N,N-Dimethylethylenediamine → 6-(2-Dimethylamino-ethylamino)-3-ethoxy-5,9-diaza-benzo[c]fluoren-7-one

HRID 1840416ノート

反応式

HRID 1840416 の反応式
Cl[C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[CH:19][C:4]=2[N:3]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH2:27]>ClCCl>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH:27][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[CH:19][C:4]=2[N:3]=1

参加物

4

反応物 2

HCID 66053N,N-DimethylethylenediamineHCID 234480226-Chloro-3-ethoxy-5,9-diaza-benzo[c]fluoren-7-one

生成物 1

HCID 101332606-(2-Dimethylamino-ethylamino)-3-ethoxy-5,9-diaza-benzo[c]fluoren-7-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

6-Chloro-3-ethoxy-5,9-diaza-benzo[c]fluoren-7-one (Example 34b) (14 mg) was suspended in N,N-dimethylethylenediamine (0.3 ml) and the mixture was stirred at 70° C. for 30 min. The reaction mixture was diluted with dichloromethane and washed with saturated ammonium chloride solution and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography developed by dichloromethane-methanol-ammonia water (28%)=15:1:0.1. The desired product was obtained as a reddish powder (16 mg). ESI−MS: m/z 363 (MH+); 1H-NMR (CDCl3): δ1.50 (3H, t, J=7 Hz), 2.36 (6H, s), 2.65 (2H, t, J=6.5 Hz), 3.78 (2H, quartet like, J=ca 6 Hz), 4.20 (2H, q, J=7 Hz), 6.97 (1H, dd, J=9 Hz, 2.5 Hz), 7.06 (1H, d, J=2.5 Hz), 7.34 (1H, brt, J=ca 5 Hz), 7.87 (1H, dd, J=5 Hz, 1 Hz), 8.04 (1H, d, J=9 Hz), 8.83 (1H, d, J=5 Hz), 8.86 (1H, d, J=1 Hz).

後処理

  1. washwashed with saturated ammonium chloride solution and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-fe797af18ef3490988c1a09390505726
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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