Ethanol → HCID 178483865, 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 (0.050 g, 0.13 mmol, 1 eq), EtOH (2.2 mL) and DMF (0.29 mL), 4-(2-dimethylaminoethoxy)benzaldehyde (0.027 g, 0.14 mmol, 1.1 eq) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.38 mL, 0.38 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 aqueous NH3 until complete dissolution was observed. This solution was deposited on two preparative silica TLC plates and eluted with DCM/MeOH (v/v; 92:8). The title compound was obtained after trituration with diethyl ether as a pale yellow solid (0.010 g, 15%); 1H-NMR (500 Mz, DMSO-d6): 2.24 (s, 6H, NMe2), 2.66 (t, J=5.5 Hz, 2H, CH2NMe2), 2.75-2.80 (m, 4H, piperazine N(CH2)2), 3.40 (s, 2H, NCH2CO), 3.70-3.76 (m, 4H), 4.13 (t, J=5.8 Hz, 2H, CH2O), 7.10 (d, J=8.5 Hz, 2H, ArH C6H4), 7.23 (d, J=4.0 Hz, 1H) and 7.49 (d, J=3.50 Hz, 1H) (thiazole H-4, H-5), 8.04-8.11 (m, 3H, imidazo[4,5-b]pyridine 5-H and ArH C6H4), 11.88 (br s, 1H, NHCO), 13.24 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z) 3.63 min—587/589 [(M+H)+, Cl isotopic pattern].

Provenance & Evidence