碳酸钾 → 3-Cyano-6-methoxy-4-(2,3-methylenedioxyphenoxy)-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline

HRID 1784101

反应方程式

HRID 1784101 反应方程式
C(=O)([O-])[O-].[K+].[K+].[CH2:7]1[O:15][C:14]2[C:9](=[C:10]([OH:16])[CH:11]=[CH:12][CH:13]=2)[O:8]1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH2:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][C:19]=1[C:41]#[N:42]>CN(C=O)C>[C:41]([C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:18]=1[O:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]3[O:15][CH2:7][O:8][C:9]=13)=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH2:31][CH2:32][CH2:33][N:34]1[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]1)[CH:23]=2)#[N:42]

参与物

5

反应物 3

HCID 11430碳酸钾HCID 5867271,3-亚甲二氧基-4-苯酚HCID 117491774-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline-3-carbonitrile

产物 1

HCID 179805913-Cyano-6-methoxy-4-(2,3-methylenedioxyphenoxy)-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline收率 54.3%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

Potassium carbonate-(0.055 g) was added to a solution of 2,3-methylenedioxyphenol (0.041 g) in DMF (3 ml) and the mixture was stirred at ambient temperature for 10 minutes. 4-Chloro-3-cyano-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline (0.1 g) was added and the mixture was stirred and heated to 95° C. for 2 hours. The resultant mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was purified by colum chromatography on silica using initially increasingly polar mixtures of methylene chloride and methanol followed by increasingly polar mixtures of methylene chloride and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.069 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 2.3-2.4 (m, 2H), 3.0 (s, 3H), 3.2-4.0 (m, 8H), 3.5 (m, 2H), 3.95 (s, 3H), 4.4 (m, 2H), 6.05 (s, 2H), 6.8 (m, 1H), 6.9 (m, 2H), 7.6 (s, 1H), 7.62 (s, 1H), 9.1 (s, 1H); Mass Spectrum: M+H+ 477.

后处理

  1. stirringthe mixture was stirred
  2. temperatureheated to 95° C. for 2 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue was purified by colum chromatography on silica using initially increasingly polar mixtures of methylene chloride and methanol
  6. temperatureby increasingly polar mixtures of methylene chloride

来源与证据

ORD记录
ord-a5d66199e62444b397bafa9b4178fe74
来源数据集
uspto-grants-2009_03
专利号
US07501516B2

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