Hydrochloric Acid → HCID 58574952, compound

HRID 1189492Notes

Reaction equation

HRID 1189492 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[N:18]2[C:19]3[C:24]([NH:25][C:26](=[O:27])[C:17]2=[CH:16][N:15]=1)=[CH:23][C:22]([C:28]([N:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31]1)=[O:29])=[C:21]([CH3:39])[CH:20]=3)(C(C)(C)C)(C)C.Cl>CO>[CH2:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:38][N:30]1[C:28]([C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[CH3:39])[N:18]1[C:14]([C@@H:10]3[CH2:11][CH2:12][CH2:13][C@@H:9]3[OH:8])=[N:15][CH:16]=[C:17]1[C:26](=[O:27])[NH:25]2)=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58575551HCID 58575551, compound

Product 1

HCID 58574952HCID 58574952, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 560 mg of 1-[cis-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl]-7-(1,3-dihydro-2H-isoindol-2-ylcarbonyl)-8-methylimidazo[1,5-a]quinoxalin-4(5H)-one and 20.0 mL of methanol was added 0.2 mL of concentrated hydrochloric acid, followed by stirring at room temperature overnight. The reaction liquid was concentrated under reduced pressure, and then, the residue was dissolved in water. A saturated aqueous sodium hydrogen carbonate solution was added thereto to adjust the pH to about 5, followed by extraction with a mixed solvent of chloroform/methanol=4/1, the organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=97/3-90/10) to give a powder from 2-propanol, thereby obtaining 333 mg of 7-(1,3-dihydro-2H-isoindol-2-ylcarbonyl)-1-[cis-2-hydroxycyclopentyl]-8-methylimidazo[1,5-a]quinoxalin-4(5H)-one as a colorless solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. additionA saturated aqueous sodium hydrogen carbonate solution was added
  5. extractionfollowed by extraction with a mixed solvent of chloroform/methanol=4/1
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=97/3-90/10)
  9. customto give a powder from 2-propanol

Sources & evidence

ORD record
ord-88edf33c20ac4b5c9dbc9b405b08ba62
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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