Reaction Steps
A mixture of N4-(4-Aminophenyl)-N6,N6-dimethyl-4,6-quinolinediamine (181 mg, 0.58 mmol), 3-acetylbenzoic acid (M1) (97 mg, 0.58 mmol) and EDCI (220 mg, 0.1.16 mmol) in DMF (5 mL) was stirred at 20° C. for 5 min. Then DMAP (140 mg, 1.16 mmol) was added and the reaction mixture was stirred at 20° C. for 24 h. The solvent was removed under reduced pressure and residue was stirred in aqueous NaHCO3 for 1 h. The resulting precipitate was filtered and purified by chromatography in SiO2 eluting with a gradient (0-7.5%) of MeOH/DCM to give M2 (113 mg, 42%); mp (DCM/MeOH)>280° C.; 1HNMR [(CD3)2SO] δ14.02 (br, 1 H, N+H), 10.66 (s, 1 H, NH), 10.31 (s, 1 H, NH), 8.53 (t, J=1.6 Hz, 1 H, ArH), 8.28 (d, J=6.7 Hz, 1 H, ArH), 8.24 (td, J=8.1, 1.5 Hz, 1 H, ArH), 8.19 (td, J=7.8, 2.8 Hz, 1 H, ArH), 8.00 (d, J=6.8 Hz, 2 H, ArH), 7.87 (d, J=9.4 Hz, 1 H, ArH), 7.78 (t, J=7.8 Hz, 1 H, ArH), 7.64 (dd, J=9.4, 2.6 Hz, 1 H, ArH), 7.51 (d, J=2.5 Hz, 1 H, ArH), 7.47 (d, J=8.8 Hz, 2 H, ArH), 6.69 (d, J=6.7 Hz, 1 H, ArH), 3.09 [s, 6 H, (NCH3)2], 2.68 (s, 3 H, COCH3); APCI+ve 425.
