Sulfuric Acid → HCID 118079709, compound

HRID 1485736Notes

Reaction equation

HRID 1485736 reaction equation
S(=O)(=O)(O)O.[CH3:6][C@H:7]1[CH2:12][N:11](S(C2C=CC(C)=CC=2)(=O)=O)[C:10]2[CH:23]=[C:24]([C:27]3[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=3)[N:25]=[CH:26][C:9]=2[N:8]1[C:37](=[O:39])[CH3:38].[OH-].[Na+]>ClCCl>[CH3:6][C@H:7]1[CH2:12][NH:11][C:10]2[CH:23]=[C:24]([C:27]3[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:31][CH:32]=3)[N:25]=[CH:26][C:9]=2[N:8]1[C:37](=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 118079848HCID 118079848, compound

Product 1

HCID 118079709HCID 118079709, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfuric acid (0.5 mL, 9.4 mmol) was added to (S)-1-(3-methyl-7-(4-(methylsulfonyl)phenyl)-1-tosyl-2,3-dihydropyrido[4,3-b]pyrazin-4(1H)-yl)ethanone (0.006 g, 0.012 mmol) and the mixture was stirred until all the solid had dissolved (10 min). After 10 min, ice was added, and the solution was basified by the slow addition of 6 M aqueous sodium hydroxide solution. Dichloromethane was added and the layers were separated. The aqueous phase was extracted with dichloromethane and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford (S)-1-(3-methyl-7-(4-(methylsulfonyl)phenyl)-2,3-dihydropyrido[4,3-b]pyrazin-4(1H)-yl)ethanone (0.004 g, 96%) as an off-white solid. MS (ESI, pos. ion) m/z 346.

Workup

  1. dissolutionhad dissolved (10 min)
  2. additionice was added
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ca8c91dc8f19461fbf17d32d28572b88
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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