Dimethyl Sulfoxide → HCID 67549439, compound

HRID 1352372Notes

Reaction equation

HRID 1352372 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]([CH:19]=[C:20]([F:22])[F:21])=[CH:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(C)=O.O.[F-:28].[K+]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[S:15][C:16]([CH2:19][C:20]([F:28])([F:21])[F:22])=[CH:17][N:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 522689Potassium FluorideHCID 675495474-[5-(2,2-Difluoro-vinyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67549439HCID 67549439, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1.03 mmol 4-[5-(2,2-difluoro-vinyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester in 7.5 dimethylsulphoxide and 0.3 ml water was added 7.18 mmol potassium fluoride and the mixture was heated at 120° C. for 2 h. The mixture was then diluted with ethyl acetate and washed sequentially with water and brine. The organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as a yellow crystalline solid (yield 90%). MS (m/e): 352.3 (M+H+, 100%).

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (SiO2, ethyl acetate/heptane)

Sources & evidence

ORD record
ord-e2e8184833a843ec87e288fc2f164793
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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