4-(Dimethylamino)Benzaldehyde → HCID 178482683, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-methyl-N-(thiazol-2-yl)acetamide (0.035 g, 0.08 mmol), ethanol (3.5 ml), and 4-dimethylaminobenzaldehyde (0.016 g, 0.11 mmol) was added a freshly prepared aqueous solution of Na2S2O4 (1M; 0.32 ml, 0.32 mmol). The reaction mixture was heated at 70° C. for 3 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 30% to 60% ethyl acetate in dichloromethane. The title compound was obtained as a pale yellow solid after trituration with diethyl ether (0.006 g, 14%); 1H-NMR (500 MHz, DMSO-d6) 2.76 (br s, 4H, piperazine N(CH2)2), 2.99 (s, 6H, N(CH3)2), 3.66 (br s, 6H, piperazine N(CH2)2 and NCH2CO), 3.75 (s, 3H, N—CH3), 6.81 (d, J=9.2 Hz, 2H) and 8.01 (d, J=9.7 Hz, 2H) (3,5-C6H4NMe2 and 2,6-C6H4—NMe2), 7.31 (d, J=3.5 Hz, 1H, thiazole 5-H), 7.55 (d, J=3.9 Hz, 1H, thiazole-H), 8.15 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.19 (s, 1H, imidazo[4,5-b]pyridine N—H);

Provenance & Evidence