Category: pyridine-derivatives

Synthetic Route of 1335210-23-5, 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. 1335210-23-5, name is 1-(2,2-Dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid, molecular formula is C13H17NO8, 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.

Step 1; A suspension of compound 11-A (965 mg, 3.061 mmol), 2,4,6- trifiuorobenzylamine (493 mg, 3.06 mmol), and HATU (1402 mg, 3.688 mmol) in CH2C12 (15 mL) was stirred in 0 C as DIEA (2 mL, 11.48 mmol) was added.After 1.5 hours at 0 C, the reaction mixture was diluted with ethyl acetate, and washed with water (twice). After the aqueous fractions were extracted with ethyl acetate, the organic fractions were combined, dried (Na2S04), and concentrated. The residue was purified by CombiFlash (40 g column) using hexanes-ethyl acetate as eluents to obtain compound 11-B. 1H NMR (400 MHz, Chloroform-d) delta 10.30 (t, J = 5.9 Hz, 1H), 8.40 (s, 1H), 6.79 – 6.51 (m, 2H), 4.65 (d, J = 5.6 Hz, 2H), 4.48 (t, J = 4.8 Hz, 1H), 4.01 (d, J = 4.8 Hz, 2H), 3.97 (s, 3H), 3.94 (s, 3H), 3.38 (s, 6H). 19F NMR (376 MHz, Chloroform-d) delta – 109.07 – -109.35 (m, IF), -1 1 1.93 (t, J = 6.9 Hz, 2F). LCMS-ESI+ (m/z): [M+H]+ calculated for C20H22F3N2O7: 459.14; found: 459.2.

According to the analysis of related databases, 1335210-23-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; JI, Mingzhe; LAZERWITH, Scott E.; PYUN, Hyung-Jung; WO2015/6731; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 885167-81-7, 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. 885167-81-7, name is 6-Bromo-5-methylnicotinaldehyde, molecular formula is C7H6BrNO, 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.

Embodiment 69 (E)-2-((6-(3-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylstyryl)-5-methy lpyridin-3-yl)methylamino)-3-hydroxypropanoic acid 69 Synthetic route Synthesis of compound 69-a Compound 15-b (850mg, 2.2mmol) and 6-bromo-5-methyl nicotine aldehyde (300mg, 1.5mmol) were dissolved in a mixed solvent of 1,4-dioxane (20mL) and water (2mL), followed by addition of [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (30mg, 0.03mmol) and sodium carbonate (397mg, 3.7mmol). After the reaction system was purged three times with nitrogen, the reaction solution was heated to 80C and stirred for 12 hours. The reaction solution was cooled to room temperature and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to give compound 69-a as a yellow solid (220mg, yield 40%). LC-MS (ESI): m/z = 372 [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 885167-81-7, 6-Bromo-5-methylnicotinaldehyde.

Reference:
Patent; Guangzhou Maxinovel Pharmaceuticals Co., Ltd.; WANG, Yuguang; XU, Zusheng; WU, Tianzhi; HE, Min; ZHANG, Nong; (113 pag.)EP3483142; (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. 19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 19337-97-4

Under N2 atmosphere, HOBt hydrate (0.31 g, ca. 2.0 mmol, MW = 125.12 + ca. 12 percent H20), EDCI (0.33 g ca. 2.1 mmol, MW = 155.25) and (£)-3-(3-pyridyl)acrylic acid (0.33 g, 2,2 mmol, MW = 149.137) were added sequentially to a cooled (0 °C) solution of 8 (0.515 g. 2 mmol, MW = 256.392) in dry CH2CI2 (7 mL). after stirring at 0 °C for 10 min N- methylmorpholine (0.44 mL) was added drop-wise under stirring at 0 °C. The mixture was then allowed to reach room temperature under stirring and stirred until completion of the reaction (monitored by TLC). A saturated aqueous solution of NaHC03 (15 mL) was added and stirred vigorously for 5 min. The aqueous layer was extracted with CH2CI2 (5 mL, 3 times). The combined organic extracts and solution were washed with brine (50 mL) and dried (MgS04). The solvent was evaporated in vacuo and the residue purified by FC (EtOAc) to give acrylamide 9 (0.643 g, 83 percent, MW = 387.513) as a yellow oil that was used directly in the following reaction. Solution of compound 9 (0.39 g, 1 mmol, MW = 387.513) in 4M HCI/dioxane solution (1 .0 mL) was stirred at 20 °C for 30 min (monitored by TLC). After solvent evaporation in vacuo, salt 9a (0.299 g, 92.3percent, MW = 323.889) was obtained as a white solid; it was used in the next step without purification. (0187) 1H NMR (400 MHz, CD3OD): delta = 9.15 (d, 1 H, J = 1 .5 Hz), 8.91 (dt, 1 H, J = 8.3 Hz, 1 .6 Hz), 8.86 (d, 1 H, J = 5.7 Hz), 8.17 (dd, 1 H, J = 8.2 Hz, 5.8 Hz), 7.67 (d, 1 H, J = 15.8 Hz), 7.06 (d, 1 H, J = 15.8 Hz), 3.62 (t, 2H, J = 6.1 Hz), 3.45 (t, 2H, J = 7.1 Hz), 3.35-3.31 (m, 3H), 3.19- 3.09 (m, 2H), 2.09-1 .99 (m, 2H), 1 .95-1 .84 (m, 4H). (0188) Yield: 0.53g (82percent), white solid, 1 H NMR (400 MHz, CD3OD): delta = 9.12 (d, 1 H, J = 1 .6 Hz), 8.90-8.83 (m, 2H), 8.15 (dd, 1 H, J = 8.2 Hz, 5.8 Hz), 7.67 (d, 1 H, J = 15.8 Hz), 7.01 (d, 1 H, J = 15.8 Hz), 3.42-3.34 (m, 4H), 2.99 (td, 2H, J = 12.7 Hz, 2.3 Hz), 2.02-1 .94 (m, 2H), 1 .69- 1 .58 (m, 3H), 1 .50-1 .34 (m, 6H).

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, 19337-97-4, trans-3-(3-Pyridyl)acrylic acid.

Reference:
Patent; CENTRE HOSPITALIER UNIVERSITAIRE VAUDOIS CHUV; CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (CSIC); VOGEL, Pierre; DUCHOSAL, Michel; AIMABLE, Nahimana; INMACULADA, Robina; MOLLINEDO, Faustino; NENCIONI, Alessio; (105 pag.)WO2018/24907; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 52313-50-5, 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. 52313-50-5, name is Picolinimidamide. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 2-(4-methyl-2-(naphthalen-2-yl)thiazol-5-yl)-5-(methylsulfonyl)-1,3,4-oxadiazole(9) (0.09 g, 0.25 mmol) in dry DMF (5 mL), the appropriateamine, hydrazine, guanidine or carboxamidine (0.4 mmol) was added.The reaction mixture was heated at 80 C for 0.5-12 h, and then pouredon ice water (50 mL). The formed solid was extracted with ethyl acetate(10 mL). The organic layer was evaporated under reduced pressure. Theobtained crude material was then purified by column chromatography.Physical properties and spectral analysis of isolated products are listed below:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52313-50-5, its application will become more common.

Reference:
Article; Hannoun, Mohamed H.; Hagras, Mohamed; Kotb, Ahmed; El-Attar, Abdul-Aziz M.M.; Abulkhair, Hamada S.; Bioorganic Chemistry; vol. 94; (2020);,
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.139042-59-4, name is 5-Acetyl-2-bromopyridine, molecular formula is C7H6BrNO, molecular weight is 200.03, as common compound, the synthetic route is as follows.COA of Formula: C7H6BrNO

In a 50 mL round-bottomed flask under nitrogen, sodium borohydride (0.390 g, 10.31 mmol) was added portionwise on 5 min to a solution of 5-acetyl-2-bromopyridine (0.515 g, 2.57 mmol) in 2-propanol (10 mL) and water (4 mL) and the mixture was stirred at room temperature for 30 min. The mixture was then concentrated in vacuo and water was added to the concentrate. The mixture was extracted with ethyl acetate (x3) and the combined organic extract was dried over anhydrous Na2SO4 and concentrated. The obtained residue was purified on the ISCO using a 25g SILICYCLE column (elution with hexanes-EtOAc) to give the title material (0.470 g, 90%) as colorless oil. LC (Method B): 1.233 min. LCMS (APCI): calcd for C7H9BrNO [M+H]+ m/z 201.986, found 202.0. 1H NMR (400 MHz, acetone-d6): delta ppm 8.38 (d, J= 2.7 Hz, 1H) 7.71 – 7.77 (m, 1H) 7.54 (d, J= 8.2 Hz, 1H) 4.92 (q, J= 6.7 Hz, 1H) 1.43 (d, J= 6.7 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139042-59-4, 5-Acetyl-2-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; PRIESTLEY, Eldon Scott; POSY, Shoshana L.; TREMBLAY, Francois Tremblay; MARTEL, Alain; MARINIER, Anne; WO2013/163241; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1195-59-1 , The common heterocyclic compound, 1195-59-1, name is 2,6-Pyridinedimethanol, molecular formula is C7H9NO2, 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 A Preparation of 2,6-bis(chloromethyl)pyridine To 100 mL of thionyl chloride that was cooled (ice bath) was added 24 g (0.17 mol) of 2,6-bis(hydroxymethyl)pyridine. After 30 min, the reaction mixture was warmed to room temperature, then refluxed for 1.5 hrs. After cooling the reaction mixture to room temperature, the solid which formed was filtered, washed with benzene and dried in vacuo. The solid was then neutralized with saturated NaHCO3, filtered and dried to yield 23.1 g (71.5%) of the titled product as an off-white crystalline solid, mp 74.5-75.5 C., and further characterized by: 1 H NMR (CDCl3); delta 4.88 (s, 4H), 7.25-7.95 (m, 3H).

