Category: pyridine-derivatives

Electric Literature of 1008-91-9, 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 1008-91-9 as follows.

General procedure: Piperazine derivatives 1-3 are known.10 Piperazine derivatives 4-14 were synthesized from the commercially available appropriate monoalkylated piperazines (1.44 mmol) and 2-nitro-1H-imidazolyl-propylbromide or 3-nitro-1H-1,2,4-triazolylpropylbromide (1.485 mmol)30 in the presence of potassium carbonate (13.24 mmol) in dry acetonitrile (25 mL) as described before.10 The reaction mixture was stirred under a nitrogen atmosphere at room temperature for 48 h, then filtered to remove the inorganic salts. The organic filtrate was evaporated and the residue extracted from water-chloroform. The organic layer was separated and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated and the residue purified by preparative TLC on alumina plates with ethyl acetate:petroleum ether mixture. The desired product was dissolved in ethyl acetate and converted to its HCl salt by treating with HCl gas in dry ether (1 M solution)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1008-91-9, its application will become more common.

Reference:
Article; Papadopoulou, Maria V.; Bloomer, William D.; Rosenzweig, Howard S.; Kaiser, Marcel; Chatelain, Eric; Ioset, Jean-Robert; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6600 – 6607;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 677728-92-6, 2-Fluoropyridine-5-carbaldehyde, 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, 677728-92-6, blongs to pyridine-derivatives compound. Quality Control of 2-Fluoropyridine-5-carbaldehyde

Intermediate 61 : ethyl trans-4-{[l-(5-formylpyridin-2-yl)piperidin-4- ylloxyl cyclohexanecarboxylaEthyl trans-4-(piperidin-4-yloxy)cyclohexanecarboxylate (260 mg, 1.02 mmol) in DMSO (3 ml) was added 2-fluoro-5-formypyridine (166 mg, 1.32 mmol), and sodium bicarbonate (855 mg, 10.2 mmol). The mixture was heated at 110 C under N2 for 2 hours. The reaction was cooled to RT, quenched with water, and extracted with ethyl acetate (2X40 ml). Dried over MgS04, filtered and concentrated. The residue was purified by preparative TLC (40%>EtOAc/Hexane) to give the title compound as a white solid. LC-MS (ES, m/z): C20H28N2O4: 360; Found: 361 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; DE VITA, Robert, J.; HONG, QingMei; LAI, Zhong; DYKSTRA, Kevin, D.; YU, Yang; LIU, Jian; SPERBECK, Donald; JIAN, Tianying; GUIADEEN, Deodial; XU-QIANG YANG, Ginger; WU, Zhicai; HE, Shuwen; TING, Pauline, C.; ASLANIAN, Robert; KUETHE, Jeffrey, T.; BALKOVEC, James, M.; KUANG, Rongze; ZHOU, Gang; WU, Heping; WO2012/164071; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 31872-62-5, 4-Methoxy-3-nitropyridine, 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: 4-Methoxy-3-nitropyridine, blongs to pyridine-derivatives compound. Recommanded Product: 4-Methoxy-3-nitropyridine

A solution consisting of 4-methoxy-3-nitropyridine (15.0 g, 97.3 mmol) with ethyl amine (46.5 mL of 70% aqueous solution, 584 mmol) in ethanol (30 mL) was stirred at 85 C in a sealed flask for 2 h. Removal of all volatiles in vacuo afforded the title compound (16.2 g, 99 %). MS: (M+H) + = m/z 168.

The synthetic route of 31872-62-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/46678; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15513-48-1, 4-Chloro-2,6-dimethyl-3-nitropyridine, 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 15513-48-1, blongs to pyridine-derivatives compound. Product Details of 15513-48-1

(c) 4-(4-Cyanophenyl)amino-2,6-dimethyl-3-nitropyridine A solution of 4-chloro-2,6-dimethyl-3-nitropyridine (9.80 g, 52.5 mmol) and 4-aminobenzonitrile (6.20 g, 52.5 mmol) in ethanol (160 ml) was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (200 ml), and washed with saturated aqueous sodium bicarbonate (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give a gum which was crystallized by adding ether (100 ml) and sonicating for 5 minutes.

