反应详情

温度

85 °C

To a mixture of 5-bromo-4-(4-((2-isopropyloxazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (0.070 g, 0.16 mmol), EtOH (3 mL), and p-anisaldehyde (0.025 g, 0.18 mmol) in EtOH (1 mL) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.49 mL, 0.49 mmol). The reaction mixture was heated at 85° C. for 5 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on preparative silica TLC plates, which were eluted with dichloromethane/ethyl acetate (v/v; 1:1). The title compound was isolated as a pale yellow solid (0.019 g, 23%) after trituration with diethyl ether; 1H-NMR (500 Mz, DMSO-d6): δ 1.27 (d, J=7 Hz, 6H, iPr—CH3), 2.65 (m, 4H, piperazine N(CH2)2), 3.05 (m, 1H, iPr—CH), 3.44 (s, 2H, NCH2), 3.65 (m, 4H, piperazine N(CH2)2), 3.84 (s, 3H, OMe), 7.10 (d, J=7.5 Hz, 2H, ArH), 7.86 (s, 1H, oxazole 5-H), 8.13 (d, J=9.0 Hz, 2H, ArH), 8.20 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.30 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z) 3.45 min—511/514 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 511.1457, calculated for C24H28BrN6O2 (M+H)+: 511.1457.

1. additionwas added
2. temperatureto cool to room temperature
3. customthe solvents were removed in vacuo
4. customThe residue was absorbed on preparative silica TLC plates, which
5. washwere eluted with dichloromethane/ethyl acetate (v/v; 1:1)