Ethanol → HCID 178432925, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

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-yl)-benzaldehyde (0.023 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 to give the title compound as a off-white solid (0.016 g, 25%); 1H-NMR (500 Mz, DMSO-d6): δ 2.63-2.71 (m, 7H), 3.65 (s, 2H, NCH2), 3.66-3.72 (m, 4H), 6.59-6.62 (m, 1H), 7.33 (s, 1H, thiazole 5-H), 7.81 (d, J=2.0 Hz, 1H), 8.03 (d, J=9.0 Hz, 2H, ArH, C6H4), 8.25 (s, 1H, imidazo[4,5-b]pyridine 5-H), 8.30 (d, J=8.5 Hz, 2H, ArH, C6H4), 8.61 (d, J=2.5 Hz, 1H), 13.54 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z) 3.41 min—535/537 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 535.1028, calculated for C24H24BrN8S (M+H)+: 535.1039.

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