N,N-Dimethylethylenediamine → Pyrido[4,3-a]phenazine-11-carboxamide, N-[2-(dimethylamino)ethyl]-

Participants

Reaction Conditions

Reaction Steps

A mixture of pyrido[4,3-α]phenazine-11-carboxylic acid (II.3) (0.11 g, 0.38 mmol) and CDI (0.12 g, 0.76 mmol) in DMF (5 mL) was heated and stirred at 50-60° C. for 2 h. N,N-Dimethylethylenediamine (0.5 mL, excess) was then added, and the mixture was stirred at room temperature for 2 h. The DMF was removed under reduced pressure, and the residue was diluted with water. The resulting precipitate was collected and crystallized from CH2Cl2/hexane to give pyrido[4,3-α]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (0.11 g, 84%): mp 213-215° C.; 1H NMR [CDCl3] δ 2.48 [s, 6 H, N(CH3)2], 2.75 [t, J=5.7 Hz, 2 H, CH2N(CH3)2], 3.89 (q, J=5.5 Hz, 2 H, CH2NH), 8.03-8.14 (m, 3 H, 3xArH), 8.42 (dd, J=8.4, 1.5 Hz, 1 H, ArH), 9.00 (d, J=5.5 Hz, 1 H, H-1 or H-2), 9.07 (dd, J=7.2, 1.5 Hz, 1 H, H-10), 9.34 (s, 1 H, H-4), 9.36 (d, J=5.5 Hz, 1 H, H-1 or H-2), 10.66 (br, 1 H, CONH).

Provenance & Evidence