N,N-Dimethylethylenediamine → 6-(2-Dimethylamino-ethylamino)-3-methoxy-4-methyl-5,10-diaza-benzo[c]fluoren-7-one

HRID 1840407Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18]3[C:17]4[CH:16]=[N:15][CH:14]=[CH:13][C:12]=4[C:11](=[O:19])[C:10]=3[C:9](OS(C3C=CC(C)=CC=3)(=O)=O)=[N:8][C:7]=2[C:31]=1[CH3:32].[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][NH2:37]>ClCCl>[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][NH:37][C:9]1[C:10]2[C:11](=[O:19])[C:12]3[CH:13]=[CH:14][N:15]=[CH:16][C:17]=3[C:18]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:31]([CH3:32])[C:7]=2[N:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Toluene-4-sulfonic acid 3-methoxy-4-methyl-7-oxo-7H-5,10-diaza-benzo[c]fluoren-6-yl ester (Example 18c-1) (25 mg) was suspended in N,N-dimethylethylenediamine (0.5 ml) and the mixture was stirred at 80° C. for one hour. The mixture was diluted with dichloromethane and washed with saturated ammonium chloride solution and water. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol=50:1 and dichloromethane-methanol=10:1. The desired product was obtained as a reddish powder (21 mg). ESI−MS: m/z 363 (MH+); 1H-NMR (CDCl3): δ2.36 (6H, s), 2.51 (3H, s), 2.66 (2H, t, J=6.5 Hz), 3.82 (2H, quartet like, J=ca 6.5 Hz), 4.02 (3H, s), 7.12 (1H, d, J=9 Hz,), 7.18 (1H, brt, J=ca 5.5 Hz), 7.54 (1H, dd, J=4.5 Hz, 1 Hz), 8.05 (1H, d, J=9 Hz), 8.80 (1H, d, J=4.5 Hz), 9.27 (1H, d, J=1 Hz).

Workup

washwashed with saturated ammonium chloride solution and water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated to dryness
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c1237e161cc442f2874cd9867a7b3e5e
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680326B2

Reaction notes

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