Sodium Dithionite → HCID 178488880, 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 5-chloro-3-nitro-4-(4-(pyrimidin-5-ylmethyl)piperazin-1-yl)pyridin-2-amine (19 mg, 0.054 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.16 mmol, 0.16 mL) and 4-methoxybenzene carboxaldehyde (1.1 eq, 0.060 mmol, 8 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (9 mg, 38%) as a pale yellow solid; δH (500 MHz, DMSO-d6) 2.63 (s, br, 4H, piperazine N(CH2)2), 3.64 (s, 2H, CH2), 3.70 (s, br, 4H, piperazine N(CH2)2), 3.84 (s, 3H, CH3), 7.09 (d, J=8.8 Hz, 2H, methoxyphenyl H-2 & H-6), 8.08 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.12 (d, J=8.8 Hz, 2H, methoxyphenyl H-3 & H-5), 8.80 (s, 2H, pyrimidine H-4 & H-6), 9.12 (s, 1H, pyrimidine H-2), 13.32 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Provenance & Evidence