Triethylamine → HCID 22632920, compound

HRID 2416859Notes

Reaction equation

HRID 2416859 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([O:9][N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15](F)=[C:16]([F:21])[CH:17]=2)[N:12]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]1=[O:30])[CH:7]=[CH2:8].C(N(CC)CC)C>C(#N)C>[CH2:6]([O:9][N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:16]([F:21])[CH:17]=2)[N:12]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:11]1=[O:30])[CH:7]=[CH2:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 22632888HCID 22632888, compound

Product 1

HCID 22632920HCID 22632920, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyrrolidine (0.04 mL, 0.52 mmol) was added to a solution of 3-allyloxy-1-benzyl-6,7-difluoro-1H-quinazoline-2,4-dione (Example A-4, 0.15 g, 0.4 mmol) and triethylamine (0.12 mL, 0.9 mmol) in 15 mL of acetonitrile. The solution was warmed to reflux for 17 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 0.15 g of the title compound as a solid, mp 148-150° C.

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux for 17 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-4b3558be4b134ec9b876acae2d74b712
Source dataset
uspto-grants-2004_11
Patent number
US06825199B2

Reaction notes

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