At the same time, in my other blogs, there are other synthetic methods of this type of compound,90145-48-5, 5-Bromopyridine-2-carboxamide, and friends who are interested can also refer to it.
With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.90145-48-5, name is 5-Bromopyridine-2-carboxamide, molecular formula is C6H5BrN2O, molecular weight is 201.02, as common compound, the synthetic route is as follows.Recommanded Product: 5-Bromopyridine-2-carboxamide
Example 10 Preparation of 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvcloheylamino)ethyl)picolinamide (Compound-46) and 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvclohexylamino)ethyl)picolinamide (Compound-47)[00144] 5-Bronnopicolinannide 112 (1.29 g, 6.4 mmol) and chloral (1.25 ml_) in dioxane (10 ml_) were heated to 100 0C. The mixture was concentrated to give 5- bromo-N-(2,2,2-trichloro-1 -hydroxyethyl)picolinamide 122 (99%). [00145] A solution of 5-bromo-N-(2,2,2-thchloro-1 -hydroxyethyl)picolinamide 122 (0.83 g, 2.39 mmol) in chloroform (20 ml_) was reacted with PCI5 (0.51 g, 2.33 mmol) at 50 0C for 30 minutes. The mixture was cooled to -78 0C and 4-ethylcyclohexanamine was added (1 g, 7.5 mmol). After 1 hour, the mixture was warmed to room temperature. The reaction mixture was subjected to an aqueous work-up and the product extracted with chloroform. The organic solution was concentrated onto silica gel and the product was eluted (flash: 97:3 hexane:ether then prep-HPLC: Phenomenex Luna column (Sitheta2), 10 micron, 250×50 mm, 150 mL/minute; 3:7 hexanes:dichloromethane) to give first eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcyclohexylamino)ethyl)picolinamide (Compound-46, 106 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.26 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.6 Hz, 1 H), 8.01 (dd, J = 8.4, 2.4 Hz, 1 H), 5.56 (t, J = 9.3 Hz, 1 H), 2.96 (brs, 1 H), 1.80- 1.71 (m, 2H), 1.59-1.21 (m, 10H), 0.85 (t, J = 7.2 Hz, 3H), and second eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4-ethylcyclohexylamino)ethyl)picolinamide (Compound- 47, 166 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.30 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.9 Hz, 1 H),8.01 (dd, J = 8.4, 2.1 Hz, 1 H), 5.50 (t, J = 8.7 Hz, 1 H), 2.68-2.58 (m, 1 H), 2.16-2.07 (m, 1 H), 1.86-1.70 (m, 4H), 1.27-1.01 (m, 6H), 0.96-.087 (m, 1 H) 0.83 (t, J = 7.5 Hz, 3H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,90145-48-5, 5-Bromopyridine-2-carboxamide, and friends who are interested can also refer to it.
Reference:
Patent; ALLERGAN, INC.; NGUYEN, Phong X.; HEIDELBAUGH, Todd M.; CHOW, Ken; GARST, Michael E.; WO2011/19681; (2011); A1;,
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