Reaction Steps
A solution of chloride 95 (367 mg, 1.6 mmol), 3-(4-morpholinyl)propylamine (0.34 mL, 2.3 mmol) and Et3N (0.33 mL, 2.3 mmol) in DME (50 mL) was stirred at reflux temperature for 8 h. The solvent was evaporated and the residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1-oxide 98 (525 mg, 98%) as a yellow solid: mp (MeOH/DCM) 138-140° C.; 1H NMR δ 8.04 (s, 1H, H-9), 7.35 (s, 1H, H-5), 6.10 (br t, J=5.0 Hz, 1H, NH), 3.75 (br t, J=4.7 Hz, 4H, 2×CH2O), 3.56-3.61 (m, 2H, CH2N), 3.08-3.18 (m, 2H, CH2), 2.56-2.65 (m, 3H, CH, CH2), 2.44-2.52 (m, 6H, 3×CH2N), 1.83 (br p, J=6.5 Hz, 2H, CH2), 1.15 (d, J=6.1 Hz, 3H, CH3); 13C NMR δ 158.8, 154.2, 148.9, 142.8, 129.8, 120.7, 114.8, 67.0 (2), 57.3, 53.8 (2), 41.2, 40.8, 40.4, 34.9, 25.3, 20.4. Anal. calcd for C18H25N5O2: C, 63.0; H, 7.3; N, 20.4. Found: C, 63.2; H, 7.2; N, 20.4%.
