1,3-Cyclopentanedione → 4-[4-Fluoro-3-(2-furyl)phenyl]-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dione

HRID 1837063Notes

Reaction equation

HRID 1837063 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[C:10]1[O:11][CH:12]=[CH:13][CH:14]=1.[CH2:15]1[C:20](=O)[CH2:19][C:17](=[O:18])[CH2:16]1.[NH2:22][C:23]1[N:27]([CH3:28])[NH:26][C:25](=[O:29])[CH:24]=1>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[C:24]3[C:25](=[O:29])[NH:26][N:27]([CH3:28])[C:23]=3[NH:22][C:20]3[CH2:15][CH2:16][C:17](=[O:18])[C:19]2=3)=[CH:4][C:3]=1[C:10]1[O:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 234975044-Fluoro-3-(furan-2-yl)benzaldehyde

Product 1

HCID 99472504-[4-Fluoro-3-(2-furyl)phenyl]-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 73.9%

Procedure

4-Fluoro-3-(2-furyl)-benzaldehyde (0.38 g, 2.0 mmol) from Example 14A, 1,3-cyclopentadione (0.2 g, 2.0 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.22 g, 2.0 mmol) were processed as described in Example 1 to provide 0.54 g of the title compound.

Sources & evidence

ORD record
ord-65e4ab4fdc864a4cb049e83c1124cdb8
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

Loading…