1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178517379, compound

HRID 1851152Notes

Reaction equation

HRID 1851152 reaction equation
S(O)(O)(=O)=O.[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH2:11].[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]([C:25](OCC)=[O:26])[C:20](OCC)=[O:21].N12CCCN=C1CCCCC2>CN(C=O)C>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[C:25]([OH:26])=[N:11][C:7]2[N:6]([CH:10]=[CH:9][N:8]=2)[C:20]=1[OH:21]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 22325508HCID 22325508, compound

Product 1

HCID 178517379HCID 178517379, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5 g (27.5 mmol) 1H-Imidazol-2-ylamine sulfate are dissolved in 31.7 mL DMF. 7 g (27.5 mmol) diethyl (2-fluorophenyl)malonate are added. After dropwise addition of 12.3 mL (82.6 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene the reaction mixture is stirred at 100° C. over night. The DMF is evaporated and the darkbrown oily residue treated with 150 mL water (complete dissolution). 2M HCl (60 mL) is added at room temperature until a pH of 1. After stirring for 1 h at ice bath cooling the formed crystals are collected by filtration to yield the product (3.43 g=48.3%), which is used without further purification. Another crop of 0.41 g (6.1%) is obtained by evaporating the solvent, treating the oily residue with water and 2M HCl. After stirring for five hours the crystals are collected and washed with water.

Workup

  1. customThe DMF is evaporated
  2. additionthe darkbrown oily residue treated with 150 mL water (complete dissolution)
  3. addition2M HCl (60 mL) is added at room temperature until a pH of 1
  4. stirringAfter stirring for 1 h at ice bath
  5. temperaturecooling the formed crystals
  6. filtrationare collected by filtration
  7. customto yield the product (3.43 g=48.3%), which
  8. customis used without further purification
  9. customAnother crop of 0.41 g (6.1%) is obtained
  10. customby evaporating the solvent
  11. additiontreating the oily residue with water and 2M HCl
  12. stirringAfter stirring for five hours the crystals
  13. customare collected
  14. washwashed with water

Sources & evidence

ORD record
ord-f725598f884b4ce4beedf3599ce2b0eb
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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