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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 (64 mg, 0.16 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.49 mmol, 0.49 mL) and tert-butyl 3-oxopropylcarbamate (prepared according to the procedure described in Tetrahedron 2003, 59, 1719) (1.1 eq, 0.18 mmol, 31 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 9:1) gave the product (31 mg, 37%) as a colourless solid; δH (500 MHz, DMSO-d6) 1.35 (s, 9H, C(CH3)3), 2.58 (s, br, 4H, piperazine N(CH2)2), 2.89 (t, J=5.5 Hz, 2H, CH2CH2NH), 3.30 (hidden by DMSO peak, 2H, CH2CH2NH), 3.57 (t, J=4.4 Hz, 4H, piperazine N(CH2)2), 3.59 (s, 2H, NCH2Ar), 6.92 (s, br, 1H, NH), 7.38 (dd, J=7.7, 4.8 Hz, 1H, pyridine H-5), 7.76 (dt, J=7.7, 1.5 Hz, 1H, pyridine H-4), 8.16 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.48 (dd, J=4.8, 1.5 Hz, 1H, pyridine H-6), 8.54 (d, J=1.5 Hz, 1H, pyridine H-2), 12.79 (s, br, 1H, imidazo[4,5-b]pyridine NH);

1. customThis was prepared
2. customprepared
3. concentrationconcentration
4. customin vacuo and purification by preparative tlc (CH2Cl2-MeOH, 9:1)