N,N-Dimethylethylenediamine → 6-(2-Dimethylamino-ethylamino)-3-methoxy-5,10-diaza-benzo[c]-fluoren-7-one

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Reaction Conditions

Reaction Steps

6-Chloro-3-methoxy-5,10-diaza-benzo[c]fluoren-7-one (Example 1c-1) (120 mg) was suspended in N,N-dimethylethylenediamine (50 ml) and the mixture was stirred at 55° C. for four hours under Ar. N,N-dimethylethylenediamine was evaporated and the residue was dissolved in dichloromethane. The solution was washed with water and dried over anhydrous sodium sulfate. Dichloromethane was evaporated to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol-ammonia water (28%)=400:20:1 and dichloromethane-methanol-ammonia water (25%)=300:20:1. The desired product was obtained as a reddish powder. ESI−MS: m/z 349 (MH+); 1H-NMR (CDCl3): δ2.41 (6H, s), 2.72 (2H, t, J=6 Hz), 3.82 (2H, q-like, J=ca 6 Hz), 3.97 (3H, s), 7.00 (1H, dd, J=9 Hz, 2.5 Hz), 7.07 (1H, d, J=2.5 Hz), 7.34 (1H, brt, J=ca 5 Hz), 7.55 (1H, dd, J=4.5 Hz, 1 Hz), 8.05 (1H, d, J=9 Hz), 8.81 (1H, d, 4.5 Hz), 9.27 (1H, d, J=1 Hz).

Provenance & Evidence