Morpholine → HCID 22632899, compound

HRID 2270165Notes

Reaction equation

HRID 2270165 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([O:14][N:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][C:20](F)=[C:21]([F:26])[CH:22]=2)[N:17]([CH2:28][CH3:29])[C:16]1=[O:30])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(#N)C>[CH2:7]([O:14][N:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][C:20]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[C:21]([F:26])[CH:22]=2)[N:17]([CH2:28][CH3:29])[C:16]1=[O:30])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 15908876HCID 15908876, compound

Product 1

HCID 22632899HCID 22632899, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Morpholine (0.06 mL, 0.72 mmol) was added to a solution of 3-benzyloxy-1-ethyl-6,7-difluoro-1H-quinazoline-2,4-dione (Example C, 0.2 g, 0.6 mmol) and triethylamine (0.17 mL, 1.2 mmol) in 30 mL of acetonitrile. The solution was warmed to reflux for 100 hours, cooled, and concentrated to a solid. The solid was dissolved in chloroform washed with 1N HCl, saturated NaHCO3, brine, and dried over magnesium sulfate. The solution was concentrated to give 0.21 g of a solid. The solid was purified by column chromatography (chloroform/methanol 99:1). The appropriate fractions were combined to give 0.17 g of the title compound as a solid.

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux for 100 hours
  3. temperaturecooled
  4. concentrationconcentrated to a solid
  5. dissolutionThe solid was dissolved in chloroform
  6. washwashed with 1N HCl, saturated NaHCO3, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-0a9ff6ca53954c379ebeec01573e8a70
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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