4-(Dimethylamino)Benzaldehyde → HCID 178482675, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-phenylacetamide (0.052 g, 0.12 mmol), ethanol (3.5 ml), and 4-dimethylaminobenzaldehyde (0.025 g, 0.17 mmol) was added a freshly prepared aqueous solution of Na2S2O4 (1M; 0.48 ml, 0.48 mmol). The reaction mixture was heated at 70° C. for 5 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 50% dichloromethane in ethyl acetate and then 2% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as a yellow solid after trituration with diethyl ether (0.011 g, 17%); 1H-NMR (500 MHz, DMSO-d6) 2.76 (br s, 4H, piperazine N(CH2)2), 2.99 (s, 6H, N(CH3)2), 3.23 (s, 2H, NCH2CO), 3.71 (br s, 4H, piperazine N(CH2)2), 6.81 (d, J=9.15 Hz, 2H, 3,5-C6H4NMe2 or 2,6-C6H4—NMe2), 7.06 (t, J=7.52 Hz, 1H, p-ArH), 7.32 (t, J=7.52 Hz, 2H, m-ArH), 7.68 (d, J=7.52 Hz, 2H, o-ArH), 8.02 (d, J=8.90 Hz, 2H, 3,5-C6H4NMe2 or 2,6-C6H4—NMe2), 8.16 (s, 1H, imidazo[4,5-b]pyridine 5-H), 9.82 (s, 1H, CONH), 13.20 (s, 1H, imidazo[4,5-b]pyridine N—H);

Provenance & Evidence