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

HRID 1840419ノート

反応式

HRID 1840419 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-91cc63eab54e4ed4891fad8809666831
出典データセット
uspto-grants-2004_01
特許番号
US06680326B2

反応ノート

読み込み中…