Diethylenetriamine → HCID 23299879, compound

Participants

Reaction Steps

Reaction of acridine-4-carboxylic acid imidazolide with N,N-bis(2-aminoethyl)amine as above, followed by crystallization of the crude product from MeOH/H2O, gave bis[2-(acridine-4-carboxamido)ethyl]amine (34) (84%). 1H NMR [(CD3)2SO] δ 11.57 (t, J=5.0 Hz, 2 H, 2×CONH), 8.80 (s, 2 H, H-9), 8.46 (d, J=7.1 Hz, 2 H, H-3), 8.08 (d, J=8.4 Hz, 2 H, ArH), 7.92 (d, J=8.7 Hz, 2 H, ArH), 7.79 (d, J=8.1 Hz, 2 H, ArH), 7.55 (t, J=7.7 Hz, 2 H, ArH), 7.41 (t, J=7.6 Hz, 2 H, ArH), 7.27 (t, J=7.4 Hz, 2 H, ArH), 3.73 (q, J=5.5 Hz, 4 H, 2×NHCH2), 3.11 (t, J=5.6 Hz, 4 H, CH2NHCH2). The trihydrochloride salt crystallized from MeOH/EtOAc/HCl, mp 182-184° C. Anal. (C32H27N5O2.3HCl) C, H, N, Cl.

Provenance & Evidence