Synthetic Route of 201937-23-7, 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. 201937-23-7, name is 6-Chloronicotinimidamide hydrochloride. A new synthetic method of this compound is introduced below.
2-(6-chloropyridin-3-yl)-N-(l-methyl-lH-pyrazol-4-yl)-4-(propan-2-yloxy)-7,8-dihydropyrido- [4,3-d]pyrimidine-6(5H)-carboxamide (K-2)A mixture of unpurified K-I (12.5 g, 42.5 mmol), 6-chloropyridine-3- carboximidamide hydrochloride (12.2 g, 54.0 mmol), and K2CO3 (17.61 g, 127 mmol) was diluted with DMF (140 ml) and treated with 2-iodopropane (10.62 ml, 106 mmol) in a 1-L round bottom flask with stirring. The reaction mixture was heated to 65 ºC and stirred for 3 h. The mixture was removed from heat and treated with 1.5 L H2O in a 3 -L Erlenmeyer flask to precipitate desired product. The mixture was stirred vigorously for 1 h and filtered through a coarse scintered glass funnel. The wet paste was transferred to a 1-L round bottom flask with toluene (300 mL) and acetone (300 mL) and concentrated in vacuo. The resulting residue was subjected to a second toluene (400 mL) azeotrope. The solids were dried under high vacuum over the weekend. The solids were suspended in 800 mL chloroform and heated to 40 ºC with stirring for 1 hr. The hazy solution was filtered through Celite, and the filtrate was concentrated in vacuo. The resulting off white foam (-12.5 g) was diluted with EtOH (1 L) and stirred at 85 ºC for 1 hr until a clear solution persisted. The solution was cooled RT and concentrated to dryness. The solids were stirred vigorously in Et2O (750 mL) for 15 min, and the mixture was filtered through a large scintered glass funnel. The solids were washed with diethyl ether (3x 350 mL), air-dried under vacuum for 10 min, and then dried under high vacuum for 24 h with routine agitation to afford the title compound (11.5, 63%) as a white solid. Data for K-2: 1H NMR (500 MHz, CDCl3) delta 9.36 (d, J= 1.7, IH), 8.61 (dd, J= 8.3, 2.2 Hz, IH), 7.75 (s, IH), 7.41 (d, J= 8.3 Hz, IH), 7.40 (s, IH), 6.40 (s, IH), 5.60 (hept, J= 6.2 Hz, IH), 4.50 (s, 2H), 3.88 (s, 3H), 3.84 (t, J= 5.6 Hz, 2H), 3.01 (t, J= 5.6 Hz, 2H), 1.46 (d, J= 6.2 Hz, 6H); HRMS m/z (M+H) 424.1561 found, 424.1535 required.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,201937-23-7, its application will become more common.
Reference:
Patent; MERCK SHARP &; DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; SCHREIER, John, D.; WO2010/138430; (2010); A1;,
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