Category: 775288-71-6

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

Application of 775288-71-6, 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. 775288-71-6, name is 1-(6-Nitropyridin-3-yl)piperazine, molecular formula is C9H12N4O2, 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.

A mixture of 5-Bromo-2-nitropyridine (203 g, 1.37 mol), piperazine (153 g, 1.77 mol), tetrabutylammonium iodide (25.2 g, 0.068 mol), and potassium carbonate (207 g, 1.50 mol) in dimethyl sulfoxide (2.6 L) was stirred at 80C overnight. The resultant reaction mixture was cooled to room temperature, and the mixture was poured into water (7 L). The resultant solid was collected by filtration, and the solid was washed with dichloromethane (1 L × 2) and dried. The filtrate was extracted with chloroform (2 L × 7). The resultant organic phase was washed with water (2 L) and then with saturated brine (2 L), and the organic phase was concentrated under reduced pressure to yield solid. The resultant solid products were combined together and used for the subsequent reaction without further purification. (0173) The solid product (490 g) was dissolved in THF (2 L) and water (500 mL), and sodium hydrogen carbonate (119 g, 1.42 mol) was added to the solution. To the resultant suspension was added di-tert-butyl dicarboxylate (262 g, 1.2 mol), and the mixture was stirred at room temperature for three hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water (1 L) and extracted with dichloromethane (1 L × 3). The resultant organic phases were combined together and then washed with water (1 L). The aqueous phase was extracted with dichloromethane (300 mL). The resultant organic phases were combined together and dried over anhydrous magnesium sulfate. The solid was separated by filtration, and the filtrate was concentrated under reduced pressure. The resultant solid was suspended in ethyl acetate (2 L) and heated to 60C, and the solid was separated by filtration at 60C. The solid was dried under reduced pressure to yield the title compound (191 g, 62%) APCI-MS (M+H)+ 309.1, C14H20N4O4=308.15 1H-NMR delta(400 MHz, CDCl3) : 8.16 (d, J=9 Hz, 1H), 8.11 (d, J=3 Hz, 1H), 7.19 (dd, J=9.3 Hz, 1H), 3.64-3.61 (m, 4H), 3.45-3.42 (m, 4H), 1.47 (s, 9H)

According to the analysis of related databases, 775288-71-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teijin Pharma Limited; MIZUNO, Tsuyoshi; SHIMADA, Tomohiro; UNOKI, Gen; EBISAWA, Masaru; TAKEUCHI, Susumu; MINAMIZONO, Kunio; SASAKI, Kosuke; YOKOSAKA, Takuya; IGARASHI, Junji; MARUYAMA, Akinobu; TAKAHASHI, Hiroshi; HORIE, Kyohei; SAKAI, Yuri; (447 pag.)EP3305785; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 775288-71-6 ,Some common heterocyclic compound, 775288-71-6, molecular formula is C9H12N4O2, 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 54 (305 mg , 0.96 mmol), 69 (200 mg, 0.96 mmol) and benzotriazole-l -yl- oxy-tris-(dimethylamino)- phosphonium hexafluorophosphate reagent (637 mg, 1.44 mmol) in anhydrous DMSO (10 mL) was added DIPEA (0.67 mL, 3.84 mmol). The reaction mixture was stirred at room temperature for 12 h. The progress of the reaction mass was monitored by LCMS. The reaction mixture diluted with water (100 rriL) and the resulting mixture was extracted with ethyl acetate (2 x 100 mL). The organic layer was washed with brine (100ml), dried (Na2S04), filtered, and evaporated under vacuum. The crude product was purified by column chromatography to give 40 mg of the desired product. LC-MS: m/z calcd for C23H21N7O5S, 507.52, found: 508.0 (M+H)+. *H NMR (500 MHz, DMSO-d6): deltaEta 3.55 (2H, s, NCH2CH2N), 3.7 (2H, s, NCH2CH2N), 3.75 (2H, s, NCH2CH2N), 3.8 (5H, s, NCH2CH2N & ArOCH3), 6.74 (1H, s, SCHCH), 6.98 (2H, d, J = 10 Hz, ArCH), 7.4 (2H, d, J = 10 Hz, ArCH), 7.5 (1H, d, J = 10 Hz, ArCH), 7.56 (2H, s, NH2), 8.18 (1H, d, J = 10 Hz, ArCH) and 8.26 (1H, d, J = 5 Hz, ArCH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,775288-71-6, its application will become more common.

Reference:
Patent; GE HEALTHCARE LIMITED; MEDI-PHYSICS, INC.; JONES, Clare; GLASER, Matthias Eberhard; WYNN, Duncan; NAIRNE, James; MOKKAPATI, Umamaheshwar P.; NEWINGTON, Ian, Martin; RANGASWAMY, Chitralekha; JOSE, Jinto; JOHANSSON, Saga; WO2013/90497; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem