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

HRID 1840416노트

반응식

HRID 1840416 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fe797af18ef3490988c1a09390505726
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680326B2

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