Ethyl cyanoacetate → HCID 20083164, compound

HRID 1656755Notes

Reaction equation

HRID 1656755 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].F[C:12]1[C:21]([F:22])=[CH:20][C:19]2[C:23](=[O:31])[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:25][N:17]3[C:18]=2[C:13]=1[CH2:14][CH2:15][N:16]3[CH3:32]>CN(C)C=O>[F:22][C:21]1[C:12]([CH:5]([C:3]#[N:4])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:13]2[C:18]3=[C:19]([C:23](=[O:31])[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:25][N:17]3[N:16]([CH3:32])[CH2:15][CH2:14]2)[CH:20]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 10990475HCID 10990475, compound

Product 1

HCID 20083164HCID 20083164, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

168 mg (4.2 mmol) of 60% sodium hydride was added to 20 ml of N,N-dimethylformamide, and while cooling on ice, 452 mg (4 mmol) of ethyl cyanoacetate was dropped to the solution. The solution was stirred for 1 hour at room temperature. 612 mg (2 mmol) of ethyl 4,5-difluoro-2,3-dihydro-1-methyl-7-oxo-1H,7H-pyrido[3,2,1-ij]cinnoline-8-carboxylate was added to the solution, and the solution was stirred overnight at room temperature. The solution was heated at 70° C. for 2 hours, and the solvent was removed by distillation. 80 ml of chloroform and 20 ml of water were added to the residue, and the solution was acidified with citric acid. The organic layer was separated and after drying over magnesium sulfate, the solvent was removed by distillation. The residue was purified by column chromatography (silica gel 20 g, eluent solvent; ethyl acetate) to obtain 450 mg of the subject compound (161).

Workup

  1. additionwas dropped to the solution
  2. stirringthe solution was stirred overnight at room temperature
  3. temperatureThe solution was heated at 70° C. for 2 hours
  4. customthe solvent was removed by distillation
  5. addition80 ml of chloroform and 20 ml of water were added to the residue
  6. customThe organic layer was separated
  7. dry with materialafter drying over magnesium sulfate
  8. customthe solvent was removed by distillation
  9. customThe residue was purified by column chromatography (silica gel 20 g, eluent solvent; ethyl acetate)

Sources & evidence

ORD record
ord-23b71c5d5d8b498398cd72ec8a7e220a
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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