d, 1H), 7.64 (d, 1H), 7.59-7.57 (m, 2H), 7.40-7.36 (m, 2H), 7.26 (m, 1H), 5.94 (s, 2H), 5.53 (s, 1H). LCMS: 371 (M+H)+.

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, 1137-67-3, 2-(Pyridin-3-yl)-1H-benzo[d]imidazole.

Reference:
Patent; KALYPSYS, INC.; US2008/139558; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem