p-(Trifluoromethoxy)benzaldehyde → 1-Methyl-4-[4-(trifluoromethoxy)phenyl]-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dione

HRID 1837052Notes

Reaction equation

HRID 1837052 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[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>>[CH3:27][N:26]1[C:22]2[NH:21][C:19]3[CH2:14][CH2:15][C:16](=[O:17])[C:18]=3[CH:8]([C:7]3[CH:10]=[CH:11][C:4]([O:3][C:2]([F:13])([F:12])[F:1])=[CH:5][CH:6]=3)[C:23]=2[C:24](=[O:28])[NH:25]1

Participants

4

Reactant 3

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 774661,3-CyclopentanedioneHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one

Product 1

HCID 101334161-Methyl-4-[4-(trifluoromethoxy)phenyl]-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 27.4%

Procedure

4-Trifluoromethoxybenzaldehyde (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 0.15 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.3 (t, 2H), 2.68 (m, 2H), 3.49 (s, 3H), 4.72 (s, 1H), 7.18 (d, 2H), 7.23 (d, 2H), 9.5 (bs, 1H) 10.37 (s, 1H); MS (ESI−) m/z 364 (M−H)−; Anal. calcd for C17H14N3F3O3·0.25 H2O: C, 55.21; H, 3.95; N, 11.36. Found: C, 55.34; H, 3.78; N, 10.97.

Sources & evidence

ORD record
ord-5291f4b64b5a402885c9b4c96cd274fd
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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