Trifluoroacetic acid → 5-Bromo-3-nitro-4-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)pyridin-2-amine

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Reaction Steps

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-(1-(pyridin-4-yl)ethyl)piperazine-1-carboxylate (1.1 eq, 1.12 mmol, 327 mg), TFA (5 mL) and CH2Cl2 (5 mL), then 5-bromo-4-chloro-3-nitropyridin-2-amine (257 mg, 1.02 mmol) in iPrOH (5 mL) and DIPEA (2 mL). Filtration and washing as previously described gave the product (265 mg, 58% for two steps) as a yellow solid; 1H-NMR (500 MHz, DMSO-d6) 1.29 (d, J=6.8 Hz, CH3), 2.46-2.56 (2 m, 4H, piperazine N(CH2)2), 3.05 (s, br, 4H, piperazine N(CH2)2), 3.53 (q, J=6.7 Hz, 1H, CH), 6.96 (s, br, 2H, NH2), 7.34 (dd, J=4.5, 1.5 Hz, 2H, pyridine H-3 & H-5), 8.14 (s, 1H, bromopyridine H-6), 8.52 (dd, J=4.4, 1.5 Hz, 2H, pyridine H-2 & H-6);

Provenance & Evidence