1,1'-Carbonyldiimidazole → 1-Cyclohexyl-N-(2-ethoxyethyl)-N-methyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-8-carboxamide

HRID 2068945Notes

Reaction equation

HRID 2068945 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([N:8]([CH2:10][CH2:11][O:12][CH2:13][CH3:14])[CH3:9])=[O:7])=[CH:4][C:3]=1[N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[C:28](N1C=CN=C1)(N1C=CN=C1)=[O:29]>ClC1C=CC=CC=1>[CH:22]1([C:18]2[N:17]3[C:3]4[C:2]([NH:1][C:28](=[O:29])[C:21]3=[CH:20][N:19]=2)=[CH:16][CH:15]=[C:5]([C:6]([N:8]([CH2:10][CH2:11][O:12][CH2:13][CH3:14])[CH3:9])=[O:7])[CH:4]=4)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59198901HCID 59198901, compound

Product 1

HCID 591985551-Cyclohexyl-N-(2-ethoxyethyl)-N-methyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-8-carboxamide

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

4-Amino-3-(2-cyclohexyl-1H-imidazol-1-yl)-N-(2-ethoxyethyl)-N-methylbenzamide as synthesized in Production Example 50, 2.51 g, 1,1′-carbonyldiimidazole 1.32 g and chlorobenzene 32 mL were mixed, and under nitrogen atmosphere, the temperature outside the reactor was heated to 150° C. for 16 hours. Allowing the reaction liquid to cool off, the solvent was distilled off therefrom. To the residue ethyl acetate and brine were added and the organic layer was separated. The organic layer was washed with saturated brine and dried over magnesium sulfate. After distilling the solvent off, the residue was crystallized from t-butyl methyl ether. Further heat-suspending the crystals in ethyl acetate for purification, 993 mg of the title compound was obtained.

Workup

  1. additionwere mixed
  2. customAllowing the reaction liquid
  3. temperatureto cool off
  4. distillationthe solvent was distilled off
  5. additionTo the residue ethyl acetate and brine were added
  6. customthe organic layer was separated
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. distillationAfter distilling the solvent off, the residue
  10. customwas crystallized from t-butyl methyl ether
  11. customfor purification

Sources & evidence

ORD record
ord-4c95e26338454ed49debda48facfeeff
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Reaction notes

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