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

HRID 72735Notes

Reaction equation

HRID 72735 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-f07d2307d8b946209f913d545d284325
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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