Potassium Carbonate → Methyl 4-{[3-(aminocarbonyl)-6-methoxy-4-(2-toluidino)-7-quinolinyl]oxy}butanoate

HRID 1822832Notes

Reaction equation

HRID 1822832 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C:16]3[C:17]([CH3:22])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:7]([C:12]([NH2:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:23][CH3:24].C([O-])([O-])=O.[K+].[K+].Cl[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36]>CS(C)=O>[NH2:14][C:12]([C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:15][C:16]1[C:17]([CH3:22])=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:4][C:3]([O:23][CH3:24])=[C:2]([O:1][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:11]=2)=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76612Butanoic acid, 4-chloro-, methyl esterHCID 1354329267-Hydroxy-6-methoxy-4-(2-toluidino)-3-quinolinecarboxamide

Product 1

HCID 10224117Methyl 4-{[3-(aminocarbonyl)-6-methoxy-4-(2-toluidino)-7-quinolinyl]oxy}butanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 7-hydroxy-6-methoxy-4-(2-toluidino)-3-quinolinecarboxamide (0.026 g, 0.080 mmol), DMSO (2.5 ml), K2CO3 (0.017 g, 0.12 mmol), and methyl 4-chlorobutanoate (0.011 g, 0.080 mmol) was refluxed for 2 h. The reactionmixture was filtered, evaporated and chromatographed on silica furnishing the title compound.

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationThe reactionmixture was filtered
  3. customevaporated
  4. customchromatographed on silica furnishing the title compound

Sources & evidence

ORD record
ord-8fb98255a31c4e2e8e09edc14a94e809
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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