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

HRID 1862440Notes

Reaction equation

HRID 1862440 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[CH:3]=1.[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[Cl:18].[C:19]1(=O)[CH2:23][CH2:22][C:21](=[O:24])[CH2:20]1>>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[C:3]3[C:4](=[O:8])[NH:5][N:6]([CH3:7])[C:2]=3[NH:1][C:19]3[CH2:23][CH2:22][C:21](=[O:24])[C:20]2=3)=[CH:12][C:11]=1[Cl:18]

Participants

4

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 140498064-Bromo-3-chlorobenzaldehyde

Product 1

HCID 102940564-(4-Bromo-3-chlorophenyl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 67.6%

Procedure

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.84 g, 0.75 mmol), 4bromo-3-chlorobenzaldehyde (0.157 g, 0.75 mmol) from Example 40C, and 1,3-cyclopentanedione (0.074 g, 0.75 mmol) was processed as described in Example 1 to provide 0.20 g of the title compound. 1H NMR (DMSO-d6) δ 2.29 (t, 2H), 2.68 (m, 2H), 3.49 (s, 3H), 4.69 (s, 1H), 7.02 (dd, 1H), 7.33 (d, 1H), 7.6 (d, 1H), 9.55 (s, 1H), 10.41 (s, 1H); MS (ESI−) m/z 394 (M−H)−; Anal. Calcd for C16H13N3BrClO2: C, 48.66;H, 3.29; N, 10.64. Found: C, 48.92;H, 3.13; N, 10.72.

Sources & evidence

ORD record
ord-53dc31871807443383b4a814a5e616c4
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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