1-(Thiazol-2-yl)piperazine → HCID 54396548, compound

HRID 1859016Notes

Reaction equation

HRID 1859016 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])[O:10]1.Cl([O-])(=O)(=O)=O.[Li+].[N:25]1([C:31]2[S:32][CH:33]=[CH:34][N:35]=2)[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:10])([C@H:11]([N:28]1[CH2:29][CH2:30][N:25]([C:31]2[S:32][CH:33]=[CH:34][N:35]=2)[CH2:26][CH2:27]1)[CH3:12])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1

Participants

5

Reactant 3

HCID 9118061-(Thiazol-2-yl)piperazineHCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 23665649Lithium perchlorate

Product 1

HCID 54396548HCID 54396548, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane IV (502 mg, 2 mmol) and lithium perchlorate (320 mg, 3 mmol) in acetonitrile (10 ml), 2-(piperazin-1-yl)thiazole (X)(507 mg, 3 mmol) was added. The resulting mixture was heated under reflux for 48 h. The reaction mixture was cooled, concentrated under reduced pressure. The residue was disolved in chloroform, washed with water, brine, dried (Na2SO4) and concentrated. The resulting product was purified on a column of silica gel using ethyl acetate and hexane (4:1) as eluent to give the title compound as colorless solid (650 mg, 77%).

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 48 h
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated under reduced pressure
  6. washwashed with water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe resulting product was purified on a column of silica gel

Sources & evidence

ORD record
ord-adf3124eaafd4c7da2c940b35697c504
Source dataset
uspto-grants-2000_11
Patent number
US06153616

Reaction notes

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