Triethylamine → HCID 68552826, compound

HRID 2189923Notes

Reaction equation

HRID 2189923 reaction equation
O=[C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].Cl.[F:20][C:21]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:22]=1[C:23](=[S:26])[NH:24][NH2:25].C(N(CC)CC)C>CCO>[F:20][C:21]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:22]=1[C:23]1[S:26][C:2]([CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:25][N:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17818960tert-Butyl (3-oxo-3-phenylpropyl)carbamateHCID 78358145HCID 78358145, compound

Product 1

HCID 68552826HCID 68552826, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a cooled (0° C.) solution of tert-butyl 3-oxo-3-phenylpropylcarbamate (0.68 g, 2.73 mmol) and 2,5-difluorobenzothiohydrazide hydrochloride (0.613 g, 2.73 mmol) in EtOH (27 mL) was added triethylamine (0.57 mL, 4.09 mmol). After stirring at room temperature for 8 hours, the mixture was heated to 65° C. for 16 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (100 mL). The solution was washed with water and brine (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed (30% ethyl acetate in hexanes) to provide the crude product as a brown syrup which was used directly in the next step.

Workup

  1. temperaturethe mixture was heated to 65° C. for 16 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  4. washThe solution was washed with water and brine (40 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c63fc19e878f4ca095abbc1fc082e9e3
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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