1-((2-Methyl-1,3-thiazol-4-yl)methyl)piperazine → 5-Bromo-4-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

LC (Method B)-MS (ESI, m/z): Rt=0.50 min—198 [(M+H)+, 100%]. Half of this material (i.e. 2-methyl-4-(piperazin-1-ylmethyl)thiazole; supposedly 0.331 g, 1.68 mmol, 0.55 eq) was suspended in iPrOH (3.3 mL) and DIPEA (1.3 mL). To this solution, 5-bromo-4-chloro-3-nitropyridin-2-amine (0.390 g, 1.53 mmol, 0.45 eq) was added and the mixture heated and stirred for 17 h at 60° C. The mixture was filtered, washed with iPrOH (3×3 mL), cold H2O (3×3 mL), Et2O (2×3 mL), and dried to give the title compound (0.380 g, 55%); 1H-NMR (500 MHz, DMSO-d6): δ 2.50-2.70 (m, 7H, piperazine N(CH2)2 and Me), 3.07 (br s, 4H, piperazine N(CH2)2), 3.60 (s, 2H, NCH2), 6.98 (br s, 2H, NH2), 7.29 (s, 1H. thiazole 5-H), 8.17 (s, 1H, pyridine 6-H); LC (Method B)-MS (ESI, m/z): Rt-2.00 min—413/415 [(M+H+), Br isotopic pattern, 100%].

Provenance & Evidence