Day: August 25, 2021

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. 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, molecular formula is C10H16N4, 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. Application In Synthesis of 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

A solution of 5-(4-methylpiperazin-1-yl)pyridin-2-amine (172 mg, 0.90 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (200 mg, 0.90 mmol) cesium carbonate (1.02 g, 3.13 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethlxanthene (77.7 mg, 0.13 mmol) in dioxane (10 ml) was flushed with argon before tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) was added and the resulting solution was heated at 90 C. for 18 h. The mixture was cooled to room temperature and diluted with dichloromethane and water. The layers were separated and the aqueous layer was extracted with dichloromethane (2*25 mL). The organic layers were combined, dried over magnesium sulfate. The resulting mixture was filtered and concentrated in vacuo. The residue was triturated with methanol and dichloromethane and filtered, washed with ether and dried to give 6-chloro-4-[5-(4-methyl-piperazin-1-yl)-pyridin-2-ylamino]-2-methyl-2H-pyridazin-3-one (223 mg, 74%) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 571189-49-6.

Reference:
Patent; Berthel, Steven Joseph; Billedeau, Roland Joseph; Brotherton-Pleiss, Christine E.; Firooznia, Fariborz; Gabriel, Stephen Deems; Han, Xiaochun; Hilgenkamp, Ramona; Jaime-Figueroa, Saul; Kocer, Buelent; Lopez-Tapia, Francisco Javier; Lou, Yan; Orzechowski, Lucja; Owens, Timothy D.; Tan, Jenny; Wovkulich, Peter Michael; US2012/40949; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63071-03-4, 2-Methoxy-6-methylpyridine, 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: C7H9NO, blongs to pyridine-derivatives compound. HPLC of Formula: C7H9NO

Example given for n = 7: An oven dried round bottom flask, equipped with magnetic stir bar was sealed under argon. To the flask, THF (10 mL) and n-BuLi (2.4 M in hexanes, 2.0 mL, 4.8 mmol) were added and cooled to 0 oC. To this flask, 2-methoxy-6-methylpyridine (0.50 mL, 4.1 mmol) was added drop wise via syringe, which resulted in a yellow color that intensified to brown over a few min. After 10 min, 1,6-dibromohexane (2.0 mL, 13 mmol) was added in one portion and the color rapidly dissipated. After an additional 2 h, the reaction was quenched upon addition of water. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo. Final purification by column chromatography (0% -15% ethyl acetate in hexanes) afforded the desired compound (397 mg, 34%) along with the dimer 1,8-bis(6-methoxypyridin-2-yl)octane (180 mg, 27%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63071-03-4, 2-Methoxy-6-methylpyridine, and friends who are interested can also refer to it.

Reference:
Article; Topczewski, Joseph J.; Lodge, Alexander M.; Yasapala, Sumana N.; Payne, Maurice K.; Keshavarzi, Pedrom M.; Quinn, Daniel M.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 21; (2013); p. 5786 – 5789;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6313-54-8, 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. 6313-54-8, name is 2-Chloroisonicotinic acid, molecular formula is C6H4ClNO2, 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 Preparation of Methyl-2-chloroisonicotinate To a solution of thionyl chloride (13.85 mL, 190.38 mmol) in toluene (50 mL) was added 2-chloropyridine-4-carboxylic acid (15 g, 95 mmol). The solution was heated to reflux for 3 hours. The resulting brown color solution was cooled to room temperature, and methanol (11.56 mL, 285.6 mmol) was added slowly dropwise. The mixture was brought to reflux for 15 minutes and became clear. The solution was then cooled to room temperature and poured into water (150 mL), basified with 50 percent sodium hydroxide and extracted with ethyl acetate (2*200 ml). The organic layer was separated and washed with brine, dried with magnesium sulfate, filtered and concentrated to yield the titled compound (11.93 g, 73percent) as a brown color solid. This was used in the next step without further purification.

According to the analysis of related databases, 6313-54-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pharmacia Corporation; US6509361; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5435-54-1 , The common heterocyclic compound, 5435-54-1, name is 3-Nitropyridin-4-ol, molecular formula is C5H4N2O3, 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.

4-Hydroxy-3-nitropyridine (10.0 g, 71.4 mmol) is added portionwise to a mechanically stirred mixture of phosphorous pentachloride (16.32 g, 78.6 mmol) and phosphorous oxychloride (16.2 mL) at 55-60 C. After the addition is complete, the temperature is raised to 130-140 C. for 4 hr. After cooling to room temperature, the phosphorous oxychloride is removed and the residue is cautiously treated with ice/water, made basic with sodium carbonate and extracted with ether. The combined extract is dried, filtered and concentrated to yield 4-chloro-3-nitropyridine (5.1 g, 45% yield) as a pale yellow solid.

