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

HRID 1840416Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-fe797af18ef3490988c1a09390505726
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680326B2

Reaction notes

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