Sodium Dithionite → HCID 178488876, 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-bromo-4-(4-((3,5-dimethylisoxazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (20 mg, 0.049 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.14 mmol, 0.14 mL) and 4-methoxybenzene carboxaldehyde (1.1 eq, 0.053 mmol, 7 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (10 mg, 42%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.26 (s, 3H, CH3), 2.39 (s, 3H, CH3), 2.63 (t, J=4.6 Hz, 4H, piperazine N(CH2)2), 3.40 (s, 2H, CH2), 3.72 (s, br, 4H, piperazine N(CH2)2), 3.88 (s, 3H, OCH3), 7.08 (d, J=8.8 Hz, 2H, methoxyphenyl H-2 & H-6), 8.12 (d, J=8.7 Hz, 2H, methoxyphenyl H-3 & H-5), 8.21 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.03 (s, br, 1H, imidazo[4,5-b]pyridine NH); LC (Method B)-MS (ESI, m/z): Rt=3.29 min—497, 499 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 497.1301, calculated for C23H25BrN6O2 (M+H)+: 497.1301.

Provenance & Evidence