The synthetic route of 5435-54-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/54631; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60290-21-3, 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. 60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine. A new synthetic method of this compound is introduced below.

To a solution of 4-chloro-lH-pyrrolo[3,2-c]pyridine (XCVI) (13.3 g, 87.2 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (XCVII) (1.59 g, 113.3 mmol, 1.3 eq) in a solution of dioxane (80 mL) and water (27 mL) was added K3PO4 (46.3 g, 218 mmol, 2.5 eq) in one portion at 25C under N2. Then Pd(dppf)Cl2 (5.1 g, 6.97 mmol, 0.08 eq) was added under N2 atmosphere. The yellow solution was heated to 90-100C and stirred for 2 h. The reaction was added into water (500 mL), and the resultant solution was extracted with EtOAc (300 mL x 3). The organic layers were washed with brine (200 mL), dried over Na2S04 and concentrated to give a residue. The residue was purified by chromatography on silica gel to give 4-(3-fluorophenyl)-lH-pyrrolo[3,2- c]pyridine (XCVIII) as a red solid (10.9 g, 51.4 mmol, 58.9% yield). NMR (DMSO-£, 400 MHz) delta ppm 6.80 (s, IH), 7.24 – 7.33 (m, IH), 7.42 (d, J=6Hz, IH), 7.52 – 7.63 (m, 2H), 7.76 (d, J=8Hz, IH), 7.87 (d, J=7.6Hz, IH), 8.28 (d, J=5.6Hz, IH), 11.71 (brs, IH); ESIMS found for C13H9FN2 mlz 213.1 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60290-21-3, 4-Chloro-1H-pyrrolo[3,2-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (265 pag.)WO2017/24010; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 944582-95-0, 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. 944582-95-0, name is 6-Fluoro-4-methylnicotinic acid. A new synthetic method of this compound is introduced below.

A round bottom flask was charged with 6-fluoro-4-methylnicotinic acid (1.13 g, 7.28 mmol, Frontier) and DCM (73 mL) to give a clear solution, Thionyl chloride (5.32 mL, 72.8 mmol) was added drop-wise and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in EtOAc (10 mL) and added drop-wise to a rapidly stirred mixture of EtOAc (40 mL) and concentrated aqueous NH4OH (36.9 ml, 947 mmol). The mixture was stirred for about 1 h, and the layers were separated. The aqueous layer was further extracted with EtOAc (50 mL) and the combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to dryness under reduced pressure to give 6-fluoro-4-methylnicotinamide (0.69 g, 61%) as white solid: LC/MS (Table 2, Method d) Rt=1.03 min; MS m/z 153 (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,944582-95-0, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; US2009/312338; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 180995-12-4 , The common heterocyclic compound, 180995-12-4, name is 2,4-Dichloronicotinonitrile, molecular formula is C6H2Cl2N2, 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.

Ethyl 6-amino-4-((1-((te/f-butoxycarbonyl)amino)propan-2-yl)amino)-1 -methyl-2- oxo-1 , 2-dihydroquinoline-3-carboxylate (from step 2; 50 mg, 0.12 mmol), 2,4- dichloronicotinonitrile (21 mg, 0.12 mmol) and DIPEA (62 uL, 0.36 mmol) were combined in a microwave vial and dissolved in NMP (1 mL). The reaction mixture was heated at 110 C under microwave irradiation for 90 min, followed by heating at 110 C in a heating block for a further 8 h. The reaction mixture was cooled to rt, and trifluoroacetic acid (183 uL, 2.39 mmol) was added and the reaction mixture was stirred at 70 C for 30 min. The reaction mixture was cooled to rt, and DIPEA (0.5 mL) was added. The reaction mixture was stirred at 70 C for 4 h. The reaction mixture was cooled to rt and partitioned between EtOAc (20 mL) and water (20 mL). The aqueous layer was extracted once with EtOAc (20 mL) and the organic extracts were combined, washed twice with brine, dried (MgS04), and concentrated in vacuo affording the title compound (62 mg, 94%) as a brown oil which was used without further purification. LCMS (Method T4); RT 2.91 min; m/z 555.211 [M+H]+.

