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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-chloro-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amine (12.5 mg, 0.036 mmol), DMF (0.10 mL), ethanol (0.70 mL), 1M Na2S2O4 (3 eq, 0.11 mmol, 0.11 mL) and 4-(1H-pyrazol-1-ylmethyl)benzaldehyde (1.1 eq, 0.039 mmol, 8 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 9:1) gave the product (5 mg, 29%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.60 (s, br, 4H, piperazine N(CH2)2), 3.61 (s, 2H, NCH2), 3.70 (s, br, 4H, piperazine N(CH2)2), 5.41 (s, br, 2H, PhCH2), 6.30 (t, J=1.9 Hz, pyrazole H-4), 7.34 (d, J=8.4 Hz, 2H, phenyl H-3 & H-5), 7.37 (dd, J=7.6, 4.6 Hz, 1H, pyridine H-5), 7.49 (s, br, 1H, pyrazole H-3 or H-5), 7.78 (d, br, J=7.5 Hz, 1H, pyridine H-4), 7.86 (d, J=2.0 Hz, 1H, pyrazole H-3 or H-5), 8.11 (d, J=8.5 Hz, 2H, phenyl H-2 & H-6), 8.12 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.49 (dd, J=4.7 Hz, 1H, pyridine H-6), 8.56 (s, br, 1H, pyridine H-2), 13.47 (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, 9:1)