Water → 8-Acetyl-1-cyclohexylimidazo[1,5-a]quinoxalin-4(5H)-one

HRID 72738Notes

Reaction equation

HRID 72738 reaction equation
[CH:1]1([C:7]2[N:11]3[C:12]4[C:17]([NH:18][C:19](=[O:20])[C:10]3=[CH:9][N:8]=2)=[CH:16][CH:15]=[C:14]([C:21](N(C)OC)=[O:22])[CH:13]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][Mg]Br.O1CCCC1.O>O1CCCC1>[C:21]([C:14]1[CH:13]=[C:12]2[C:17]([NH:18][C:19](=[O:20])[C:10]3[N:11]2[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[N:8][CH:9]=3)=[CH:16][CH:15]=1)(=[O:22])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 591987101-Cyclohexyl-N,O-dimethyl-4-oxo-4,5-dihydroimidazo[1,5-a]-quinoxaline-8-hydroxamic acidHCID 178420675HCID 178420675, compound

Product 1

HCID 591988088-Acetyl-1-cyclohexylimidazo[1,5-a]quinoxalin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 354 mg of 1-cyclohexyl-N,O-dimethyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-8-hydroxamic acid as synthesized in above Example 142 in 10 mL of tetrahydrofuran, 1.33 mL of 3M methylmagnesium bromide/tetrahydrofuran solution was added, followed by 3.7 hours' stirring under nitrogen atmosphere and addition of 30 mL of water. The organic layer extracted with ethyl acetate-tetrahydrofuran mixed solvent was washed with water, dried over magnesium sulfate and the solvent therein was distilled off. The crude product was heat-suspended in 10 mL of methanol and purified, to provide 106 mg of the title compound.

Workup

  1. extractionThe organic layer extracted with ethyl acetate-tetrahydrofuran mixed solvent
  2. washwas washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent therein was distilled off
  5. custompurified

Sources & evidence

ORD record
ord-0401822033ca4079a7c084434999e5dc
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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