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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 (30 mg, 0.076 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.23 mmol, 0.23 mL) and 4-(2-morpholinoethoxy)benzaldehyde (1.2 eq, 0.091 mmol, 22 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 85:15) gave the product (8 mg, 19%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.62 (t, J=4.0 Hz, 4H, piperazine N(CH2)2), 2.72 (t, J=5.7 Hz, 2H, PhOCH2CH2), 3.30 (hidden by DMSO water peak, 4H, morpholine N(CH2)2), 3.59 (t, J=4.6 Hz, 4H, morpholine O(CH2)2), 3.61 (s, 2H, NCH2), 3.65 (s, br, 4H, piperazine N(CH2)2), 4.17 (q, J=5.8 Hz, PhOCH2CH2), 7.10 (d, J=8.9 Hz, 2H, phenyl H-3 & H-5), 7.39 (ddd, J=7.6, 4.8, 0.4 Hz, 1H, pyridine H-5), 7.78 (dt, J=7.8, 1.8 Hz, pyridine H-4), 8.11 (d, J=8.8 Hz, 2H, phenyl H-2 & H-6), 8.20 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.49 (dd, J=4.8, 1.7 Hz, 1H, pyridine H-6), 8.56 (d, J=1.7 Hz, 1H, pyridine H-2), 13.39 (s, br, 1H, imidazo[4,5-b]pyridine NH);

1. customThis was prepared
2. concentrationconcentration
3. customin vacuo and purification by preparative tlc (CH2Cl2-MeOH, 85:15)