N,N-Dimethylethylenediamine → 6-(2-Dimethylamino-ethylamino)-3-methoxy-4-methyl-5,10-diaza-benzo[c]fluoren-7-one

HRID 1840407노트

반응식

HRID 1840407 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18]3[C:17]4[CH:16]=[N:15][CH:14]=[CH:13][C:12]=4[C:11](=[O:19])[C:10]=3[C:9](OS(C3C=CC(C)=CC=3)(=O)=O)=[N:8][C:7]=2[C:31]=1[CH3:32].[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][NH2:37]>ClCCl>[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][NH:37][C:9]1[C:10]2[C:11](=[O:19])[C:12]3[CH:13]=[CH:14][N:15]=[CH:16][C:17]=3[C:18]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:31]([CH3:32])[C:7]=2[N:8]=1

참가 물질

4

반응물 2

HCID 66053N,N-DimethylethylenediamineHCID 20829790Toluene-4-sulfonic acid 3-methoxy-4-methyl-7-oxo-7H-5,10-diaza-benzo[c]fluoren-6-yl ester

생성물 1

HCID 234480466-(2-Dimethylamino-ethylamino)-3-methoxy-4-methyl-5,10-diaza-benzo[c]fluoren-7-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

Toluene-4-sulfonic acid 3-methoxy-4-methyl-7-oxo-7H-5,10-diaza-benzo[c]fluoren-6-yl ester (Example 18c-1) (25 mg) was suspended in N,N-dimethylethylenediamine (0.5 ml) and the mixture was stirred at 80° C. for one hour. The mixture was diluted with dichloromethane and washed with saturated ammonium chloride solution and water. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol=50:1 and dichloromethane-methanol=10:1. The desired product was obtained as a reddish powder (21 mg). ESI−MS: m/z 363 (MH+); 1H-NMR (CDCl3): δ2.36 (6H, s), 2.51 (3H, s), 2.66 (2H, t, J=6.5 Hz), 3.82 (2H, quartet like, J=ca 6.5 Hz), 4.02 (3H, s), 7.12 (1H, d, J=9 Hz,), 7.18 (1H, brt, J=ca 5.5 Hz), 7.54 (1H, dd, J=4.5 Hz, 1 Hz), 8.05 (1H, d, J=9 Hz), 8.80 (1H, d, J=4.5 Hz), 9.27 (1H, d, J=1 Hz).

후처리

  1. washwashed with saturated ammonium chloride solution and 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 column chromatography

출처 및 근거

ORD 기록
ord-c1237e161cc442f2874cd9867a7b3e5e
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680326B2

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