4-(Dimethylamino)Benzaldehyde → HCID 178482670, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-chloro-4-(4-(2-chloro-6-fluorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine (0.045 g, 0.11 mmol), ethanol (3.2 ml), and 4-dimethylaminobenzaldehyde (0.022 g, 0.15 mmol) was added a freshly prepared aqueous solution of Na2S2O4 (1M; 0.4 ml, 0.4 mmol). The reaction mixture was heated at 70° C. for 6 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 diethyl ether/dichloromethane (v/v; 1:1). The title compound was isolated as a pale yellow solid after trituration with diethyl ether (0.09 g, 16%); 1H-NMR (500 Mz, DMSO-d6) 2.68 (br s, 4H, piperazine N(CH2)2), 2.99 (s, 6H, N(CH3)2), 3.63 (br s, 4H, piperazine N(CH2)2), 3.70 (s, 2H, NCH2), 6.80 (d, J=8.56 Hz, 2H) and 8.00 (d, J=8.55 Hz, 2H) (3,5-C6H4—NMe2 and 2,6-C6H4—NMe2) 7.26 (t, J=9.78 Hz, 1H) and 7.40 (m, 2H) (ArH), 8.03 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.12 (s, 1H, imidazo[4,5-b]pyridine N—H);

Provenance & Evidence