The synthetic route of 15513-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4935430; (1990); A;,
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. 77992-44-0, name is (5-Bromopyridin-2-yl)hydrazine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 77992-44-0

General procedure: A mixture of 2-hydrazinylpyridine (0.5 mmol), imidazolium chloride (0.05 mmol) in DMF (2.0 mL) was stirred at 153 for 3-16 hours. The reaction was monitored by TLC. Upon completion, DMF was removed by rotary evaporator and the residue was applied for purification by flash column chromatography on silica gel to afford the desired product.

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, 77992-44-0, (5-Bromopyridin-2-yl)hydrazine.

Reference:
Article; Liu, Lingfeng; Qiao, Chunhua; Shen, Bei; Xu, Yiwen; Tetrahedron Letters; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1452-63-7, 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 1452-63-7, name is Picolinohydrazide. This compound has unique chemical properties. The synthetic route is as follows.

N-picolinoyl-N0-benzothioylhydrazide (Hpbth) was prepared byadding a methanol solution of carboxymethyl dithiobenzoate(2.12 g, 10 mmol) dropwise to 1 N NaOH solution of picolinic acidhydrazide (1.37 g, 10 mmol). The reaction mixture was stirred continuouslyfor 1 h and acidified with dil. acetic acid. The precipitateobtained was filtered off, washed with water, dried under reducedpressure and recrystallized from a mixture of MeOHACHCl3 (50:50v/v) [16]. Yield: 75%; m.p. 184 C. Found: C, 60.73; H, 4.31; N,16.30; S, 12.47%. Calc. for C13H11N3SO (257.31): C, 60.70; H, 4.28;N, 16.33; S, 12.44%. IR (cm1, KBr): m(NAH) 3236; m(CO) 1661;m(NAN) 1075; m(CS) 921. 1H NMR (DMSO-d6; d ppm): 10.63,10.05 (s,2H, NH), 8.68 (C1H), 7.90 (C2H), 7.92 (C3H), 8.044 (C4H),7.65 (C9H), 7.36 (C10H), 7.34 (C11H), 7.22 (C12H), 7.50 (C13H),13C NMR (DMSO-d6; d ppm): 190.71 (CS), 163.07 (CO), 147.53(C1), 131.17 (C2), 137.53 (C3), 131.72 (C4), 149.08 (C5), 138.05(C8), 129.16 (C9, C13), 127.97 (C10, C12), 131.06 (C11).

According to the analysis of related databases, 1452-63-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kushawaha; Dani; Bharty; Chaudhari; Sharma; Kharwar; Singh; Journal of Molecular Structure; vol. 1063; 1; (2014); p. 60 – 69;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 183741-80-2, tert-Butyl (6-methoxypyridin-3-yl)carbamate, 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, 183741-80-2, blongs to pyridine-derivatives compound. Formula: C11H16N2O3

[0614] Procedure: To a stirred solution of tert-butyl (6-methoxypyridin-3-yl)carbamate (7 g, 31.231 mmol) and tetramethylethylenediamine (14.05 mL , 93.640 mmol) in ether (140 mL) was added n-BuLi (46.82 mL, 3 eq, 2M solution in cyclohexane) at -78 C and the mixture was stirred at-10 C for 3 h. After re-cooling to- 78 C, dry carbon dioxide gas was bubbled and stirred for 5 min. The resulting suspension was allowed to room temperature and diluted with water. Organic layer separated and washed with dil. ammonium hydroxide solution. The combined aq. layer was acidified to pH 6 with dil. HCl. The resulting precipitate was filtered, dried under vacuum to afford 5-((tert-butoxycarbonyl)amino)-2-methoxyisonicotinic acid as off white solid (7.2 g, 85.99 %).1HNMR (400 MHz, DMSO-d6): delta 9.37 (bs, 1H), 8.67 (s, 1H), 7.11-(s, 1H), 3.84 (s, 3H), 1.44 (s, 9H). LC-MS (ES) m/z = 269.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,183741-80-2, its application will become more common.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 78686-79-0, Adding some certain compound to certain chemical reactions, such as: 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate,molecular formula is C7H5BrClNO2, 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 78686-79-0.

