Triethylamine → 6-(2-Dimethylamino-ethylsulfanyl)-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one

HRID 1840419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840419
CN(C)CCN[C:6]1[C:18]2[C:17](=[O:19])[C:16]3C=CN=[CH:12][C:11]=3[C:10]=2[C:9]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:8]=2[N:7]=1.Cl.[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][SH:32].[CH2:34]([N:36](CC)[CH2:37]C)C.[H-].[Na+]>CN(C=O)C.ClCCl>[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][S:32][C:6]1[C:18]2[C:17](=[O:19])[C:16]3[CH:37]=[N:36][CH:34]=[CH:12][C:11]=3[C:10]=2[C:9]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:8]=2[N:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 25798Captamine HydrochlorideHCID 99462876-(2-Dimethylamino-ethylamino)-3-methoxy-5,10-diaza-benzo[c]-fluoren-7-one

Produkt 1

HCID 234480346-(2-Dimethylamino-ethylsulfanyl)-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6-chloro-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one (Example 1c-2) (20 mg) was dissolved in DMF (2 ml). To the solution were added 2-dimethylaminoethanethiol hydrochloride (21 mg), triethylamine (0.04 ml) and 60% NaH in paraffin liquid (Kanto Chemical Co. Inc.: 15 mg). The mixture was stirred at room temperature for 5 hours. The reaction mixture was dissolved in dichloromethane and the mixture was washed with water. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel TLC developed by dichloromethane-MeOH-ammonia water (25%)=100:10:1. The desired product (19 mg) was obtained as a yellow solid. ESI−MS: m/z 366 (MH+); 1H-NMR (CDCl3): δ2.41 (6H, s), 2.75 (2H, m), 3.51 (2H, m), 3.99 (3H, s), 7.20 (1H, dd, J=9 Hz, 2.5 Hz), 7.25 (1H, d, J=2.5 Hz), 7.86 (1H, dd, J=5 Hz, 1 Hz), 8.13 (1H, d, J=9 Hz), 8.85 (1H, d, 5 Hz), 8.90 (1H, d, J=1 Hz).

Aufarbeitung

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by silica gel TLC

Quellen und Nachweise

ORD-Eintrag
ord-91cc63eab54e4ed4891fad8809666831
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680326B2

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