Sodium Dithionite → HCID 178488867, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-chloro-4-(4-(4-chlorobenzyl)piperazin-1-yl)-3-nitropyridin-2-amine (0.027 g, 0.07 mmol), and ethanol (3.0 ml) was added 4-methoxybenzaldehyde (0.014 g, 0.10 mmol) with the aid of ethanol (1 ml) followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.3 ml, 0.3 mmol). The reaction mixture was heated at 70° C. for 4.5 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 30% ethyl acetate in dichloromethane, and then 2% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as a white solid (0.009 g, 28%); 1H-NMR (500 MHz, DMSO-d6) 2.59 (br s, 4H, piperazine N(CH2)2), 3.56 (s, 2H, NCH2), 3.69 (br s, 4H, piperazine N(CH2)2), 3.84 (s, 3H, OCH3), 7.10 (d, J=8.86 Hz, 2H) and 8.12 (d, J=8.82 Hz, 2H) (3,5-C6H4OMe and 2,6-C6H4-Ome), 7.41 (s, 4H) (3,5-ArH and 2,6-ArH), 8.07 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.35 (s, 1H, imidazo[4,5-b]pyridine N—H);

Provenance & Evidence