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

HRID 1840419Notes

Reaction equation

HRID 1840419 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-91cc63eab54e4ed4891fad8809666831
Source dataset
uspto-grants-2004_01
Patent number
US06680326B2

Reaction notes

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