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

HRID 72731Notes

Reaction equation

HRID 72731 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].[C:25](N1C=CN=C1)([N:27]1C=CN=[CH:28]1)=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:27]([CH3:28])[CH3:25])=[O:21])=[C:13]([O:23][CH3:24])[CH:12]=3)[CH2:1][CH3:2])[CH3:5]

Participants

5

Reactant 3

HCID 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-carboxyic acid as synthesized in above Example 32, 329 mg, N,N-diimethylformamide 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-9475eb8727d442dcb4e244d6a6ce9b34
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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