Dimethylformamide → HCID 18510765, compound

HRID 1370269Notes

Reaction equation

HRID 1370269 reaction equation
ClN1CC(=[O:7])CC1=O.[N:9]1[CH:14]=[C:13](C=O)[CH:12]=[N:11]C=1.[C:17]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:35])[CH:33]=[CH2:34])=[CH:27][CH:26]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.C[N:44]([CH:46]=O)[CH3:45]>N1C=CC=CC=1>[C:17]([C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32]([CH:33]2[O:7][N:11]=[C:12]([C:13]3[CH:45]=[N:44][CH:46]=[N:9][CH:14]=3)[CH2:34]2)=[O:35])=[CH:29][CH:30]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2761034Pyrimidine-5-carboxaldehydeHCID 13586806HCID 13586806, compound2×HCID 14146482N-(4-Benzoylphenyl)prop-2-enamide

Product 1

HCID 18510765HCID 18510765, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

1-Chloro-2,4-pyrrolidinedione (0.011 mol; 98%) was added portionwise to a solution of 5-pyrimidinecarboxaldehyde, oxime (0.036 mol) in DMF (50 ml) and this mixture was heated to 50° C. to start the reaction. The mixture was cooled to RT. Pyridine (0.28 ml) was added. The rest of 1-chloro-2,4-pyrrolidinedione (0.043 mol) was added portionwise and the mixture was stirred for 3 hours at RT. N-(4-benzoylphenyl)propenamide (0.025 mol) was added. Triethylamine (0.053 mol) was added dropwise and the resulting reaction mixture was stirred overnight at RT. The crude mixture was washed with water, then extracted with EtOAc. The organic layer was separated, and the solvent was evaporated. The residue was washed with water and extracted with CH2Cl2. The separated organic layer was dried (Na2SO4), filtered and the solvent was evaporated. The residue was crystallized from CH3OH, washed with diethyl ether and hot CH2Cl2, dried and repurified by HPLC over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and the solvent was evaporated, yielding 3.5 g of (±)-N-(4-benzoylphenyl)-4,5-dihydro-3-(5-pyrimidinyl)-5-isoxazolecarboxamide (compound 349)

Workup

  1. customthe reaction
  2. temperatureThe mixture was cooled to RT
  3. customthe resulting reaction mixture
  4. stirringwas stirred overnight at RT
  5. washThe crude mixture was washed with water
  6. extractionextracted with EtOAc
  7. customThe organic layer was separated
  8. customthe solvent was evaporated
  9. washThe residue was washed with water
  10. extractionextracted with CH2Cl2
  11. dry with materialThe separated organic layer was dried (Na2SO4)
  12. filtrationfiltered
  13. customthe solvent was evaporated
  14. customThe residue was crystallized from CH3OH
  15. washwashed with diethyl ether and hot CH2Cl2
  16. customdried
  17. customrepurified by HPLC over silica gel (eluent: CH2Cl2/CH3OH 97/3)
  18. customThe pure fractions were collected
  19. customthe solvent was evaporated

Sources & evidence

ORD record
ord-34905012734f4411a6a91b4ace8eadb3
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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