Ethanol → HCID 178521208, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide (0.060 g, 0.15 mmol, 1 eq), EtOH (2.6 mL) and DMF (0.35 mL), 4-(4-hydroxypiperidin-1-yl)benzaldehyde (0.034 g, 0.17 mmol, 1.1 eq) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.45 mL, 0.45 mmol). The reaction mixture was heated at 85° C. for 24 h, then allowed to cool to room temperature and diluted with DCM and a few drops of aq NH3 until complete dissolution was observed. This solution was deposited on two preparative silica TLC plates and eluted with DCM/MeOH (v/v; 94:6). The title compound was obtained after trituration with diethyl ether as a yellow solid (0.011 g, 13%); 1H-NMR (500 Mz, DMSO-d6): 1.40-1.50 (m, 2H), 1.77-1.87 (m, 2H), 2.60-2.92 (br s, 4H, piperazine N(CH2)2), 2.95-3.05 (m, 2H), 3.63-3.85 (m, 7H), 4.61-4.75 (br s, 1H, CHOH), 7.04 (d, J=9.0 Hz, 2H, ArH, C6H4), 7.24-7.29 (m, 1H) and 7.50 (d, J=3.5 Hz, 1H) thiazole H-4, H-5), 8.01 (d, J=8.5 Hz, 2H, ArH, C6H4), 8.07 (s, 1H, imidazo[4,5-b]pyridine 5-H); LC (Method B)-MS (ESI, m/z) 3.69 min—514/516 [(M+H)+, Cl isotopic pattern].

Provenance & Evidence