1-Methylpiperazine → HCID 22632981, compound

HRID 2270166Notes

Reaction equation

HRID 2270166 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]([O:15][N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][C:21](F)=[C:22]([F:27])[CH:23]=2)[N:18]([CH2:29][CH3:30])[C:17]1=[O:31])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH2:8]([O:15][N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][C:21]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[C:22]([F:27])[CH:23]=2)[N:18]([CH2:29][CH3:30])[C:17]1=[O:31])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15908876HCID 15908876, compound

Product 1

HCID 22632981HCID 22632981, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methylpiperazine (0.08 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 DBU (0.09 mL, 0.6 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 water 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 0.14 g of the title compound as a solid, mp 134-136° C.

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 water brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-36be5db6e0394c02bad2356e355a2015
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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