Dimethylformamide → 1-(1-Ethylpropyl)-8-methoxy-N,N-dimethyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxamide

HRID 2068941Notes

Reaction equation

HRID 2068941 reaction equation
[CH2:1]([CH:3]([C:6]1[N:10]2[C:11]3[C:16]([NH:17][C:18](=[O:19])[C:9]2=[CH:8][N:7]=1)=[CH:15][C:14]([C:20](O)=[O:21])=[C:13]([O:23][CH3:24])[CH:12]=3)[CH2:4][CH3:5])[CH3:2].[CH3:25][N:26](C)[CH:27]=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.CNC>O>[CH2:4]([CH:3]([C:6]1[N:10]2[C:11]3[C:16]([NH:17][C:18](=[O:19])[C:9]2=[CH:8][N:7]=1)=[CH:15][C:14]([C:20]([N:26]([CH3:27])[CH3:25])=[O:21])=[C:13]([O:23][CH3:24])[CH:12]=3)[CH2:1][CH3:2])[CH3:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 591987141-(1-Ethylpropyl)-8-methoxy-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxaline-7-carboxyic acid

Product 1

HCID 591986961-(1-Ethylpropyl)-8-methoxy-N,N-dimethyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(1-Ethylpropyl)-8-methoxy-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxaline-7-carboxylic acid as synthesized in above Example 32, 329 mg, N,N-dimethylformamide 5 mL and 1,1′-carbonyldiimidazole 275 mg were mixed and stirred for an hour at room temperature in nitrogen atmosphere. Dimethylamine hydrochloride 816 mg was added, followed by 5.5 hours' stirring. The reaction mixture was diluted with water, extracted with ethyl acetate and washed with saturated saline. The extract was dried over anhydrous sodium sulfate, and from which the solvent was distilled off. To the residue tert-butyl methyl ether was added, heated under stirring, and the precipitate was recovered by filtration, followed by washing with tert-butyl methyl ether. The product was dried in flowing air (40° C.) to provide 223 mg of the title compound.

Workup

  1. additionwere mixed
  2. stirring' stirring
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated saline
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. distillationfrom which the solvent was distilled off
  7. additionTo the residue tert-butyl methyl ether was added
  8. temperatureheated
  9. stirringunder stirring
  10. filtrationthe precipitate was recovered by filtration
  11. washby washing with tert-butyl methyl ether
  12. customThe product was dried
  13. customair (40° C.)

Sources & evidence

ORD record
ord-814a9d78dae7464598f9d06a57641283
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Reaction notes

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