Hydrochloric Acid → HCID 58575179, compound

HRID 1189465Notes

Reaction equation

HRID 1189465 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[N:15]4[C:16]5[C:21]([NH:22][C:23](=[O:24])[C:14]4=[CH:13][N:12]=3)=[CH:20][C:19]([C:25]([O:27][CH3:28])=[O:26])=[C:18]([CH3:29])[CH:17]=5)[CH2:7][CH2:6]2)[O:4]CC1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:29][C:18]1[CH:17]=[C:16]2[C:21]([NH:22][C:23](=[O:24])[C:14]3[N:15]2[C:11]([CH:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)=[N:12][CH:13]=3)=[CH:20][C:19]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58575323HCID 58575323, compound

Product 1

HCID 58575179HCID 58575179, compoundYield 125.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

270 mg of methyl 1-(1,4-dioxaspiro[4.5]decan-8-yl)-8-methyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylate was added to 10 mL of tetrahydrofuran, and 2 mL of 1 M hydrochloric acid was added thereto under ice-cooling, followed by stirring at room temperature for 3 days. To the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution to adjust the pH to about 7, followed by extraction with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 301 mg of methyl 8-methyl-4-oxo-1-(4-oxocyclohexyl)-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylate as a yellow solid.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-70fa67b92ac64e30b5176c6a8f79b42b
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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