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

HRID 1784101

Reaction equation

HRID 1784101 reaction equation
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]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5867271,3-Benzodioxol-4-olHCID 117491774-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline-3-carbonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a5d66199e62444b397bafa9b4178fe74
Source dataset
uspto-grants-2009_03
Patent number
US07501516B2

Linked notes

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