1,3-Cyclohexanedione, 4,4-dimethyl- → 4-[4-fluoro-3-(2-furyl)phenyl]-1,6,6-trimethyl-4,7,8,9-tetrahydro-1H-pyrazolo[3,4-b]quinoline-3,5(2H,6H)-dione

HRID 1837073Notes

Reaction equation

HRID 1837073 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[CH:3]=1.[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[C:18]1[O:19][CH:20]=[CH:21][CH:22]=1.[CH3:23][C:24]1([CH3:32])[CH2:29][CH2:28][C:27](=O)[CH2:26][C:25]1=[O:31]>>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[C:26]3[C:25](=[O:31])[C:24]([CH3:32])([CH3:23])[CH2:29][CH2:28][C:27]=3[NH:1][C:2]3[N:6]([CH3:7])[NH:5][C:4](=[O:8])[C:3]2=3)=[CH:12][C:11]=1[C:18]1[O:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 1363601,3-Cyclohexanedione, 4,4-dimethyl-HCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 234975044-Fluoro-3-(furan-2-yl)benzaldehyde

Product 1

HCID 102230864-[4-fluoro-3-(2-furyl)phenyl]-1,6,6-trimethyl-4,7,8,9-tetrahydro-1H-pyrazolo[3,4-b]quinoline-3,5(2H,6H)-dioneYield 68.7%

Procedure

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.11 g, 1 mmol), 4-fluoro-3-(2-furyl)-benzaldehyde (0.19 g, 1 mmol), and 4,4-dimethyl-1,3-cyclohexanedione (0.14 g, 1 mmol) were processed as described in Example 22 to provide 0.28 g (67%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.92 (s, 3H), 0.99 (s, 3H), 1.78 (t, 2H), 2.65 (m, 2H), 3.45 (s, 3H), 4.88 (s, 1H), 6.62 (m, 1H), 6.76 (m, 1H), 7.06 (m, 1H), 7.1 (t, 1H), 7.55 (dd, 1H), 7.81 (dd, 1H), 9.49 (s, 1H), 9.6 (s, 1H); MS (ESI−) m/z 406 (M−H)−; Anal. calcd for C23H22N3FO3: C, 67.80; H, 5.40; N, 10.3. Found: C, 68.05; H, 5.39; N, 10.25.

Sources & evidence

ORD record
ord-b6af744b265943158e2a74f5206786d6
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

Loading…