Water → HCID 21106564, compound

HRID 1765350Notes

Reaction equation

HRID 1765350 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+].Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.O>CN(C)C=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]([CH3:13])[CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[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 767274-(2-Chloroethyl)morpholineHCID 21106565HCID 21106565, compound

Product 1

HCID 21106564HCID 21106564, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

4-Bromo-2-isopropyl-7-methylamino-2H-phthalazin-1-one (0.13 g, 0.44 mmol) was dissolved in dimethylformamide (DMF) (5 ml). To this was added NaH (60%, 0.053 g, 1.3 mmol) as a suspension in DMF (2 ml). The mixture was stirred at room temperature for 30 minutes then 4-(2-Chloro-ethyl)-morpholine (0.12 g, 0.66 mmol) was added in one portion as a solution in DMF (1 ml) and the reaction mixture was heated to 70° C. for 24 hours. After this time, the reaction mixture was cooled to room temperature and water (10 ml) was added cautiously, the mixture was extracted with ethyl acetate (3×10 ml), the organic layers were combined, dried (MgSO4), filtered and concentrated under vacuum. Flash column chromatography (elution: 95% ethyl acetate, 5% methanol) gave the title compound (0.051 g, 30% yield) as a white solid.

Workup

  1. temperaturethe reaction mixture was heated to 70° C. for 24 hours
  2. temperatureAfter this time, the reaction mixture was cooled to room temperature
  3. extractionthe mixture was extracted with ethyl acetate (3×10 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. washFlash column chromatography (elution: 95% ethyl acetate, 5% methanol)

Sources & evidence

ORD record
ord-51c2d5f1318546d79bd893bb869f3326
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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