4-(Dimethylamino)Benzaldehyde → HCID 178482678, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(pyridin-3-yl)acetamide (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 5.5 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 3% methanol in ethyl acetate/dichloromethane (v/v; 8:2). The title compound was obtained as a pale yellow solid after trituration with diethyl ether (0.022 g, 34%); 1H-NMR (500 MHz, DMSO-d6) 1H-NMR (500 MHz, DMSO-d6) 2.76 (br s, 4H, piperazine N(CH2)2), 3.00 (s, 6H, N(CH3)2), 3.72 (br s, 4H, piperazine N(CH2)2), 3.27 (s, 2H, NCH2CO), 6.82 (d, J=9.07 Hz, 2H), and 8.01 (d, J=9.41 Hz, 2H) (3,5-C6H4—NMe2 and 2,6-C6H4—NMe2), 7.34 (dd, J=9.41, 4.70 Hz, 1H, pyridyl 5-H), 8.12 (d, J=8.46 Hz, 1H, pyrid-3-yl), 8.16 (s, 1H, imidazo[4,5-b]pyridine 5-H), 8.27 (d, J=4.70, 1H, pyrid-3-yl), 8.85 (s, 1H, pyridyl 2-H), 10.04 (s, 1H, CONH), 13.15 (s, 1H, imidazo[4,5-b]pyridine N—H); LC-MS (ESI, m/z): Rt=5.30 min—535, 537 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 535.1596, calculated for C25H28BrN8O (M+H)+: 535.1569.

Provenance & Evidence