2H-pyran-3,5(4H,6H)-dione → HCID 10114240, compound

HRID 1837110Notes

Reaction equation

HRID 1837110 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[I:18].[O:19]1[CH2:24][C:23](=O)[CH2:22][C:21](=[O:26])[CH2:20]1>C(O)C>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[C:22]3[C:21](=[O:26])[CH2:20][O:19][CH2:24][C:23]=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[I:18]

Participants

5

Reactant 3

HCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 103080734-Fluoro-3-iodobenzaldehydeHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 10114240HCID 10114240, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 45A (0.086 g, 0.75 mmol), the product from Example 12C (0.19 g, 0.75 mmol) and 2H-pyran-3,5(4H,6H)-dione (0.085 g, 0.75 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 5% methanol/methylene chloride to provide the title compound (0.03 g). 1H NMR (300 MHz, DMSO-d6) δ 3.23 (s, 3H), 4.06 (s, 2H), 4.58 (q, 2H), 4.72 (s, 1H), 7.18 (t, 1H), 7.25 (m, 1H), 7.63 (dd, 1H), 10.9 (s, 1H); MS (ESI) m/z 441 (M−H)−; Anal. Calcd for C16H12N2FIO4: C, 43.46; H, 2.74; N, 6.34. Found: C, 42.96; H, 2.93; N, 5.98.

Workup

  1. customwas evaporated under reduced pressure
  2. customThe residue was chromatographed
  3. washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-021f9ca6125448bea6977306bbb46bb0
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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