Sodium hydride → HCID 118023214, compound

HRID 929308Notes

Reaction equation

HRID 929308 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[H-].[Na+].Cl[CH2:10][CH2:11][C:12]([N:14]([C:16]1[C:17]([Cl:27])=[N:18][N:19]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:20]=1)[CH3:15])=[O:13]>CN(C=O)C.[NH4+].[Cl-].CCOC(C)=O.[Na+].[Cl-]>[Cl:27][C:17]1[C:16]([N:14]([CH3:15])[C:12](=[O:13])[CH2:11][CH2:10][N:3]2[CH2:4][CH2:5][O:1][C:2]2=[O:6])=[CH:20][N:19]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[N:18]=1

Participants

8

Reactant 3

HCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 89871667HCID 89871667, compound

Product 1

HCID 118023214HCID 118023214, compound

Reagents, catalysts & solvents 4

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of oxazolidin-2-one (0.038 g, 0.44 mmol) in DMF (3 mL) was added NaH (60% dispersion in oil, 0.011 g, 0.44 mmol). The mixture was stirred at a temperature of about 0° C. for 10 minutes, and 3-chloro-N-(3-chloro-1-(pyridin-3-yl)-1H- pyrazol-4-yl)-N-methyl propanamide (0.12 g, 0.40 mmol) was added. The resulting brown-yellow mixture was stirred at room temperature for two hours and diluted with saturated aqueous NH4Cl. The mixture was diluted with EtOAc and saturated aqueous NaCl solution. The organic phase was separated, and the aqueous phase extracted with EtOAc (2×50 mL). The combined EtOAc extracts was dried over MgSO4, filtered, and concentrated under reduced pressure to give light brown gum. The gum was purified on silica gel eluting with MeOH/CH2Cl2 to give the title compound F31 as a colorless oil (0.13 g, 94%).

Workup

  1. stirringThe resulting brown-yellow mixture was stirred at room temperature for two hours
  2. customThe organic phase was separated
  3. extractionthe aqueous phase extracted with EtOAc (2×50 mL)
  4. dry with materialThe combined EtOAc extracts was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give light brown gum
  8. customThe gum was purified on silica gel eluting with MeOH/CH2Cl2

Sources & evidence

ORD record
ord-5d7e538cb3a24f2da012ef446e874299
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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