Lithium Hydroxide → HCID 117840608, compound

HRID 714872Notes

Reaction equation

HRID 714872 reaction equation
[C:1]([C@@:3]1([CH2:31][CH3:32])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[C:17]([N:21](S(C)(=O)=O)[S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)[N:9]=2)[C:4]1=[O:30])#[N:2].[OH-].[Li+].[Cl-:35].[NH4+]>O1CCCC1>[ClH:35].[C:1]([C@@:3]1([CH2:31][CH3:32])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[C:17]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)[N:9]=2)[C:4]1=[O:30])#[N:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 117840455HCID 117840455, compound

Product 1

HCID 117840608HCID 117840608, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude N-(3-((4-((3R)-3-cyano-3-ethyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)phenyl)-N-(methylsulfonyl)methanesulfonamide (100 mg) in tetrahydrofuran (3.0 mL) was added 4 M aqueous lithium hydroxide solution (52 μL), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate). To a solution of the residue in ethanol (3.0 mL) was added 1 N hydrochloric acid (72 μL), and the mixture was stirred at room temperature for 5 min. The solvent was evaporated under reduced pressure, and the residue was recrystallized (ethanol/diisopropyl ether) to give the title compound (12 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  6. additionTo a solution of the residue in ethanol (3.0 mL) was added 1 N hydrochloric acid (72 μL)
  7. stirringthe mixture was stirred at room temperature for 5 min
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was recrystallized (ethanol/diisopropyl ether)

Sources & evidence

ORD record
ord-d2c1862df6c048f3aa7f85d0066dfcec
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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