HCID 17877358, compound → HCID 17877362, compound

HRID 1599426Notes

Reaction equation

HRID 1599426 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[N:13]=[C:14]2[C:23](=[O:24])[NH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[N:15]2[C:29]=1[CH2:30][C:31]1[NH:32][CH:33]=[CH:34][N:35]=1)=O)C>O1CCCC1>[OH:9][CH2:10][C:12]1[N:13]=[C:14]2[C:23](=[O:24])[NH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:25]([F:28])([F:26])[F:27])[CH:20]=3)[N:15]2[C:29]=1[CH2:30][C:31]1[NH:32][CH:33]=[CH:34][N:35]=1

Participants

4

Reactant 2

HCID 17877358HCID 17877358, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 17877362HCID 17877362, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of lithium aluminium hydride (400 mg, 10.5 mmol) in dry tetrahydrofuran (200 ml) was added 2-ethoxycarbonyl-1-(1-imidazolylmethyl)-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one (3.6 g, 8.8 mmol) in small portions. After 20 min. at 25° C. the temperature was raised to reflux for 2 h. The reaction mixture was cooled to room temperature, quenched with water and then filtered, The solvent was evaporated in vacuo and the residue dissolved in 20% sulphuric acid. The precipitate was filtered off and the liquid phase added potassium hydroxide to pH 11. The product was isolated by continuous liquid/liquid extraction (ethyl acetate) overnight to give 2.1 g (67%) of the title compound. M.p. 215° C.

Workup

  1. temperatureto reflux for 2 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with water
  4. filtrationfiltered
  5. customThe solvent was evaporated in vacuo
  6. dissolutionthe residue dissolved in 20% sulphuric acid
  7. filtrationThe precipitate was filtered off
  8. additionthe liquid phase added potassium hydroxide to pH 11
  9. customThe product was isolated by continuous liquid/liquid extraction (ethyl acetate) overnight

Sources & evidence

ORD record
ord-541bee3e3017421bbeba37ebf72d5fb8
Source dataset
uspto-grants-1998_04
Patent number
US05741785

Reaction notes

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