Acetone → HCID 57527199, compound

HRID 1671810Notes

Reaction equation

HRID 1671810 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH2:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[N:23][C:18]3=[CH:17][CH:16]=2)SCCCS1.CC(C)=[O:30].CC1C=CC(S(O)(=O)=O)=CC=1.O>CO.O.Cl[Hg]Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:30])[CH2:14][C:15]1[N:20]=[C:19]2[S:21][C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[N:23][C:18]2=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 57527158HCID 57527158, compound

Product 1

HCID 57527199HCID 57527199, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 24085Mercuric ChlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 5-((2-(2-fluorophenyl)-1,3-dithian-2-yl)methyl)-N-isopropylthiazolo[5,4-b]pyridin-2-amine (0.61 g, 1.45 mmol, 1.0 eq.) in MeOH (73 mL) and water (6 mL) were added HgO (0.83 g, 3.83 mmol, 2.6 eq.) and HgCl2 (1.83 g, 6.74 mmol, 4.6 eq.). After stirring for 15 min., the solution was refluxed for another 15 min. and cooled to room temperature. The precipitate was removed, and the filtrate was concentrated in vacuo. The residue was diluted with EtOAc and water, and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. Acetone (7 mL), water (0.1 mL, 5.56 mmol, 3.8 eq.), and TsOH.H2O (0.0342 g, 0.180 mmol, 0.1 eq.) were added, and the reaction was stirred overnight and concentrated in vacuo. The residue was diluted with CH2Cl2 and water, and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography using CH2Cl2:MeOH (15:0.1) as eluent afforded 1-(2-fluorophenyl)-2-(2-(isopropylamino)thiazolo[5,4-b]pyridin-5-yl)ethanone as a yellow solid (0.1994 g, 42% yield).

Workup

  1. temperaturethe solution was refluxed for another 15 min.
  2. customThe precipitate was removed
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with EtOAc and water
  5. customthe layers were separated
  6. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. stirringthe reaction was stirred overnight
  11. concentrationconcentrated in vacuo
  12. additionThe residue was diluted with CH2Cl2 and water
  13. customthe layers were separated
  14. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  15. dry with materialdried over Na2SO4
  16. filtrationfiltered
  17. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7dd16231ba70479da8affe94e51fbaa8
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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