Hydrochloric Acid → HCID 68018985, compound

HRID 1396680Notes

Reaction equation

HRID 1396680 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][C:22]=3[CH3:23])[N:19]3[C:24]([C@@H:27]5[CH2:31][CH2:30][CH2:29][C@@H:28]5[O:32][Si](C(C)(C)C)(C)C)=[N:25][CH:26]=[C:18]3[C:17](=[O:40])[NH:16]4)=[O:12])[C:5]2=[N:6][CH:7]=1.Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][C:22]=3[CH3:23])[N:19]3[C:24]([C@@H:27]5[CH2:31][CH2:30][CH2:29][C@@H:28]5[OH:32])=[N:25][CH:26]=[C:18]3[C:17](=[O:40])[NH:16]4)=[O:12])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86701164HCID 86701164, compound

Product 1

HCID 68018985HCID 68018985, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 369 mg of 7-[(5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)carbonyl]-1-(cis-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)-8-methylimidazo[1,5-a]quinoxalin-4(5H)-one and 3.70 mL of methanol was added 0.15 mL of concentrated hydrochloric acid, followed by stirring at room temperature for 3 days. The solvent was evaporated under reduced pressure, then the residue was dissolved in water, and a saturated aqueous sodium hydrogen carbonate solution was added thereto to adjust the pH to about 8. The mixture was extracted with chloroform, the organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0-95/5) and triturated with methanol to obtain 221 mg of 7-[(5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)carbonyl]-1-(cis-2-hydroxycyclopentyl)-8-methylimidazo[1,5-a]quinoxalin-4(5H)-one as a colorless solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. additiona saturated aqueous sodium hydrogen carbonate solution was added
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0-95/5)
  8. customtriturated with methanol

Sources & evidence

ORD record
ord-8fba594b4edd45509ebc973856991918
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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