Trifluoroacetic acid → HCID 86591035, compound

HRID 1591965Notes

Reaction equation

HRID 1591965 reaction equation
COC1C=CC(C[N:8]2[C:12](=[O:13])[CH2:11][N:10]([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[S:9]2(=[O:22])=[O:21])=CC=1.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]>C([SiH](CC)CC)C.O>[OH:31][C:25]([C:27]([F:30])([F:29])[F:28])=[O:26].[O:22]=[S:9]1(=[O:21])[N:10]([CH2:14][C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[CH2:11][C:12](=[O:13])[NH:8]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67139716HCID 67139716, compound

Product 1

HCID 86591035HCID 86591035, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12052TriethylsilaneSolvent

Conditions

Temperature
80 °C

Procedure

The title C compound, 2-(4-methoxybenzyl)-1,1-dioxo-5-pyridin-4-ylmethyl-1,2,5-thiadiazolidin-3-one (73 mg, 0.21 mmol) in a mixture of TFA (4.75 mL) and triethylsilane (0.25 mL) in a 20 mL scintillation vial with polyseal cap is heated in an 80° C. oil bath for 16 h. The reaction solvents are removed by overnight evaporation on a Savant SpeedVac system. This gives a white solid which is dissolved in water, filtered through a 0.45 micron PTFE filter disc, and water is removed by lyophilization to give 1,1-dioxo-5-pyridin-4-ylmethyl-1,2,5-thiadiazolidin-3-one TFA salt as an amorphous white solid: [M+1]+=228.

Workup

  1. customcap
  2. customThe reaction solvents are removed by overnight
  3. customevaporation on a Savant SpeedVac system
  4. customThis gives a white solid which
  5. filtrationfiltered through a 0.45 micron PTFE
  6. filtrationfilter disc, and water
  7. customis removed by lyophilization

Sources & evidence

ORD record
ord-85cf4eca1f064dc185598f15349bc5e9
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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