Trifluoroacetic acid → 5-Bromo-4-(4-((6-methoxypyridin-3-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine

Beteiligte Stoffe

Reaktionsschritte

This was prepared using the same procedure as for 5-bromo-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amine, but here using tert-butyl 4-((6-methoxypyridin-3-yl)methyl)piperazine-1-carboxylate (1.1 eq, 0.54 mmol, 165 mg), TFA (1 mL) and CH2Cl2 (3 mL), then 5-bromo-4-chloro-3-nitropyridin-2-amine (123 mg, 0.49 mmol) in iPrOH (3.5 mL) and DIPEA (1 mL). Filtration and washing as previously described gave the product (89 mg, 40% for two steps) as a yellow solid; δH (500 MHz, DMSO-d6) 2.50 (hidden by DMSO peak, s, br, 4H, piperazine N(CH2)2), 3.05 (s, br, 4H, piperazine N(CH2)2), 3.48 (s, 2H, NCH2), 3.84 (s, 3H, OCH3), 6.80 (d, J=8.5 Hz, 1H, pyridine H-5), 6.98 (s, br, 2H, NH2), 7.66 (dd, J=8.5, 2.3 Hz, 1H, pyridine H-4), 8.07 (d, J=1.1 Hz, 1H, pyridine H-2), 8.16 (s, 1H, bromopyridine H-6); LC (Method B)-MS (ESI, m/z): Rt=2.33 min—423, 425 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 423.0777, calculated for C16H19BrN6O3 (M+H)+: 423.0780.

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