Pyridine-derivatives

Synthetic Route of 571189-16-7, 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 571189-16-7, name is tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 2 tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate In a nitrogen atmosphere, to a solution of tert-butyl 4-(6-nitro-3-pyridine) piperazine-1-carboxylate (28.00 g, 90.81 mmol, 1.00 equivalent) in methanol (600 mL) was added palladium on carbon (6%, 1.7 g). The suspension was evacuated and filled with hydrogen several times. The solution was stirred at 50C in a hydrogen atmosphere (50psi) for 18 hours. TLC (dichloromethane: methanol = 10: 1) showed that the starting material reacted completely. The suspension was filtered, and the filtrate was dried using a rotary vacuum dryer to give the title compound (24.13 g, 86.69 mmol. 95.46% yield) as a purple solid. 1H NMR (400 MHz, CDCl3) delta 7.78 (d, J = 2.64 Hz, 1H) 7.18 (dd, J = 8.78, 2.89 Hz, 1H) 6.50 (d, J = 8.78 Hz, 1H) 4.21 (brs, 2H) 3.60-3.54 (m, 4H) 3.00-2.92 (m, 4H) 1.48 (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 571189-16-7, tert-Butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; DING, Charles Z.; CHEN, Shuhui; ZHAO, Baoping; XU, Zhaobing; LIU, Yingchun; LIN, Ruibin; WANG, Fei; LI, Jian; (101 pag.)EP3269715; (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.1052714-46-1, name is 6-Bromo-5-fluoropicolinic acid, molecular formula is C6H3BrFNO2, molecular weight is 219.9959, as common compound, the synthetic route is as follows.Recommanded Product: 1052714-46-1

[0273] 6-Bromo-5-fluoro-pyridine-2-carboxylic acid (24.0 g, 109 mmol) was dissolved in a mixture of EtOH (400mL) and cone. H2SO4 (17.5 mL, 328 mmol). The mixture was heated at 90 C for 2.5 h. After cooling to 0 C, a solution of 3.50 M NaOH (90.0 mL, 315 mmol) was slowly added with vigorous stirring (pH adjusted to approx. 4), followed by a sat. solution of NaHC03 until pH was approx. 8. The slurry was filtered through a pad of Celite, and the filtrate was concentrated under reduced pressure. The residue was suspended in cold water (300 mL) and stirred at 0 C for 5 m. The mixture was filtered, washing with water, and the solid was dried under vacuum to provide the title compound as a solid (20.4 g, 75%). XH NMR (500 MHz, (0777) CDC13) delta 8.12 (dd, J = 8.3, 3.6 Hz, 1H), 7.53 (dd, J = 8.3, 7.0 Hz, 1H), 4.47 (q, J = 7.1 Hz, 2H), 1.43 (t, J = 7.1 Hz, 3H). LC-MS (Method C): m/z (ES+), [M+H]+ = 247.8. HPLC tR = 1.74 m.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1052714-46-1, 6-Bromo-5-fluoropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; CUMMING, John, Graham; WU, Frank, Xinhe; EDMAN, Karl, Henrik; CHEN, Hongming; BROWN, Dean, Gordon; BURLI, Roland, Werner; JOHNSTONE, Shawn, Donald; BROWN, Giles, Albert; TEHAN, Benjamin, Gerald; TEOBALD, Barry, John; CONGREVE, Miles, Stuart; (187 pag.)WO2017/194716; (2017); A1;,
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Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76469-41-5, 2,3,5-Trifluoropyridine, 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, 76469-41-5, blongs to pyridine-derivatives compound. Formula: C5H2F3N

A mixture of 2, 3, 5-trifluoropyridine (5.0 g, 37.6 mmol, 1.0 equiv) and 1, 3-dimethyl propanedioate (7.4 g, 56.0 mmol, 1.5 equiv) and Cs 2CO 3 (24.5 g, 75.2 mmol, 2.0 equiv) in DMSO (100.0 mL) was stirred for 10 hours at 100C under nitrogen atmosphere. The resulting mixture was extracted with EtOAc (4 x 50 mL). The combined organic layers were washed with H2O (3 x 50 mL), dried over anhydrous Na 2SO 4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (20: 1) to afford 1, 3-dimethyl 2- (3, 5-difluoropyridin-2-yl) propanedioate (8.1 g, 79.13%) as a yellow oil. LCMS: m/z (ESI), [M+H] + = 246.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76469-41-5, its application will become more common.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; ZENG, Qingbei; QI, Changhe; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (206 pag.)WO2020/52631; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1620-77-5, 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.1620-77-5, name is 5-Methylpicolinonitrile, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.

[5-METHYL-PYRIDINE-2-CARBONITRILE] (3.34 g, 28.3 mmol) was mixed with [18] percent HCl (12 ml) and ethanol [(6ML)] and refluxed for 40 h. The reaction mixture was concentrated by rotavapor and the residue was triturated with acetone to give off-white solid 5-methyl-pyridine-2- carboxylic acid hydrochloride. This solid was hydrogenated with [PT02] in ethanol for 2 days until no W active material left. The reaction mixture was filtered, concentrated by vacuum. The residue was triturated with acetone to give 5.3 g of cis and trans 5-methyl- piperidine-2-carboxylic acid hydrochloride as white solid (quantitative).

Statistics shows that 1620-77-5 is playing an increasingly important role. we look forward to future research findings about 5-Methylpicolinonitrile.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14902; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 500-22-1, 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 500-22-1 as follows.

General procedure: In a round-bottomed flask equipped with a condenser and a magnetic stirrer, a mixture of aldehyde (1 mmol), 1,2-phenylenediamine (1 mmol) and Cu(II)-TDnSiO2 (10 mg, containing 0.0034 mmol Cu(II)) in EtOAc (2 mL) was stirred at 50 C. The progress of the reaction was monitored by TLC (eluent: n-hexane/EtOAc, 2:1). After completion of the reaction, the mixture was cooled to room temperature and EtOAc/EtOH (3:2, 15 mL) was added. The catalyst was separated by filtration and washed with EtOAc (10 mL). The filtrate was evaporated and the crude product was purified by recrystallization from EtOAc or EtOH to afford the pure product

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,500-22-1, its application will become more common.

Reference:
Article; Nasr-Esfahani, Mahboobeh; Mohammadpoor-Baltork, Iraj; Khosropour, Ahmad Reza; Moghadam, Majid; Mirkhani, Valiollah; Tangestaninejad, Shahram; Journal of Molecular Catalysis A: Chemical; vol. 379; (2013); p. 243 – 254;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 775288-71-6, 1-(6-Nitropyridin-3-yl)piperazine, 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, name: 1-(6-Nitropyridin-3-yl)piperazine, blongs to pyridine-derivatives compound. name: 1-(6-Nitropyridin-3-yl)piperazine

General procedure: A mixture of compounds 8c-8e (26.0 mmol) in acetic acid(10 mL) and methyl alcohol (40 mL) was refluxed, iron (78.0 mmol)was added. The reaction mixture was heated at 60 C for 2 h. Thereaction mixture was poured into saturated aqueous sodium carbonate(100 mL) and extracted with ethyl acetate (3 x 50 mL), thendried over sodium sulfate, filtered and concentrated. The crudeproduct was purified via column chromatography to afford compounds9c-9e.4.1.11.1. 5-(piperazin-1-yl)pyridin-2-amine (9c). White solid. Yield:68%; 1H NMR (DMSO-d6, 400 MHz) delta: 7.62 (d, J = 2.7 Hz, 1H, Pyr-H),7.17 (dd, J = 8.9, 3.0 Hz, 1H, Pyr-H), 6.40 (d, J = 8.8 Hz, 1H, Pyr-H),5.44 (s, 2H, -NH2), 3.43 (t, J = 4.0 Hz, 4H, Pyr-NCH2CH2N), 2.85 (t,J = 4.0 Hz, 4H, Pyr-NCH2CH2N). 13C NMR (DMSO-d6, 100 MHz):delta 163.0, 162.6, 149.4, 146.9, 133.7, 122.1, 120.3, 43.4, 42.6; HRMS(ESI): calcd for C9H14N4O, [(M+H)+], 179.1297, found 179.1285.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,775288-71-6, 1-(6-Nitropyridin-3-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Article; Zhao, Hui; Hu, Xiaoxia; Cao, Kai; Zhang, Yue; Zhao, Kuantao; Tang, Chunlei; Feng, Bainian; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 935 – 945;,
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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-Chloro-4-(pyridin-2-ylmethoxy)aniline

To a 4-Chloro-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluorene-7-carboxylic acid tert-butyl ester (3.08 g, 9.40 mmol, 1.05 equiv) in 40 mL of isopropyl alcohol solution was added 3-Chloro-4-(pyridin-2-ylmethoxy)phenylamine (2.10 g, 9.0 mmol, 1 equiv) at rt. 4 N HCl in dioxane (0.1 mL) was added to the reaction mixture to accelerate the reaction. The reaction mixture was heated at 80 C. for 16 h. The mixture was allowed to cool to rt then filtered and washed with IPA (50 mL). DCM (100 mL) and sat. sodium bicarbonate (100 mL) were added to the solid. The mixture was stirred at rt for 1 h before separated the layers. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield 4.50 g of crude material. The crude material was purified by flash chromatography (50% THF/DCM) to yield a light yellow (3.60 g, 6.87 mmol, 76%) as product. 1H-NMR (DMSO-d6) delta 9.32 (broad s, 1H), 8.67 (d, J=4.0 Hz, 1H), 8.40 (s, 1H), 8.27 (s, 1H), 8.05 (t, 1H), 7.79 (d, J=2.7 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.53 (t, 1H), 7.24 (d, J=8.9 Hz, 1H), 5.35 (s, 2H), 4.66 (s, 2H), 3.66 (t, 2H), 3.19 (t, 2H), 1.43 (s, 9H); LCMS RT=3.39 min, [M+H]+=524.0.

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, 524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/298297; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 272-52-6 ,Some common heterocyclic compound, 272-52-6, molecular formula is C6H5N3, 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.

