HCID 68839776, compound → 5-(2-Hydroxy-4-thiazol-5-yl-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660727Notes

Reaction equation

HRID 660727 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([C:15]2[S:19][CH:18]=[N:17][CH:16]=2)[CH:12]=[CH:11][C:10]=1[N:20]1[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]1)C1C=CC=CC=1>CCO.O.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([C:15]2[S:19][CH:18]=[N:17][CH:16]=2)[CH:12]=[CH:11][C:10]=1[N:20]1[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]1

Participants

5

Reactant 1

HCID 68839776HCID 68839776, compound

Product 1

HCID 577774635-(2-Hydroxy-4-thiazol-5-yl-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(2-benzyloxy-4-thiazol-5-yl-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (87 mg, 0.217 mmol) in EtOH (2.5 mL) and water (22.5 mL) is added 10% Pd/C (100 mg) and the mixture is stirred under an atmosphere of H2 for 2.5 h. The mixture is filtered through Celite and the filtrate evaporated. The residue is purified by reverse phase HPLC (CH3CN/water/0.1% TFA) to afford the title compound as a light yellow solid: 1H NMR (CD3O4.37 (s, 1H), 7.04 (d, J=8 Hz, 1H), 7.08 (s, 1H), 7.35 (d, J=8 Hz, 1H), 7.97 (s, 1H), 8.79 (s, 1H); (M−1)−=310.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. customthe filtrate evaporated
  3. customThe residue is purified by reverse phase HPLC (CH3CN/water/0.1% TFA)

Sources & evidence

ORD record
ord-3772a018c3a34d4dbbb13f0effa17b01
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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