1,3-Cyclopentanedione → HCID 9925263, compound

HRID 1837047Notes

Reaction equation

HRID 1837047 reaction equation
[NH2:1][C:2]1[NH:6][NH:5][C:4](=[O:7])[CH:3]=1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH:12]=O.[C:18]1(=O)[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]1>C(O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]2[C:3]3[C:4](=[O:7])[NH:5][NH:6][C:2]=3[NH:1][C:18]3[CH2:22][CH2:21][C:20](=[O:23])[C:19]2=3)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

5

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 962215-Amino-1H-pyrazol-3-olHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 9925263HCID 9925263, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Amino-1,2-dihydropyrazol-3-one (0.15 g, 1.5 mmol), 3-bromo-4-fluorobenzaldehyde (0.31 g, 1.5 mmol), and 1,3-cyclopentanedione (0.15 g, 1.5 mmol) in ethyl alcohol (3 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction mixture was evaporated under reduced pressure and the residue was chromatographed on silica gel eluting with ethyl acetate:formic acid:water (18:1:1) to provide 0.125 g of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 2.22 (t, 2H), 2.61 (m, 2H), 4.73 (s,1H), 7.15 (m, 1H), 7.2 (m, 1H), 7.4 (dd, 1H), 9.75 (s, 1H), 10.21 (s, 1H), 11.3 (bs, 1H); MS (ESI) m/z 362 (M−H)−; Anal. calcd for C15H, N3BrFO2.0.5H2O: C, 48.28; H, 3.24; N, 11.26Found: C, 48.88; H, 3.29; N, 10.83.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe residue was chromatographed on silica gel eluting with ethyl acetate:formic acid:water (18:1:1)

Sources & evidence

ORD record
ord-c4589ecf27ba4efdb5305c4e8e4cac6f
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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