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

HRID 1862422Notes

Reaction equation

HRID 1862422 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH:10]=O)[CH:7]=[CH:6][C:5]=12.[CH2:12]1[C:17](=O)[CH2:16][C:14](=[O:15])[CH2:13]1.[NH2:19][C:20]1[N:24]([CH3:25])[NH:23][C:22](=[O:26])[CH:21]=1>>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH:10]3[C:21]4[C:22](=[O:26])[NH:23][N:24]([CH3:25])[C:20]=4[NH:19][C:17]4[CH2:12][CH2:13][C:14](=[O:15])[C:16]3=4)[CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 2776296Benzo(c)(1,2,5)oxadiazole-5-carbaldehyde

Product 1

HCID 99669844-(2,1,3-Benzoxadiazol-5-yl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 52.6%

Procedure

2,1,3-Benzoxadiazole-5-carboxaldehyde (0.15 g, 1.0 mmol), prepared as described in (Gasco, A. M., Ermondi, G. Eur. J. Med. Chem., (1996) 31, 3), 1,3cyclopentadione (0.1 g, 1.0 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.11 g, 1.0 mmol) were processed as described in Example 1 to provide 0.17 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.32 (m, 2H), 2.71 (m, 2H), 3.51 (s, 3H), 4.87 (s, 1H), 7.5 (dd, 1H), 7.6 (s, 1H), 7.9 (d, 1H), 9.61 (bs, 1H), 10.52 (s, 1H);

Sources & evidence

ORD record
ord-0dd9792588c74aa8ad3d383ce9b29721
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

Loading…