Dimethylformamide → HCID 12991196, compound

HRID 1582988Notes

Reaction equation

HRID 1582988 reaction equation
CN([CH:4]=[O:5])C.[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[C:22]3[C:17](=[N:18][C:19]([CH3:23])=[CH:20][CH:21]=3)[N:16]([CH2:24][CH3:25])[C:15](=[O:26])[C:14]=2[CH2:27][CH2:28][CH2:29][OH:30])[CH:10]=[CH:11][CH:12]=1.[C:31](=O)([O-])[O-:32].[K+].[K+].CI>O>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[C:22]3[C:17](=[N:18][C:19]([CH3:23])=[CH:20][CH:21]=3)[N:16]([CH2:24][CH3:25])[C:15](=[O:26])[C:14]=2[CH2:27][CH2:28][CH2:29][O:30][C:31]([O:5][CH3:4])=[O:32])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 12991190HCID 12991190, compound

Product 1

HCID 12991196HCID 12991196, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a 10 ml DMF solution containing 500 mg of 4-(3-chlorophenyl)-1-ethyl-3-(3-hydroxypropyl)-7-methyl-1,8-naphthyridin-2(1H)-one were added 500 mg of potassium carbonate and 0.5 ml of methyl iodide, followed by stirring under heating at an oil bath temperature of 80° C. for 2 hours. Thereafter, 1.0 g of potassium carbonate and 1.0 ml of methyl iodide were further added thereto, followed by stirring under heating at an oil bath temperature of 80° C. for a whole day and night. After the reaction mixture was cooled to room temperature, water was added thereto, and the whole was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by a silica gel column chromatography (hexane-ethyl acetate) and then recrystallized from hexane-diisopropyl ether to obtain 160 mg of 4-(3-chlorophenyl)-1-ethyl-3-[3-(methoxycarbonyloxy)propyl]-7-methyl-1,8-naphthyridin-2(1H)-one as colorless crystals.

Workup

  1. stirringby stirring
  2. temperatureunder heating at an oil bath temperature of 80° C. for a whole day
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. extractionthe whole was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
  9. customrecrystallized from hexane-diisopropyl ether

Sources & evidence

ORD record
ord-1efdfd60d28a474a893455ca29231c95
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

Loading…