N,N-二甲基乙二胺 → 6-(2-Dimethylamino-ethylamino)-3-methoxy-4-methyl-5,10-diaza-benzo[c]fluoren-7-one

HRID 1840407笔记

反应方程式

HRID 1840407 反应方程式
[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

参与物

4

反应物 2

HCID 66053N,N-二甲基乙二胺HCID 20829790Toluene-4-sulfonic acid 3-methoxy-4-methyl-7-oxo-7H-5,10-diaza-benzo[c]fluoren-6-yl ester

产物 1

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

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

反应条件

温度
80 °C

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-c1237e161cc442f2874cd9867a7b3e5e
来源数据集
uspto-grants-2004_01
专利号
US06680326B2

反应笔记

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