Reaction Steps
A suspension of the compound 111 (306 mg, 0.7 mmol), morpholine (61.0 mg, 0.7 mmol) and paraformaldehyde (22.0 mg, 0.733 mmol) in ethyl acetate (4 mL) was heated under reflux in an atmosphere of nitrogen for 3 days. After cooling down at room temperature, the residue was purified by chromatography on a silica gel column (eluate: ethyl acetate - methanol (5:1)) to give the compound 113 (265 mg, 69%). Rf 0.63 (5:1 EtOAc-CH3OH). 1H-NMR (CDCl3): δH1.30 (6 H, d, J 6.9 Hz, (CH3)2CH), 2.44 (4H, m, N(CH2CH2)2O), 3.18 (1 H, sep, J 6.9 Hz, (CH3)2CH), 3.65 (4 H, m, N(CH2CH2)2O), 3.91 (2 H, d, J 6.6 Hz, NCH2NH), 4.98 (1 H, t, J 6.6 Hz, NCH2NH ), 5.19 (2 H, s, CH2O), 5.25 (2 H, s, NCH2 ), 6.69 (2 H, d, J 1.8 Hz, arom 2- and 6-H), 6.71 (2 H, d-like, 4-pyridyl 2- and 6-H), 7.05 (1 H, t, J 1.8 Hz, arom 4-H), 8.45 (2 H, d-like, 4-pyridyl 3- and 5-H). Elementary analysis (for C25H29N5O2SCl2) Calcd. : C, 54.55% H, 5.31% N, 12.72% S, 5.82% Cl, 12.88% Found: C, 54.37% H, 5.36% N, 12.80% S, 5.92% Cl, 12.64% hydrochloride of 113 Elementary analysis (for C25H32N5O3SCl5 3HCl 3H2O) Calcd. : C, 42.06% H, 5.36% N, 9.81% S, 4.40% Cl, 24.83% Found: C, 42.01% H, 5.34% N, 10.01% S, 4.73% Cl, 24.92%.
