N,N-Dimethylethylenediamine → 6-(2-Dimethylamino-ethylamino)-3-ethoxy-5,9-diaza-benzo[c]fluoren-7-one

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Reaktionsgleichung

Cl[C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[CH:19][C:4]=2[N:3]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH2:27]>ClCCl>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH:27][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[CH:19][C:4]=2[N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

6-Chloro-3-ethoxy-5,9-diaza-benzo[c]fluoren-7-one (Example 34b) (14 mg) was suspended in N,N-dimethylethylenediamine (0.3 ml) and the mixture was stirred at 70° C. for 30 min. The reaction mixture was diluted with dichloromethane and washed with saturated ammonium chloride solution and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography developed by dichloromethane-methanol-ammonia water (28%)=15:1:0.1. The desired product was obtained as a reddish powder (16 mg). ESI−MS: m/z 363 (MH+); 1H-NMR (CDCl3): δ1.50 (3H, t, J=7 Hz), 2.36 (6H, s), 2.65 (2H, t, J=6.5 Hz), 3.78 (2H, quartet like, J=ca 6 Hz), 4.20 (2H, q, J=7 Hz), 6.97 (1H, dd, J=9 Hz, 2.5 Hz), 7.06 (1H, d, J=2.5 Hz), 7.34 (1H, brt, J=ca 5 Hz), 7.87 (1H, dd, J=5 Hz, 1 Hz), 8.04 (1H, d, J=9 Hz), 8.83 (1H, d, J=5 Hz), 8.86 (1H, d, J=1 Hz).

Aufarbeitung

washwashed with saturated ammonium chloride solution and brine
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated to dryness
customThe residue was purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag: ord-fe797af18ef3490988c1a09390505726
Quelldatensatz: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06680326B2

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