571189-49-6 | Pyridine-derivatives

18-Sep-21 News New learning discoveries about 571189-49-6

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. 571189-49-6, 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Application of 571189-49-6, Adding some certain compound to certain chemical reactions, such as: 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine,molecular formula is C10H16N4, 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 571189-49-6.

General procedure: Pd2(dba)3 (86.4mg, 0.09mmol) and Xant-phos (109.2mg, 0.19mmol) were added under N2 to a solution of 154 1E (290.0mg, 0.94mmol), INT-7 (228.6mg, 1.04mmol), and 152 potassium phosphate (400.5mg, 1.88mmol) in 111 1,4-dioxane (10mL). Then the mixture was reacted in the microwave at 150C for 1h. The mixture was cooled to RT, filtered, diluted with water (10mL), and extracted with DCM (10mL×3). The combined organic layers were washed with brine (30mL), dried over anhydrous Na2SO4, concentrated under a vacuum, and purified by preparative thin-layer chromatography to obtain 157 compound 1 (140.3mg; yield, 30%) as a yellow solid.

Reference:
Article; Yin, Lei; Li, Heng; Liu, Wenjian; Yao, Zhenglin; Cheng, Zhenzhen; Zhang, Huabei; Zou, Hui; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 1 – 28;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

6 Sep 2021 News The origin of a common compound about 571189-49-6

At the same time, in my other blogs, there are other synthetic methods of this type of compound,571189-49-6, 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, and friends who are interested can also refer to it.

Synthetic Route of 571189-49-6, 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. 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine. A new synthetic method of this compound is introduced below.

General procedure: The mixture of intermediate 18 (or 24a-h or 27a-g, 0.50mmol), intermediate 19 (or 28, 0.55mmol), Pd(OAc)2 (0.05mmol), X-phos (or Xantphos, 0.15mmol), Cs2CO3 (1.25mmol) and 1,4-dioxane (or 1,2-dimethoxyethane, DME) were refluxed under argon atmosphere for 1h-4h. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to produce title compounds 20a-d, 25a-h and 29a-g.

Reference:
Article; Zhang, Hao; Wang, Jin; Zhao, Hong-Yi; Yang, Xue-Yan; Lei, Hao; Xin, Minhang; Cao, Yong-Xiao; Zhang, San-Qi; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3619 – 3633;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Share a compound : 571189-49-6

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

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. 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

The origin of a common compound about 571189-49-6

Reference of 571189-49-6 ,Some common heterocyclic compound, 571189-49-6, molecular formula is C10H16N4, 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.

To Compound 50 0.060 g (0.205 mmole) was added 5-(4-methylpiperazin-1-yl)pyridin- 2-amine (35.42 mg, 0.9 eq) followed by the addition of 1,4-dioxane (3 mL). After degassing with nitrogen, Pd2dba3 (12 mg), BINAP (16 mg) and sodium tert-butoxide (24 mg) were added.The contents were then heated at 90 degrees in a CEM Discovery microwave for 3 hrs. Thereaction was then loaded onto a silica gel column and purified by eluting with DCM/MeOH (0-15%). ?HNMR (600 MHz, DMSO-d6) oe ppm 0.75 (t, J7.47 Hz, 3 H) 0.91 (d, J6.73 Hz, 3 H)1.04 – 1.20 (m, 2 H) 1.80 – 1.98 (m, 1 H) 2.77 (d, J=3.81 Hz, 3 H) 2.94 – 3.90 (m, 10 H) 4.54 -4.68 (m, 1 H) 7.06 – 7.23 (m, 2 H) 7.56 – 7.75 (m, 1 H) 7.90 – 8.12 (m, 2 H) 8.29 (s, 1 H) 9.07 (s,1 H) 10.98- 11.74(m,2H). LCMS(ESI)435(M+H).

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; BISI, John, Emerson; ROBERTS, Patrick, Joseph; SORRENTINO, Jessica, Ann; (304 pag.)WO2016/40848; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The origin of a common compound about 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

Synthetic Route of 571189-49-6 ,Some common heterocyclic compound, 571189-49-6, molecular formula is C10H16N4, 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.

