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

HRID 1837054Notes

Reaction equation

HRID 1837054 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH2:14]1[C:19](=O)[CH2:18][C:16](=[O:17])[CH2:15]1.[NH2:21][C:22]1[N:26]([CH3:27])[NH:25][C:24](=[O:28])[CH:23]=1>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[C:23]3[C:24](=[O:28])[NH:25][N:26]([CH3:27])[C:22]=3[NH:21][C:19]3[CH2:14][CH2:15][C:16](=[O:17])[C:18]2=3)=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11]

Participants

4

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 5222694-Fluoro-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 101095204-[4-Fluoro-3-(trifluoromethyl)phenyl]-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 63.5%

Procedure

4-Fluoro-3-trifluoromethylbenzaldehyde (0.28 g, 1.5 mmol), 1,3-cyclopentadione (0.15 g, 1.5 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.17 g, 1.5 mmol) were processed as described in Example 1 to provide 0.35 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.21 (m, 2H), 2.7 (m, 2H), 3.51 (s, 3H), 4.8 (s, 1H), 7.35 (t, 1H), 7.45 (m, 1H), 7.55 (d, 1H), 9.6 (bs, 1H), 10.48 (s, 1H); MS (ESI−) m/z 366 (M−H)−; Anal. calcd for C17H13N3F4O2: C, 55.59; H, 3.51; N, 11.44. Found: C, 55.41; H, 3.37; N, 11.21.

Sources & evidence

ORD record
ord-dc512179b9a64cc49b925d445ef85024
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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