The synthetic route of 180995-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; COLLIE, Gavin; MENICONI, Mirco; BRENNAN, Alfie; LLOYD, Matthew Garth; (222 pag.)WO2019/197842; (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. 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 1-Methyl-3,5-dinitro-1H-pyridin-2-one

Into a 50 mL sealed tube was placed tert-butyl 3-methyl-4-oxocyclohexane-1-carboxylate (2.7 g, 14.7 mmol) and 1-methyl-3,5-dinitro-1,2-dihydropyridin-2-one (2.9 g, 14.7 mmol). Added 7M ammonia in methanol (20 mL), sealed, and stirred overnight at 100 C. The mixture was cooled and concentrated. The crude product was purified by preparatory HPLC. Pure fractions were combined and concentrated to yield the title compound (1.7 g, 49%) as an oil.

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, 14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas Daniel; SKALITZKY, Donald J.; TOOGOOD, Peter L.; VANHUIS, Chad A.; (416 pag.)WO2019/200120; (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. 60832-72-6, name is Oxazolo[4,5-b]pyridin-2(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 60832-72-6

The synthesis was carried out analogously to the reaction procedure of Example I-1 using: 0.50 g (3.67 mmol) of oxazolo[4,5-b]pyridin-2(3H)-one (cf. WO 2010/135014 A1), 0.82 g (3.67 mmol) of 2-chloro-5-chloromethyl-3-fluoropyridine (DE 102006015468 A1), 1.79 g (5.51 mmol) of cesium carbonate in 50 ml of DMF, 62.5 mg of cesium iodide. [0183] This gives 32.0 mg (3.1% of theory) of 4-(6-chloro-5-fluoropyridin-3-ylmethylloxazolo[4,5-b]pyridin-2(4H)-one. [0184] LC-MS (ESI positive): m/z found: 280.0 [M++H]. [0185] C12H7ClFN3O2 calculated: 279.0. [0186] 1H NMR (600 MHz, DMF-d6) delta 5.73 (s, 2H), 6.99 (t, 1H), 7.47 (dd, 1H), 8.08 (dd, 1H), 8.16 (dd, 1H), 7.56 (d, 1H) ppm [0187] 13C with 1H decoupling (CPD) NMR (150 MHz, DMF-d6) delta 52.4 (CH2), 112.6, 113.3, 145.2, 160.7 (hetaryl-C), 138.5 (Py-CCl), 154.9 (Py-CF), 126.4, 133.3, 146.2 (Py-C), 163.1 (C?O) ppm

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, 60832-72-6, Oxazolo[4,5-b]pyridin-2(3H)-one.

Reference:
Patent; Jeschke, Peter; Schindler, Michael; Woelfel, Katharina; Ebbinghaus-Kintscher, Ulrich; Voerste, Arnd; Malsam, Olga; Losel, Peter; Goergens, Ulrich; US2014/113824; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6419-36-9, Adding some certain compound to certain chemical reactions, such as: 6419-36-9, name is 2-(Pyridin-3-yl)acetic acid hydrochloride,molecular formula is C7H8ClNO2, 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 6419-36-9.

Compound 1 was prepared according to the method of a literature reported [28]. The pyrid-3-ylacetic acid hydrochloride (0.9g, 5.2mM) and triethylamine (1.4g, 13.1mM) were dissolved in dioxane (15mL), and the mixture was stirred at room temperature for about 10min. Then 1H-indole-3-carbaldehyde (0.5g, 3.5mM) and piperidine (0.6g, 15.2mM) were added, and the resulting mixture was stirred at reflux temperature for one day. After the reaction was completed, the solution was diluted with ethyl acetate, evaporated with silica and purified by flash chromatography to give the product. Yield: 1.06g (83%). 1H NMR (400MHz, DMSO-d6) delta 11.42 (s, 1H), 8.77 (d, J=2.1Hz, 1H), 8.38 (dd, J=4.7, 1.5Hz, 1H), 8.06 (d, J=7.8Hz, 1H), 8.02 (dt, J=8.0, 1.9Hz, 1H), 7.69 (d, J=2.6Hz, 1H), 7.57 (d, J=16.6Hz, 1H), 7.45 (d, J=8.0Hz, 1H), 7.36 (dd, J=7.9, 4.7Hz, 1H), 7.21-7.17 (m, 1H), 7.16-7.10 (m, 2H). HRMS (ESI) m/z calculated for C15H12N2 [M+H]+: 221.10375, found: 221.10375.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6419-36-9, 2-(Pyridin-3-yl)acetic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hua, Shixian; Wang, Xinyi; Chen, Feihong; Gou, Shaohua; Bioorganic Chemistry; vol. 92; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem