Dimethylformamide → HCID 19603281, compound

HRID 1604599Notes

Reaction equation

HRID 1604599 reaction equation
[Cl:1][C:2]1[C:20]([NH:21][C:22](=[O:29])[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=[C:17]([Cl:30])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.IC.[CH3:33]N(C)C=O.[H-].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[C:20]([N:21]([C:22](=[O:29])[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH3:33])=[CH:19][CH:18]=[C:17]([Cl:30])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 196032998-[2,6-Dichloro-3-(3-methoxycarbonylpropionylamino)benzyloxy]-2-methylquinoline

Product 1

HCID 19603281HCID 19603281, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 8-[2,6-dichloro-3-(3-methoxycarbonylpropionylamino)benzyloxy]-2-methylquinoline (447 mg), iodomethane (0.1 ml) and dimethylformamide (5.0 ml) was added sodium hydride (60% in oil, 44 mg) under ice-water cooling. After stirring for 2 hours at the same temperature, the reaction mixture was diluted with ethyl acetate and washed with water twice. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a column chromatography eluted with chloroform to give 8-[2,6-dichloro-3-[N-(3-methyoxycarbonylpropionyl)-N-methylamino]benzyloxy]-2-methylquinoline (310 mg) as a pale yellow oil.

Workup

  1. washwashed with water twice
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by a column chromatography
  5. washeluted with chloroform

Sources & evidence

ORD record
ord-f94b1f8183874f9ea01692849d8eeb55
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

Loading…