Water → HCID 21106564, compound

HRID 1783664Notes

Reaction equation

HRID 1783664 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=O)C>[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 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 RT for 30 min then 4-(2-chloro-ethyl)-morpholine (0.12 g, 0.66 mmol) was added in one portion as a solution in DMF (I ml) and the reaction mixture was heated to 70° C. for 24 hours. After this time, the reaction mixture was cooled to RT and 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: 95% EtOAc, 5% MeOH) gave the title compound (0.051 g, 30% yield) as a white solid. 1H-NMR: (400 MHz, CDCl3), 7.72 (1H, d), 7.49 (1H, s), 7.16 (1 H, d), 5.42-5.29 (1H, m), 3.73-3.67 (4H, m), 3.66-3.59 (2H, t), 3.15 (3H, s), 2.61-2.54 (2H, m), 2.53-2.46 (4H, m), 1.41 (6H, d).

Workup

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

Sources & evidence

ORD record
ord-aef2170197764f63b3a6bd3bcd78ba7e
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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