1-(2-Phenoxyethyl)piperazine → 5-Chloro-3-nitro-4-[4-(2-phenoxy-ethyl)-piperazin-1-yl]-pyridin-2-ylamine

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A mixture of 1-(2-phenoxy-ethyl)-piperazine (0.047 g, 0.23 mmol), isopropanol (4.0 ml), and 2-amino-4,5-dichloro-3-nitropyridine (0.034 g, 0.16 mmol) was heated at 45° C. for 18 h. The reaction mixture was allowed to cool to room temperature, absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 10% ethyl acetate in dichloromethane, 20% ethyl acetate in dichloromethane and finally 1% methanol in ethyl acetate/dichloromethane (v/v; 1:4). The title compound was obtained as a yellow solid (0.053 g, 88%); 1H-NMR (500 Mz, DMSO-d6) 2.62 (br s, 4H, piperazine N(CH2)2), 2.76 (t, J=5.62 Hz, 2H, NCH2CH2O), 3.06 (br s, 4H, piperazine N(CH2)2), 4.09 (t, J=5.37 Hz, 2H, NCH2CH2O), 6.95 (m, 5H, 2-NH2 and o-ArH and p-ArH), 7.27 (t, J=11.20 Hz, 2H, m-ArH), 8.06 (s, 1H, 6-H); LC-MS (ESI, m/z) 3.79 min—378, 380 [(M+H)+, Cl isotopic pattern].

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