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This was prepared using the same procedure as for 4-(6-bromo-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)-N-phenylpiperazine-1-carboxamide, but here using 5-bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amine (75 mg, 0.19 mmol), DMF (0.85 mL), ethanol (0.15 mL), 1M Na2S2O4 (3 eq, 0.57 mmol, 0.57 mL) and 2-methoxy-3-pyridinecarboxaldehyde (1.1 eq, 0.21 mmol, 0.024 mL). After 16 h, concentration in vacuo and preparation by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (41 mg, 50%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 2.61 (br s, 2H, piperazine NCH2), 2.72 (s, br, 2H, piperazine NCH2), 2.89 (s, 2H, CH2), 3.59-3.69 (m, 4H, piperazine N(CH2)2), 4.05 (s, 3H, OCH3), 7.19 (dd, J=7.5, 4.9 Hz, 1H, pyridine H-5), 7.38-7.41 (m, 1H, methoxypyridine H-5), 7.77 (dt, J=7.7, 1.8 Hz, pyridine H-4), 8.28 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.33 (dd, J=4.8, 1.8 Hz, 1H, pyridine H-6), 8.48 (d, br, J=3.4 Hz, 1H, methoxypyridine H-6), 8.53 (d, J=6.8 Hz, 1H, methoxypyridine H-4), 8.56 (s, br, 1H, pyridine H-2);

1. customThis was prepared
2. concentrationconcentration
3. customin vacuo and preparation by preparative tlc (CH2Cl2-MeOH, 95:5)