General procedure: The mixture of intermediate d (0.5mmol), intermediate e (0.55mmol), Pd(OAc)2 (0.05mmol), X-phos or Xantphos (0.15mmol), Cs2CO3 (1.25mmol) and 1,4-dioxane or DME were refluxed under argon atmosphere for 1 h-4 h. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to produce title compound A or B.

Reference:
Article; Zhang, Hao; Wang, Jin; Shen, Ying; Wang, Hui-Yan; Duan, Wei-Ming; Zhao, Hong-Yi; Hei, Yuan-Yuan; Xin, Minhang; Cao, Yong-Xiao; Zhang, San-Qi; European Journal of Medicinal Chemistry; vol. 148; (2018); p. 221 – 237;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The origin of a common compound about 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

Some tips on 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

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

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 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

5-(4-Methylpiperazin-1-yl)pyridin-2-amine (35.6 mg, 0.185 mmol) was taken up in dry1 ,4-dioxane (2 mL) under argon. tert-Butyl 1 -(2-chloropyrimidin-4-yl)-2-oxo- 1,3 – diazaspiro[4.Sjdecane-3-carboxylate (4) (65 mg, 0.18 mmol) was added followed by cesiumcarbonate (0.173 g, 0.532 mmol) and rac-2,2?-bis(diphenylphosphino)-l,l?-binaphthyl (11.0 mg, 0.0177 mmol). Finally, palladium acetate (3.98 mg, 0.0177 mmol) was added and the mixture was sparged with argon for 20 mm, the flask fitted with a condenser and the reaction mixture heated at 100 C for 30 minutes. The reaction mixture was cooled to ambient temperature, filtered through a pad of Celite rinsing with ethyl acetate and the solvent wasremoved in vacuo to afford a dark yellow foam. Addition of water caused the product to precipitate. The solids were removed by filtration and washed with water. Drying under nitrogen affords 52 mg (56% yield) of the desired product 5 as a dark yellow solid.MS (ESI+) for C27H38N803 m/z 523.6 (M+H)5

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

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; GASTON, Ricky, D.; GADWOOD, Robert, C.; (177 pag.)WO2018/5533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The origin of a common compound about 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

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, 571189-49-6, 5-(4-Methylpiperazin-1-yl)pyridin-2-amine.

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. 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

4-(2-Dimethylcarbonyl-2-carbonyl-ethylamino)-2-pyrimidinecarboxylic acid (1.26 g, 1.2 eq),5-(4-Methyl-piperazin-1-yl)-piperidin-2-amino (0.8 g, 1 eq)And triethylamine (500 muL) in DMF (15 mL),Then add HBTU(1.51 g, 1.5 eq). The mixture was stirred at room temperature for 16 hours.Then EtOAc (50 mL) and saturated NaHCO3 solution(15 mL), the layers were separated and EtOAc EtOAcThe combined organic layers were dried (MgSO4).Filtration and evaporation to dryness, the residue was purified by column chromatography.0.98 g of the target compound 5 was obtained as a white solid(yield: 46%),Its nuclear magnetic resonance spectrum data is as follows:

Reference:
Patent; Jiangxi Runze Pharmaceutical Co., Ltd.; Liao Niansheng; Hu Xiande; Zhou Liming; Sui Guilan; (22 pag.)CN109568256; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Introduction of a new synthetic route about 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

Reference of 571189-49-6, Adding some certain compound to certain chemical reactions, such as: 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine,molecular formula is C10H16N4, 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 571189-49-6.