To a mixture of NaBH4 (5.8 g, 152. 6 mmol, 4 eq) and anhydrous CaCl2 (16.9 g, 152. 6 mmol) in dry DCM (100 mL) at 0C, was added slowly methyl 5-bromo-2-chloronicotinate (9.5 g, 38.15 mmol). The resulting mixture was stirred at room temperature for 12h. Water was added to the reaction mixture at 0C. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo, to afford 6.8 g (crude) of (5-bromo-2-chloropyridin-3- yl)methanol, which was used in the next step without further purification. LCMS [M+H]+ 223.1.

According to the analysis of related databases, 78686-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2011/103202; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 103041-38-9, 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 103041-38-9, name is Ethyl 3-(pyridin-2-ylamino)propanoate. This compound has unique chemical properties. The synthetic route is as follows.

c) Ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)aminolpropanoate hydrochloride [Show Image] 50 g (0.25 mol) of 4-(methylamino)-3-nitrobenzoic acid as obtained in step (a) were suspended in a mixture of 459.2 g of thionyl chloride and 3 mL of N,N-dimethylformamide. The mixture was stirred at reflux temperature for 45 minutes. Excess thionyl chloride was removed by vacuum distillation. The residue was dissolved in 300 mL of toluene, which was subsequently removed by vacuum distillation to remove completely any residual thionyl chloride. The brownish crystalline residue obtained was dissolved in 280 mL of tetrahydrofuran at 60C. At this point, 35.1 g of triethylamine were added to the solution. Then, a solution of 45 g (0.23 mol) of ethyl 3-(2-pyridylamino)propanoate as obtained in step (b) in 95 mL of tetrahydrofuran was added dropwise over the reaction mixture, keeping the temperature at about 30C. The resulting mixture was stirred overnight at room temperature. Solvent was removed by vacuum distillation, and the residue was dissolved in 1 L of dichloromethane. The resulting solution was washed with 500 mL of water, 500 mL of 2M hydrochloric acid, 500 mL of saturated sodium bicarbonate and 500 mL of water. The organic phase was dried with anhydrous sodium sulfate and concentrated under vacuum. The residue was dissolved with 600 mL of ethyl acetate, and dry hydrogen chloride was bubbled into the solution until precipitation was completed. The solid was isolated by filtration and dried to obtain 63 g of the title compound, which was recrystallized in a mixture of 450 mL of ethanol and 50 mL of acetonitrile at reflux temperature. After cooling to 10C, solid was isolated by filtration and dried to yield 44.7 g of ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate hydrochloride as a yellow solid. Yield: 47.2 %. Purity (HPLC, method 1): 97.6 %.

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 103041-38-9, Ethyl 3-(pyridin-2-ylamino)propanoate.

Reference:
Patent; Medichem, S.A.; EP2522662; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 101990-73-2, 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. 101990-73-2, name is 2-Chloro-4-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below.

Preparation of ethyl 5~rr(2-chloropyridin-4-yl)methyll(formyl)aminol-l- methyl- 1 H-pyrazole-4-carboxylateA solution of crude ethyl 5-(formylamino)-l -methyl- 1 H-pyrazole-4-carboxylate (3.0Og, 15.21mmol) from step 1 in dichloromethane (30ml) was treated with diazabicyclo(5.4.0)undec-7-ene (3.41ml, 22.82mmol) and allowed to stir at room temperature for 30 minutes. 2-Chloro-4-chloromethylpyridine (4.93g, 30.43mmol) was added, and the reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was then diluted with DCM and washed with concentrated NaHCO3 solution, followed by water, then brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was washed with ether, and the ether washings were concentrated and triturated with hexanes. The residue was again concentrated yielding 3.93g (80.1%) product as a thin oil.1R NMR (300 MHz, CD3CN) ? 8.30 (d, IH), 8.23 (s, IH), 7.85 (s, IH), 7.33 (s, IH), 7.22 (d, IH), 4.80 (bs, 2H), 4.17 (q, 2H), 3.67 (s, 3H), 1.23 (t, 3H); ES-MS m/z 323.1 [M+H]+, HPLC RT (min) 2.31.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,101990-73-2, 2-Chloro-4-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/133006; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem