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

Participants

Role	Name	HCID	Charge
Reactant	1,3-Cyclopentanedione	HCID 77466	—
Reactant	5-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one	HCID 252198	—
Reactant	4-Bromo-3-chlorobenzaldehyde	HCID 14049806	—
Product	4-(4-Bromo-3-chlorophenyl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dione	HCID 10294056	67.6%

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06538004B2
Source dataset	uspto-grants-2003_03
ORD ID	ord-53dc31871807443383b4a814a5e616c4
Source note	uspto-grants-2003_03