1,3-Cyclohexanedione → HCID 10293018, compound

HRID 1837048Notes

Reaction equation

HRID 1837048 reaction equation
[NH2:1][C:2]1[NH:6][NH:5][C:4](=[O:7])[CH:3]=1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH:12]=O.[C:18]1(=O)[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH2:19]1>>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]2[C:19]3[C:20](=[O:24])[CH2:21][CH2:22][CH2:23][C:18]=3[NH:1][C:2]3[NH:6][NH:5][C:4](=[O:7])[C:3]2=3)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

4

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 962215-Amino-1H-pyrazol-3-olHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 10293018HCID 10293018, compoundYield 24.7%

Procedure

5-Amino-1,2-dihydropyrazol-3-one (0.15 g, 1.5 mmol), 3-bromo-4-fluorobenzaldehyde (0.3 g, 1.5 mmol), and 1,3-cyclohexanedione (0.17 g, 1.5 mmol) were processed as described in Example 2 to provide 0.14 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.85 (m, 2H), 2.18 (m, 2H), 2.55 (m, 2H), 4.94 (s,1H), 7.12 (m, 1H), 718 (t, 1H), 7.4 (dd, 1H), 9.75 (s, 1H), 10.35 (bs, 1H), 11.33 (bs, 1H); MS (ESI−) m/z 376 (M−H)−; Anal. Calcd for C16H13N3BrFO2: C, 50.79; H, 3.44; N, 11.11. Found: C, 50.45; H, 3.42; N, 11.33.

Sources & evidence

ORD record
ord-face6880b13245c7b7c42fd3629e8eba
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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