The synthetic route of 1195-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; The University of Texas; US5834456; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 15513-52-7, name is 2,6-Dimethyl-3-nitropyridine, molecular formula is C7H8N2O2, 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. Quality Control of 2,6-Dimethyl-3-nitropyridine

3-Nitro-2,6-lutidine (2.50 g, 16.5 mmol, 1 equiv.) was dissolved in 200 mL of argonpurged carbon tetrachloride. The reaction mixture was heated to 50 C under argon. AIBN (0.14 g, 0.83 mmol, 5 mol%) was added to the reaction mixture in one portion under constant stirring, followed by the addition of NBS (2.93 g, 16.5 mmol, 1 equiv.) in small portions over a period of 2 hours. The reaction mixture was further refluxed for 8 hours at constant stirring and under light irradiation. Once the reaction was complete, solvent was removed in vacuo producing a brownish residue. This residue was suspended in a mixture of methanol-dichloromethane, in which non-dissolved solids were removed by filtering through a Si02 plug (ca. 120 mL) using an eluent of methanol-dichloromethane (1:20 v/v). Fractions containing ii were combined and solvent was removed in vacuo. The resultant oil was subject to Si02 column chromatography using a mixture of ethyl acetate (gradient from 2% to 10%) in hexanes as an eluent. Fractions containing product were concentrated in vacuo producinganalytically pure ii. Yield: 0.41 g, 1.78 mmol, 11%. ?H NMR, 500 MHz (CDC13, ppm): oe =8.26 d (1H, Ar, J = 9 Hz), 7.47 d (1H, Ar, J = 9 Hz), 4.52 s (2H, CH2), 2.83 s (3H, CH3). ?3C NMR, 75 MHz (CDC13, ppm): oe = 160.46, 153.73, 144.66, 133.66, 121.61, 32.07, 23.84. ESIMS (mlz): [M+H], calculated: 231.0, found: 231.0.

With the rapid development of chemical substances, we look forward to future research findings about 15513-52-7.

Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK UNIVERSITY AT BUFFALO; HEALTH RESEARCH, INC.; MORROW, Janet, R.; TSITOVICH, Pavel, B.; DORAZIO, Sarina, J.; OLATUNDE, Abiola, O.; SNYDER, Eric, M.; SPERNYAK, Joseph, A.; BURNS, Patrick; BOND, Christopher, J.; WO2015/38943; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 14150-94-8 , The common heterocyclic compound, 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one, molecular formula is C6H5N3O5, 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.

A mixture of SP-0010418-2 (1.2 g, 5.128 mmol), 1-methyl-3,5-dinitropyridin- 2(1H)-one (1.53 g, 7.692 mmol) and 7.0 M NH3/MeOH (2.0 mL) in MeOH (8.0 mL) was stirred at 90 C for 0.5 h under microwave irridation. The residue was purified by silica gel column chromatography (using petroleum ether/EtOAc = 10:0 – 7:3) to give mixture SP0010418-162-3A and SP-0010418-162-3B (910 mg, yield: 57%). LC-MS 314 (M+H), 91%(UV2l4nm).

The synthetic route of 14150-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; F.HOFFMANN-LAROCHE LTD; YUAN, Junying; HAN, Nianhe; YI, Hua; WANG, Yuguang; YANG, Song; WONG, Jason, Christopher; WO2014/145512; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 14667-47-1, 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 14667-47-1 as follows.

2-Amino-nicotinic acid methyl ester (1.00g, 6.57 mmol) described in Preparation Example A-2 was dissolved at 0C in a mixed solution of nitric acid (0.7mL) and sulfuric acid (2.6mL), which was stirred at 0C for 40 minute and at room temperature for 19 hours, then, further stirred at 70C for 4 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution at 0C, which was extracted with ethyl acetate and tetrahydrofuran, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo. Methanol was added to the residue, the precipitated solid was filtered to obtain the title compound (459mg, 2.33mmol, 35%) as a white solid. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 3.86 (3H, s), 8.14 (1H, brs), 8.62 (1H, brs), 8.68 (1 H, d, J=2.7Hz), 9.04 (1 H, d, J=2.9Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14667-47-1, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16665-38-6, 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. 16665-38-6, name is (4-Methoxypyridin-2-yl)methanol, molecular formula is C7H9NO2, 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.

To a cooled (0 C) solution of 17 (700 mg, 5.03 mmol) in dry CH2Cl2 (4 mL) was added dropwise SOCl2 (2.2 mL, 30.8 mmol). The reaction mixture was stirred at 45 C for 3.5 hr. After removal of the solvent under reduced pressure, the residue was dissolved in sat. NaHCO3 and extracted with CHCl3. The extracts were dried over MgSO4 and concentrated under reduced pressure to give 19 (796 mg, quant.) as a red 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 16665-38-6, (4-Methoxypyridin-2-yl)methanol.

Reference:
Article; Fuchida, Hirokazu; Tabata, Shigekazu; Shindo, Naoya; Takashima, Ippei; Leng, Qiao; Hatsuyama, Yuji; Hamachi, Itaru; Ojida, Akio; Bulletin of the Chemical Society of Japan; vol. 88; 6; (2015); p. 784 – 791;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem