HCID 12244509, compound → HCID 56982119, compound

HRID 1839463Notes

Reaction equation

HRID 1839463 reaction equation
CC(C)([O-])C.[K+].Cl.CC(=[N:11][OH:12])C.F[C:14]1[C:39]([C:40]#[N:41])=[CH:38][CH:37]=[CH:36][C:15]=1[C:16]([NH:18][C:19]1[C:20]([NH:25][C:26](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:17]>CN(C=O)C>[NH2:41][C:40]1[C:39]2[CH:38]=[CH:37][CH:36]=[C:15]([C:16]([NH:18][C:19]3[C:20]([NH:25][C:26](=[O:35])[C:27]4[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=4)=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:17])[C:14]=2[O:12][N:11]=1

Participants

5

Reactant 3

HCID 12244509HCID 12244509, compound2×HCID 23665647Potassium tert-butoxide2×HCID 54109064HCID 54109064, compound

Product 1

HCID 56982119HCID 56982119, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of potassium t-butoxide (92 mg, 0.82 mmol) in DMF (5 mL) was added acetone oxime hydrochloride (60 mg, 0.82 mmol). After 1 h, N1-(2-fluoro-3-cyanobenzoyl)-N2-(4-methoxybenzoyl)-1,2-benzenediamine (290 mg, 0.74 mmol) was added. After another 2 h, potassium t-butoxide (92 mg, 0.82 mmol) and acetone oxime hydrochloride (60 mg, 0.82 mmol) were added. After 12 h, the reaction was concentrated and the residue was dissolved in ethyl acetate and washed with water (2×), brine, MgSO4 dried, and concentrated. The resulting solid was dissolved in ethanol (35 mL), 5% HCl (35 mL) was added, and the mixture was refluxed for 1 h. The reaction was cooled, concentrated to 2 mL, diluted with ethyl acetate (250 mL), and neutralized with satd aq NaHCO3. The organic layer was washed with satd aq NaHCO3 (2×) and brine, MgSO4 dried, concentrated and crystallized to give the title compound as an off-white solid (106 mg, 35%); MS(FD): 402.1.

Workup

  1. waitAfter another 2 h
  2. waitAfter 12 h
  3. concentrationthe reaction was concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with water (2×), brine, MgSO4
  6. customdried
  7. concentrationconcentrated
  8. dissolutionThe resulting solid was dissolved in ethanol (35 mL)
  9. addition5% HCl (35 mL) was added
  10. temperaturethe mixture was refluxed for 1 h
  11. temperatureThe reaction was cooled
  12. concentrationconcentrated to 2 mL
  13. additiondiluted with ethyl acetate (250 mL)
  14. washThe organic layer was washed with satd aq NaHCO3 (2×) and brine, MgSO4
  15. customdried
  16. concentrationconcentrated
  17. customcrystallized

Sources & evidence

ORD record
ord-bd2e09383c0d49688fd28cc7d2db5b6f
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

Loading…