Trifluoroacetic acid → N'-methyl-N'-[3-[(5-methylindolo[3,2-b]quinolin-11-yl)amino]propyl]propane-1,3-diamine

Participants

Reaction Steps

To a solution of [3-[methyl-[3-(5-methyl-5H-indolo[3,2-b]quinolin-11-ylamino)-propyl]amino]propyl)-carbamic acid tert-butyl ester (49 mg, 0.1 mmol) in CH2Cl2 (10 ml), was added trifluoroacetic acid (12_l). This mixture was stirred at room temperature for 16 h, at which point the reaction was completed by TLC. All solvents were removed under reduced pressure to give N1-methyl-N1-[3-(5-methyl-5H-indolo[3,2-b]quinolin-11-ylamino)propyl]propane-1,3-diamine (38 mg, 92%) as an oil, which was used directly. 1H-NMR [MeOD,_, ppm]: 8.52 (d, J=8.5 Hz, 1H), 8.35-7.73 (m, 4H), 7.63-7.60 (m, 2H), 7.31 (m, 1H), 4.45 (s, 3H, NCH3), 3.60 (m, 2H, CH2NO), 3.02 (m, 2H, CH2N(CH3)), 2.92 (s, 3H, N(CH3)), 2.36 (m, 4H, 2CH2CN(CH3)), 2.14 (m, 2H, CH2N(CH3)), 1.90 (m, 2H, CH2CN(CH3)).

Provenance & Evidence