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.942947-95-7, name is 2-Amino-5-bromo-4-chloro-3-nitropyridine, molecular formula is C5H3BrClN3O2, molecular weight is 252.45, as common compound, the synthetic route is as follows.HPLC of Formula: C5H3BrClN3O2
To a solution of tert-butyl 4-(2-(methyl(thiazol-2-yl)amino)-2-oxoethyl)piperazine-1-carboxylate (0.20 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid (2.0 ml). The reaction mixture was stirred at room temperature for 1.5 h, then the solvents were removed under reduced pressure to afford N-methyl-2-(piperazin-1-yl)-N-(thiazol-2-yl)acetamide as the TFA salt that was dried in vacuo. To a mixture of this material (supposedly 0.20 mmol) and isopropanol (3.8 ml) was added 2-amino-5-bromo-4-chloro-3-nitropyridine (0.050 g, 0.20 mmol) followed by diisopropylethylamine (0.126 g, 0.97 mmol). The reaction mixture was stirred at 45 C. for 20 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 20% to 40% ethyl acetate in dichloromethane. The title compound was obtained as a yellow solid (0.042 g, 46%); 1H-NMR (500 MHz, DMSO-d6) 2.69 (br s, 4H, piperazine N(CH2)2), 3.08 (br s, 4H, piperazine N(CH2)2), 3.63 (s, 2H, NCH2CO), 3.70 (s, 3H, N-CH3), 6.98 (s, 2H, NH2), 7.27 (d, J=3.6 Hz, 1H, thiazole H), 7.53 (d, J=3.6 Hz, 1H, thiazole H), 8.17 (s, 1H, 6-H);LC (Method B)-MS (ESI, m/z) Rt=2.75 min-456, 458 [(M+H)+, Br isotopic pattern].
At the same time, in my other blogs, there are other synthetic methods of this type of compound,942947-95-7, 2-Amino-5-bromo-4-chloro-3-nitropyridine, and friends who are interested can also refer to it.
Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH; US2009/247507; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem