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

HRID 1837053Notes

Reaction equation

HRID 1837053 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[Br:10].[CH2:11]1[C:16](=O)[CH2:15][C:13](=[O:14])[CH2:12]1.[NH2:18][C:19]1[N:23]([CH3:24])[NH:22][C:21](=[O:25])[CH:20]=1>>[Br:10][C:3]1[CH:4]=[C:5]([CH:6]2[C:20]3[C:21](=[O:25])[NH:22][N:23]([CH3:24])[C:19]=3[NH:18][C:16]3[CH2:11][CH2:12][C:13](=[O:14])[C:15]2=3)[CH:8]=[CH:9][C:2]=1[CH3:1]

Participants

4

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 8167653-Bromo-4-methylbenzaldehyde

Product 1

HCID 102927674-(3-Bromo-4-methylphenyl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 60.6%

Procedure

4-Methyl-3-bromobenzaldehyde (0.3 g, 1.5 mmol), prepared as described in (Pearson et al., J. Org. Chem. (1958) 23, 1412-1416), 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 0.34 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.27 (s, 3H), 2.29 (t, 2H), 2.67 (m, 2H), 3.5 (s, 3H), 4.63 (s, 1H), 7.04 (dd, 1H), 7.18 (d, 1H), 7.29 (ds, 1H), 9.51 (bs, 1H), 10.37 (s, 1H); MS (ESI−) m/z 361 (M−H)−; Anal. calcd for C11H16N3BrO2: C, 54.54; H, 4.28; N, 11.23. Found: C, 54.30; H, 4.46; N, 10.94.

Sources & evidence

ORD record
ord-b0c3c173e3d54ec5acd70fd3f028f489
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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