1,3-Cyclohexanedione → HCID 178428409, compound

HRID 408552Notes

Reaction equation

HRID 408552 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[CH3:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16](/[CH:19]=[C:20](/[C:23](=O)[CH3:24])\[C:21]#[N:22])[CH:17]=2)[NH:12][N:11]=1.C([O-])(=O)C.[NH4+:30]>C(O)(=O)C>[CH3:24][C:23]1[NH:30][C:3]2[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[C:2]=2[CH:19]([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[C:10]3[CH3:9])[C:20]=1[C:21]#[N:22]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 517165Ammonium Acetate2×HCID 178467936HCID 178467936, compound

Product 1

HCID 178428409HCID 178428409, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

273 mg (2.442 mmol) cyclohexane-1,3-dione, 500 mg (2.222 mmol) (2E)-2-[(3-methyl-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 2A) and 205 mg (2.664 mmol) ammonium acetate in acetic acid (5 ml) were heated to 50° C. overnight. Then, additional ammonium acetate (102 mg, 1.332 mmol) was added, and the mixture was heated to reflux for 24 h. After cooling, the mixture was evaporated to dryness, and the residue was taken up in ethyl acetate and washed with water twice. The combined aqueous phases were extracted with ethyl acetate. The organic layers were combined and dried over sodium sulfate. After filtration and evaporation to dryness, the remaining solid was purified by preparative RP-HPLC (acetonitrile/water gradient) to yield 55 mg (8% of th.) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 h
  3. temperatureAfter cooling
  4. customthe mixture was evaporated to dryness
  5. washwashed with water twice
  6. extractionThe combined aqueous phases were extracted with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtration and evaporation to dryness
  9. customthe remaining solid was purified by preparative RP-HPLC (acetonitrile/water gradient)

Sources & evidence

ORD record
ord-358df9841ff74b40b473d1cec60cef24
Source dataset
uspto-grants-2014_06
Patent number
US08759341B2

Reaction notes

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