Water → HCID 68981429, compound

HRID 1783728Notes

Reaction equation

HRID 1783728 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH3:13])=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1.[H-].[Na+].[CH3:20][O:21][CH2:22][C:23](Cl)=[O:24].O>CN(C=O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]([CH3:13])[C:23](=[O:24])[CH2:22][O:21][CH3:20])=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 96623Methoxyacetyl chlorideHCID 21106565HCID 21106565, compound

Product 1

HCID 68981429HCID 68981429, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Bromo-2-isopropyl-7-methylamino-2H-phthalazin-1-one (0.5 g, 1.69 mmol) was dissolved in DMF (5 ml). To this was added NaH (60%, 0.19 g, 5.1 mmol) as a suspension in DMF (2 ml). The mixture was stirred at RT for 30 min then methoxyacetyl chloride (0.27 g, 2.5 mmol) was added dropwise and the reaction mixture was stirred at RT for 24 hours. After this time, water (10 ml) was added cautiously, the mixture was extracted with EtOAc (3×10 ml), the organic layers were combined, dried (MgSO4), filtered and concentrated under vacuum. Flash column chromatography (elution: 50% hexane, 50% EtOAc) gave the title compound (0.47 g, 76% yield) as a white solid.

Workup

  1. stirringthe reaction mixture was stirred at RT for 24 hours
  2. extractionthe mixture was extracted with EtOAc (3×10 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. washFlash column chromatography (elution: 50% hexane, 50% EtOAc)

Sources & evidence

ORD record
ord-49332a5f9c03447d85bbd807a0c7d77e
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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