Water → HCID 53714380, compound

HRID 1604554Notes

Reaction equation

HRID 1604554 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:30]=[CH:29][C:8]([CH:9]=[CH:10][C:11]([NH:13][CH2:14][C:15]([N:17]([C:19]2[C:20]([Cl:28])=[C:21]([C:24]([Cl:27])=[CH:25][CH:26]=2)[CH2:22]Br)[CH3:18])=[O:16])=[O:12])=[CH:7][CH:6]=1)=[O:4].[CH2:31]([O:33][C:34]1[C:43]2[C:38](=[C:39]([OH:44])[CH:40]=[CH:41][CH:42]=2)[N:37]=[C:36]([CH3:45])[CH:35]=1)[CH3:32].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:28][C:20]1[C:19]([N:17]([CH3:18])[C:15](=[O:16])[CH2:14][NH:13][C:11](=[O:12])[CH:10]=[CH:9][C:8]2[CH:29]=[CH:30][C:5]([C:3](=[O:4])[NH:2][CH3:1])=[CH:6][CH:7]=2)=[CH:26][CH:25]=[C:24]([Cl:27])[C:21]=1[CH2:22][O:44][C:39]1[CH:40]=[CH:41][CH:42]=[C:43]2[C:38]=1[N:37]=[C:36]([CH3:45])[CH:35]=[C:34]2[O:33][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221131664-Ethoxy-2-methylquinolin-8-olHCID 538052362,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromide

Product 1

HCID 53714380HCID 53714380, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[N-[4-(methylcarbamoyl)-cinnamoylglycyl]-N-methylamino]-2,6-dichlorobenzyl bromide (60 mg) and 4-ethoxy-8-hydroxy-2-methylquinoline (24.9 mg) in dimethylformamide (0.6 ml) was added potassium carbonate (48.5 mg), and the mixture was stirred for 5 hours at ambient temperature. Water was added thereto, and the mixture was extracted with dichloromethane. The extract was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=15:1, V/V) to give 8-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]-amino]benzyloxy]-4-ethoxy-2-methylquinoline (67 mg) as an amorphous powder.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=15:1, V/V)

Sources & evidence

ORD record
ord-9dda62bb8dc742448909719f820b3116
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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