Into a vessel was placed a solution comprising 1.0 g of lH-pyrazolo[4,3- b]pyridine (Exp-l-gl, 8.4 mmol) in 12 mL of MeOH/H20 (1 : 1, vol). Into the solution was added dropwise a solution of Br2 ( 1.6 g, 10 mmol) in MeOH/H20 (1 : 1, 5 mL) maintaining the solution temperature at 0 C during the addition. The reaction mixture thus prepared was stirred at this temperature for 40 min. The resulting precipitate was collected by filtration and the filter cake thus obtained was neutralized with saturated Na2C03 solution. The neutralized precipitate was filtered, washed with water and dried in vacuum. The crude product thus obtained (Exp-l-g2,1.2 g, 71 %) was used for the next step directly without purification. The identity of the product was verified by proton NMR in accordance with the procedures set forth above. 1HNMR: (400 MHz, DMSO) delta 13.66 (br, 1H), 8.55 (d, 1H, J = 4.0 Hz), 8.03 (dd, 1H, J = 8.8 Hz, 1.2 Hz), 7.42-7.45 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,272-52-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; JONES, Philip; LEI, Zhiyu; LIU, Fuqing; LUO, Yunfu; DONG, Jingchao; SOLL, Richard; WO2013/63100; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 139022-27-8, 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 139022-27-8 as follows.

Example 166-fluoro-3-iodo-imidazo^ ,2-alpha]pydine (29)As shown in Fig. 5, 6-Fluoro-3-iodo-imidazo[1 ,2-alpha]pyridine (29) was prepared according to a literature procedure (Enguehard et al., J. Org. Chem. 65: 6572-6575 (2000), incorporated herein by reference in its entirety). N-iodosuccinimide (9.2g, 40.8 mmol) was added to a solution of 6-fluoro-imidazo[1 ,2-alpha]pyridine 26 (Example 15) (7.6g, 40.8 mmol) in dry acetonitrile (100 ml.) at O0C. The reaction was warmed to room temperature and then stirred for 12 hours. The mixture was filtered and the cake washed with acetonitrile and water and dried under high vacuum to afford 6-fluoro-3-iodo-imidazo[1 ,2-alpha]pyridine 29 off white solid. 8.5 g, 88% yield.1H NMR (300 MHz, CDCI3, 297K) delta 7.14 (td, J = 2.1 , 7.8 Hz, 1 H), 7.59 (dd, J = 5.1 , 9.9 Hz, 1 H), 7.72 (s, 1 H), 8.07 (distorted t, J = 3.0 Hz, 1 H).ESI MS (MeOH) calcd for C7H4FIN2 262.03, found m/z (M++1 ) 263.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,139022-27-8, its application will become more common.

Reference:
Patent; ISIS INNOVATION LTD.; EBETINO, Frank, Hallock; MAZUR, Adam; LUNDY, Mark, Walden; RUSSELL, Robert, Graham Goodwin; WO2010/33978; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1289093-31-7, 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 1289093-31-7 as follows.

Preparation 14: methyl 1 -i5-chloro-6-isobutoxypyridin-3-yl)-3-cvclopropyl-1 H- indazole-5-carboxylate; A mixture of methyl 3-cyclopropyl-1 H-indazole-5-carboxylate [preparation 9] (100mg, 0.396mmol), Cul (7.6mg, 0.40mmol), K3P04 (168mg, 0.792mmol), and 5-bromo-3- chloro-2-isobutoxy-pyridine [preparation 30] (105mg, 0.396mmol) was added to a septum sealed reaction vial and degassed. A solution of trans-N, N’- dimethylcyclohexane-1 ,2-diamine in toluene (2ml) was added. The mixture was degassed and filled with nitrogen three times, then stirred at 1 10C for 4 days. The mixture was allowed to cool and then partitioned between water (5ml) and DCM (5ml). The DCM phase was separated and the aqueous extracted with further DCM (5ml). The extracts were combined and evaporated onto silica. Purification by column chromatography (ISCO Companion, silica 12g, eluted with a gradient of heptane to 40% EtOAc in heptane) gave the title compound as clear oil (100.4mg).1 H NMR (400 MHz, CDCI3) delta ppm 1 .07 (d, 6H), 1 .19-1 .12 (m, 4H), 2.18 (septuplet, 1 H), 2.27-2.34 (m, 1 H), 3.97 (s, 3H), 4.21 (d, 2H), 7.55 (dd, 1 H), 7.98 (d, 1 H), 8.09 (dd, 1 H), 8.35 (d, 1 H), 8.58 (dd, 1 H).LCMS (Method A5) Rt 1 .83 min, MS m/z 400 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1289093-31-7, its application will become more common.

Reference:
Patent; PFIZER LIMITED; BELL, Andrew Simon; DE GROOT, Marcel John; LEWTHWAITE, Russell Andrew; MARSH, Ian Roger; SCIAMMETTA, Nunzio; STORER, Robert Ian; SWAIN, Nigel Alan; WO2012/95781; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem