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

HRID 1840401ノート

反応式

HRID 1840401 の反応式
Cl[C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[CH:10][N:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:4]=2[N:3]=1.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH:26][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[CH:10][N:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:4]=2[N:3]=1

参加物

3

反応物 2

HCID 66053N,N-DimethylethylenediamineHCID 113923176-Chloro-3-methoxy-5,10-diaza-benzo[c]fluoren-7-one

生成物 1

HCID 99462876-(2-Dimethylamino-ethylamino)-3-methoxy-5,10-diaza-benzo[c]-fluoren-7-one

反応条件

温度
55 °C

実験手順

6-Chloro-3-methoxy-5,10-diaza-benzo[c]fluoren-7-one (Example 1c-1) (120 mg) was suspended in N,N-dimethylethylenediamine (50 ml) and the mixture was stirred at 55° C. for four hours under Ar. N,N-dimethylethylenediamine was evaporated and the residue was dissolved in dichloromethane. The solution was washed with water and dried over anhydrous sodium sulfate. Dichloromethane was evaporated to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol-ammonia water (28%)=400:20:1 and dichloromethane-methanol-ammonia water (25%)=300:20:1. The desired product was obtained as a reddish powder. ESI−MS: m/z 349 (MH+); 1H-NMR (CDCl3): δ2.41 (6H, s), 2.72 (2H, t, J=6 Hz), 3.82 (2H, q-like, J=ca 6 Hz), 3.97 (3H, s), 7.00 (1H, dd, J=9 Hz, 2.5 Hz), 7.07 (1H, d, J=2.5 Hz), 7.34 (1H, brt, J=ca 5 Hz), 7.55 (1H, dd, J=4.5 Hz, 1 Hz), 8.05 (1H, d, J=9 Hz), 8.81 (1H, d, 4.5 Hz), 9.27 (1H, d, J=1 Hz).

後処理

  1. customN,N-dimethylethylenediamine was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customDichloromethane was evaporated to dryness
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fd52883d99e4463a826ae0d780ec5f07
出典データセット
uspto-grants-2004_01
特許番号
US06680326B2

反応ノート

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