1,3-Cyclopentanedione → HCID 10271045, compound

HRID 1862456Notes

Reaction equation

HRID 1862456 reaction equation
[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[C:19]1(=O)[CH2:23][CH2:22][C:21](=[O:24])[CH2:20]1>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:6]3[C:5](=[O:7])[O:4][N:3]([CH3:8])[C:2]=3[NH:1][C:19]3[CH2:23][CH2:22][C:21](=[O:24])[C:20]2=3)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

5

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 10271045HCID 10271045, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 45A (0.11 g, 1 mmol), 3-bromo-4-fluorobenzaldehyde (0.2 g, 1 mmol), and 1,3-cyclopentanedione (0.1 g, 1 mmol) in ethyl alcohol (2 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction mixture was allowed to cool to ambient temperature and was evaporated under reduced pressure. The residue was chromatographed eluting with 19:0.5:0.5 ethylacetate:formic acid: water to provide the title compound (0.07 g). 1H NMR (300 MHz, DMSO-d6) δ 2.35 (t, 2H), 2.72 (m, 2H), 3.29 (s, 3H), 4.6 (s, 1H), 7.23 (d, 2H), 7.5 (d, 1H) 11.0 (s, 1H); MS (ESI) m/z 379 (M−H)−; Anal. Calcd for C16H12N3FBrO3: C, 50.68;H, 3.19; N, 7.39. Found: C, 50.34;H, 3.20; N, 7.34.

Workup

  1. customwas evaporated under reduced pressure
  2. customThe residue was chromatographed
  3. washeluting with 19:0.5:0.5 ethylacetate

Sources & evidence

ORD record
ord-cb6ead0b10814f769025ab266646ad27
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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