1,3-Cyclohexanedione → HCID 10293886, compound

HRID 1837067Notes

Reaction equation

HRID 1837067 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[C:11]1(=[O:18])[CH2:16][CH2:15][CH2:14][C:13](=O)[CH2:12]1.[NH2:19][C:20]1[N:24]([CH3:25])[NH:23][C:22](=[O:26])[CH:21]=1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:12]3[C:11](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]=3[NH:19][C:20]3[N:24]([CH3:25])[NH:23][C:22](=[O:26])[C:21]2=3)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

4

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one

Product 1

HCID 10293886HCID 10293886, compoundYield 68.8%

Procedure

3-Bromo-4-fluorobenzaldehyde (0.2 g, 1.0 mmol), 1,3-cyclohexanedione (0.11 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 I to provide 0.27 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.9 (m, 2H), 2.2 (m, 2H), 2.6 (m, 2H), 3.45 (s, 3H), 4.88 (s, 1H), 7.12 (m, 1H), 7.18 (t, 1H), 7.38 (dd, 1H), 9.53 (s, 1H), 9.72 (s, 1H); MS (ESI−) m/z 390 (M−H)−; Anal. Calcd for C11H15N3BrFO2.C2H6O: C, 52.06; H, 4.61; N, 9.85. Found: C, 51.72; H, 4.56; N, 7.98.

Sources & evidence

ORD record
ord-ea92493d6c0d474d8d37914dae29d101
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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