4-(Dimethylamino)Benzaldehyde → HCID 178436344, 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-3-nitro-4-(4-(1-(pyridin-2-yl)ethyl)piperazin-1-yl)pyridin-2-amine (100 mg, 0.24 mmol), DMF (1.5 mL), 1M Na2S2O4 (3 eq, 0.74 mmol, 0.74 mL) and 4-(N,N-dimethylamino)benzaldehyde (1.05 eq, 0.26 mmol, 38 mg). After 16 h, filtration of the precipitate, washing with cold water (1 mL) and trituration with Et2O gave the product (61 mg, 49%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 1.58 (br s, 3H, CHCH3), 2.44-2.58 (2 m, 4H, piperazine N(CH2)2), 3.01 (s, 6H, N(CH3)2), 3.72-3.90 (br s, 5H, piperazine N(CH2)2 & CHCH3), 6.83 (d, J=9.0 Hz, 2H, N,N-dimethylaminophenyl), 7.43 (br, 1H, pyridine H-5 or H-3), 7.52 (s, br, 1H, pyridine H-3 or H-5), 7.91-7.98 (m, 1H, pyridine H-4), 8.00 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 8.17 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.70 (br, 1H, pyridine H-6), 13.20 (br s, 1H, imidazo[4,5-b]pyridine NH);

Provenance & Evidence