Sodium Dithionite → HCID 178488864, compound

Participants

Reaction Steps

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 4-(4-(benzo[d][1,3]dioxol-4-ylmethyl)piperazin-1-yl)-5-bromo-3-nitropyridin-2-amine (30 mg, 0.068 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.21 mmol, 0.21 mL) and 4-methoxybenzene carboxaldehyde (1.1 eq, 0.075 mmol, 10 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (22 mg, 63%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.63 (s, br, 4H, piperazine N(CH2)2), 3.55 (s, 2H, NCH2), 3.65 (t, J=4.3 Hz, 4H, piperazine N(CH2)2), 3.84 (s, 3H, OCH3), 6.02 (s, 2H, OCH2), 6.83 (d, J=4.2 Hz, 2H, benzo[d][1,3]dioxyl H-4 & H-6), 6.90 (app. q, J=4.4 Hz, 1H, benzo[d][1,3]dioxyl H-5), 7.09 (d, J=8.9 Hz, 2H, methoxyphenyl H-2 & H-6), 8.14 (d, J=8.9 Hz, 2H, methoxyphenyl H-3 & H-5), 8.20 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.34 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Provenance & Evidence