Ethanol → HCID 178432921, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-bromo-4-(4-((2-methylthiazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (0.050 g, 0.12 mmol), EtOH (2.3 mL) and DMF (0.2 mL), 4-(1H-pyrazol-1-ylmethyl)-benzaldehyde (0.025 g, 0.13 mmol) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.36 mL, 0.36 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; 96:4). The title compound was obtained after trituration with ether as a white solid (0.033 g, 49%); 1H-NMR (500 Mz, DMSO-d6): δ 2.62-2.70 (m, 7H), 3.64 (s, 2H, NCH2), 3.65-3.70 (m, 4H), 5.42 (s, 2H, NCH2), 6.30 (t, J=2.5 Hz, 1H), 7.32 (s, 1H, thiazole 5-H), 7.34 (d, J=8.0 Hz, 1H), 7.48-7.51 (m, 1H), 7.86 (d, J=2.0 Hz, 1H), 8.13 (d, J=8.0 Hz, 2H), 8.23 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.49 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z) 3.17 min—549/551 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 549.1176, calculated for C25H26N8SBr (M+H)+: 549.1185.

Provenance & Evidence