Reaction Steps
This was prepared using the same procedure as for (4-(6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)methanamine, but here using tert-butyl 4-(4-(6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)phenyl)piperazine-1-carboxylate (16 mg, 0.025 mmol), TFA (0.25 mL) and CH2Cl2 (1 mL). The same purification procedure gave the desired product (10 mg, 75%) as a pale yellow solid; δH (500 MHz, DMSO-d6) 2.50 (hidden by DMSO peak, 2H, piperazine NCH2), 2.62 (s, br, 4H, piperazine N(CH2)2), 3.00 (s, br, 2H, piperazine NCH2), 3.30 (hidden by DMSO peak, 4H, piperazine N(CH2)2), 3.61 (s, 2H, NCH2), 3.64 (s, br, 4H, piperazine N(CH2)2), 7.06 (d, J=8.9 Hz, 2H, phenyl H-3 & H-5), 7.39 (dd, J=7.7, 4.8 Hz, 1H, pyridine H-5), 7.78 (d, br, J=7.7 Hz, 1H, pyridine H-4), 8.03 (d, J=8.9 Hz, 2H, phenyl H-2 & H-6), 8.17 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.49 (dd, J=4.7, 1.4 Hz, 1H, pyridine H-6), 8.56 (s, br, 1H, pyridine H-2), 13.23 (s, br, 1H, imidazo[4,5-b]pyridine NH);
