Water → HCID 68980406, compound

HRID 1783718Notes

Reaction equation

HRID 1783718 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([Br:18])=[N:13][N:12]([CH:19]([CH3:21])[CH3:20])[C:11]2=[O:22])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:27][CH2:28]OC.O.[CH3:32][N:33](C=O)[CH3:34]>>[C:1]([O:5][C:6](=[O:23])[N:7]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([Br:18])=[N:13][N:12]([CH:19]([CH3:20])[CH3:21])[C:11]2=[O:22])[CH2:27][CH2:28][N:33]([CH3:34])[CH3:32])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 68896332HCID 68896332, compound

Product 1

HCID 68980406HCID 68980406, compoundYield 23%

Procedure

(1-Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-6-yl)-carbamic acid tert-butyl ester (0.75 g, 1.96 mmol) was dissolved in DMF (10 ml). To this was added NaH (60%, 0.2 g, 4.9 mmol) as a suspension in DMF (5 ml). The mixture was stirred at RT for 30 min then 1-bromo-2-methoxyethane (0.4 g, 2.9 mmol) was added in one portion as a solution in DMF (5 ml) and the reaction mixture was stirred at RT for 3 hours. After this time, the reaction mixture was cooled to RT and water (20 ml) was added cautiously, the mixture was extracted with EtOAc (3×50 ml), the organic layers were combined, dried (MgSO4), filtered, concentrated under vacuum and the residue subjected to flash column chromatography (elution: 60% heptane, 40% EtOAc) to afford (1-bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-6-yl)-(2-dimethylamino-ethyl)-carbamic acid tert-butyl ester (0.2 g, 23% yield) as a white solid.

Workup

  1. stirringthe reaction mixture was stirred at RT for 3 hours
  2. temperatureAfter this time, the reaction mixture was cooled to RT
  3. extractionthe mixture was extracted with EtOAc (3×50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. washthe residue subjected to flash column chromatography (elution: 60% heptane, 40% EtOAc)

Sources & evidence

ORD record
ord-b38392a43aac4f7f825e10b1356bb2ff
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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