Acetone, oxime → HCID 54200686, compound

HRID 1839472Notes

Reaction equation

HRID 1839472 reaction equation
CC(=[N:4][OH:5])C.CC(C)([O-])C.[K+].[C:12]([C:14]1[CH:15]=[C:16]([CH:37]=[CH:38][C:39]=1F)[C:17]([NH:19][C:20]1[C:21]([NH:26][C:27](=[O:36])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:18])#[N:13]>CN(C=O)C.C1COCC1>[NH2:13][C:12]1[C:14]2[CH:15]=[C:16]([C:17]([NH:19][C:20]3[C:21]([NH:26][C:27](=[O:36])[C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:18])[CH:37]=[CH:38][C:39]=2[O:5][N:4]=1

Participants

6

Reactant 3

HCID 67180Acetone, oximeHCID 23665647Potassium tert-butoxideHCID 53861570HCID 53861570, compound

Product 1

HCID 54200686HCID 54200686, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of acetone oxime (94 mg, 1.28 mmol) in DMF (2 mL) was added a 1 M solution of potassium t-butoxide (1.28 mL, 1.28 mmol) in THF. After 30 min, N1-(3-cyano-4-fluorobenzoyl)-N2-(4-methoxybenzoyl)-1,2-benzenediamine (100 mg, 0.26 mmol) was added and stirring continued for 72 h. The solvents were removed in vacuo and the residue was dissolved in methanol (20 mL). To this stirring solution was added water (15 mL) and conc HCl (3 mL), and the solution was heated to reflux. After 2 h, the solvents were removed in vacuo and the residue was dissolved in methanol. Silica gel was added and then the solvents were removed in vacuo. This dry pack was loaded onto a silica gel column and eluted with 1:1 ethyl acetate/dichloromethane. The product containing fractions were combined and concentrated to give 48 mg (46%) of white solid.

Workup

  1. waitcontinued for 72 h
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue was dissolved in methanol (20 mL)
  4. additionTo this stirring solution was added water (15 mL) and conc HCl (3 mL)
  5. temperaturethe solution was heated to reflux
  6. waitAfter 2 h
  7. customthe solvents were removed in vacuo
  8. dissolutionthe residue was dissolved in methanol
  9. additionSilica gel was added
  10. customthe solvents were removed in vacuo
  11. washeluted with 1:1 ethyl acetate/dichloromethane
  12. additionThe product containing fractions
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-cb26348d5983482ebb0f8e15d5e2b9f8
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

Loading…