1,3-Cyclohexanedione, 4,4-dimethyl- → HCID 10202275, compound

HRID 1837071Notes

Reaction equation

HRID 1837071 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[CH3:19][C:20]1([CH3:28])[CH2:25][CH2:24][C:23](=O)[CH2:22][C:21]1=[O:27]>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:22]3[C:21](=[O:27])[C:20]([CH3:28])([CH3:19])[CH2:25][CH2:24][C:23]=3[NH:1][C:2]3[N:6]([CH3:7])[NH:5][C:4](=[O:8])[C:3]2=3)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

5

Reactant 3

HCID 1363601,3-Cyclohexanedione, 4,4-dimethyl-HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one

Product 1

HCID 10202275HCID 10202275, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.23 g, 2 mmol), 3-bromo-4-fluorobenzaldehyde (0.4 g, 2 mmol), and 4,4-dimethyl-1,3-cyclohexanedione (0.28 g, 2 mmol) in ethyl alcohol (3 mL) were heated at 80° C. in a sealed tube for 2 days. The reaction mixture was cooled and the resulting precipitate was filtered off and washed with ethyl acetate to provide 0.55 g of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 0.92 (s, 3H), 0.98 (s, 3H), 1.78 (t, 2H), 2.63 (m, 2H), 3.43 (s, 3H), 4.83 (s, 1H), 7.11 (m, 1H), 7.17 (t, 1H), 7.33 (dd, 1H), 9.53 (s, 1H), 9.66 (s, 1H); MS (ESI−) m/z 420 (M−H)−; Anal. calcd for C19H19N3BrFO2: C, 54.30; H, 4.56; N, 10.00. Found: C, 54.29; H, 4.61; N, 9.97.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe resulting precipitate was filtered off
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-c67fe7f2e5054e1d89029127eb0f4c59
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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