1,3-Cyclohexanedione → HCID 10222157, compound

HRID 1837109Notes

Reaction equation

HRID 1837109 reaction equation
[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[C:19]1(=O)[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH2:20]1>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:20]3[C:21](=[O:25])[CH2:22][CH2:23][CH2:24][C:19]=3[NH:1][C:2]3[N:3]([CH3:8])[O:4][C:5](=[O:7])[C:6]2=3)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 10222157HCID 10222157, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 45A (0.086 g, 0.75 mmol), 3-bromo-4-fluorobenzaldehyde (0.15 g, 0.075 mmol), and 1,3-cyclohexanedione (0.084 g, 0.75 mmol) in ethyl alcohol (2 mL) were heated at 80° C. for 2 days in a sealed tube. The resulting mixture was allowed to cool to ambient temperature and filtered to provide the title compound as the filter cake (0.09 g). 1H NMR (300 MHz, DMSO-d6) δ 1.95 (m, 2H), 2.27 (m, 2H), 2.63 (m, 2H), 3.24 (s, 3H), 4.69 (s, 1H), 7.2 (m, 1H), 7.23 (t, 1H), 7.45 (dd, 1H), 10.2 (s, 1H); MS (ESI) m/z 393 (M−H)−; Anal. Calcd for C17H14N2BrFO3: C, 62.48; H, 3.86; N, 12.86. Found: C, 62.55; H, 4.07; N, 12.61.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-0be70d3c54404af98c5afeba44dff845
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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