2H-pyran-3,5(4H,6H)-dione → 4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-4,9-dihydro-1H-isoxazolo[3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

HRID 1837105Notes

Reaction equation

HRID 1837105 reaction equation
[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[C:18]([F:21])([F:20])[F:19].[O:22]1[CH2:27][C:26](=O)[CH2:25][C:24](=[O:29])[CH2:23]1>C(O)C>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[C:25]3[C:24](=[O:29])[CH2:23][O:22][CH2:27][C:26]=3[NH:1][C:2]3[N:3]([CH3:8])[O:4][C:5](=[O:7])[C:6]2=3)=[CH:12][C:11]=1[C:18]([F:21])([F:20])[F:19]

Participants

5

Reactant 3

HCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 5222694-Fluoro-3-(trifluoromethyl)benzaldehydeHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 101568394-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-4,9-dihydro-1H-isoxazolo[3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 45A (0.11 g, 1 mmol), 4-fluoro-3-trifluromethylbenzaldehyde and 2H-pyran-3,5(4H,6H)-dione (0.11 g, 1 mmol) were heated in 2 mL of ethanol for 2 days. The reaction mixture was evaporated under reduced pressure and the remaining residue was triturated with methylene chloride. The resulting precipitate was filtered to provide the title compound as the filter cake. 1H NMR (300 MHz, DMSO-d6) δ 3.28 (s, 3H), 4.07 (s, 2H), 4.58 (q, 2H), 4.87 (s, 1H), 7.42 (t, 1H), 7.59 (m, 2H), 10.8 (s, 1H); MS (ESI) m/z 383 (M−H)−; Anal. Calcd for C16H12N2F4O4: C, 51.61; H, 3.22; N, 7.52. Found: C, 51.09; H, 3.11; N, 6.98.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe remaining residue was triturated with methylene chloride
  3. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-fdea4cca02a445eab620436430a3a202
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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