Example 39N-( 1 -MethylethyD-2- [(5 -methyl-2- { [5 -(4-methyl- 1 -piperazinyl)-2-pyridinyll amino I -4- pyrimidinvDaminolbenzamideA solution of 5 -(4-methyl- l-piperazinyl)-2-pyridinamine (0.29g, 0.00 lmol), Intermediate 3 (0.36 g, 1.0 mmol), Cs2CO3 (1.84g, 5 mmol), and XANTPHOS (0.089 g, 0.15 mmol) in dioxane was degassed for ~15 mins. To the degassed solution was added Pd(OAc)2 (0.023 g, 0.10 mmol). The reaction mixture was heated to 70 0C for 48 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined organic extracts were washed with brine and concentrated to a orange residue. The residue was dissolved in 50:50 H2O(0.1% TF A)ICH3CN, the solution was injected onto the Varian RP Cl 8 HPLC 5 to 95 40 min run. The impure product was concentrated and subjected to flash chromatography CH2Cl2 to 90:10:1 CHCl3:MeOH:NH4OH. Again impure product was collected. The impure material was dissolved in 0.5 mL of CH3CN and injected onto the Gilson RP Polaris C18 HPLC 5 to 60 H2O:CH3CN (0.1%TFA). The oily residue was dissolved in CH3CN and precipitated with Et2O (9 mg). 1H NMR (400 M Hz, CD3OD) delta 1.26 (d, J= 6.6 Hz, 6H), 2.33 (d, J= 1.0 Hz, 3H), 3.01 (s, 3H), 3.16 (m, 2H), 3.31 (m, 2H), 3.67 (m, 2H), 3.88 (m, 2H), 4.23 (m, IH), 7.18 (dd, J= 9.1, 0.5 Hz, IH), 7.33 (m, IH), 7.64 (m, IH), 7.70 (dd, J= 9.1, 3.0 Hz, IH), 7.81 (dd, J= 7.8, 1.3 Hz, IH), 7.93 (d, J= 1.3Hz, IH), 8.13 (d, J= 2.5Hz, IH), 8.72 (dd, J= 8.3, 1.3 Hz, IH). LC-MS (ES) m/z = 461 (M+H)+.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/147831; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Introduction of a new synthetic route about 5-(4-Methylpiperazin-1-yl)pyridin-2-amine

The synthetic route of 571189-49-6 has been constantly updated, and we look forward to future research findings.

Application of 571189-49-6 , The common heterocyclic compound, 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine, molecular formula is C10H16N4, 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.

Under N2 atmosphere, to a solution of 2′-chloro-2,3,5,6-tetrahydro-8’H-spiro[pyran- 4,9′-pyrazino[r,2′: l,5]pyrrolo[2,3-d]pyrimidine] (32, 50 mg, 0.18 mmol) and 5-(4- methylpiperazin-l-yl)pyridin-2-amine (52 mg, 0.27 mmol) in dioxane (4 mL) was added CS2CO3 (170 mg, 0.52 mmol), Pd(OAc)2 (8 mg, 0.04 mmol) and X-Phos (12 mg, 0.03 mmol). After stirring at 100 C for 12 h, the mixture was directly concentrated in vacuo. The resulting residue was purified by prep TLC to provide N-(5-(4-methylpiperazin-l-yl)pyridin-2-yl)- 2,3,5,6 etrahydro-8H-spiro[pyran-4,9′-pyrazino[l 2^ 1,5]pyiTolo[2,3-d]pyriiTddin]-2′-amine (COMPOUND 10, 20 mg, 0.05 mmol). MS (ESI+): m/z 433 [M + H]+; NMR (300 MHz, MeOD): delta 8.90 (s, 1H), 8.53 (s, 1H), 8.09 (d, J = 9.0 Hz, 1H), 8.03 (d, J = 3.0 Hz, 1H), 7.70 (d, J= 7.2 Hz, 1H), 7.09 (s, 1H), 4.24 (d, J= 1.7 Hz, 2H), 4.01 (dd, J= 12.3, 4.8 Hz, 2H), 3.77 (t, J = 11.8 Hz, 2H), 3.56 – 3.33 (m, 8H), 3.28 – 3.17 (m, 2H), 2.95 (s, 3H), 1.82 (d, J = 13.6 Hz, 2H).

The synthetic route of 571189-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copelnad; (156 pag.)WO2018/5863; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem