Sodium hydride → HCID 66826506, compound

HRID 1912456Notes

Reaction equation

HRID 1912456 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:15][C:16](=[O:19])[CH2:17]Cl)([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:9])[NH:15][C:16](=[O:19])[CH2:17][N:11]3[N:12]=[CH:13][CH:14]=[C:10]23)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 178465117HCID 178465117, compound

Product 1

HCID 66826506HCID 66826506, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of rac-N-[1-(3-bromo-phenyl)-1-(1H-pyrazol-3-yl)-ethyl]-2-chloro-acetamide (1.22 g, 3.56 mmol) in THF (40 mL) was added dropwise to a suspension of sodium hydride (0.28 g, 7.12 mmol) in THF (40 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 1 hour. The mixture was diluted with water and the product extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 50/50 to 100/0). The desired fractions were collected and concentrated in vacuo to yield rac-4-(3-bromo-phenyl)-4-methyl-4,5-dihydro-pyrazolo[1,5-a]pyrazin-6-one (0.7 g, 64% yield) as a white solid.

Workup

  1. extractionthe product extracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 50/50 to 100/0)
  7. customThe desired fractions were collected
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06db5173ae064d158d34b922ebf30e68
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

Loading…