5-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl} 1,1-dioxo-1,2,5-thiadiazolidin-3-one → 5-{2-Hydroxy-4-[2-(2H-pyrazol-3-yl)-ethyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660494Notes

Reaction equation

HRID 660494 reaction equation
C([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C:17]2[N:18](COCC3C=CC=CC=3)[N:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]=1[N:31]1[S:35](=[O:37])(=[O:36])[NH:34][C:33](=[O:38])[CH2:32]1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]2[NH:18][N:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]=1[N:31]1[S:35](=[O:37])(=[O:36])[NH:34][C:33](=[O:38])[CH2:32]1

Participants

4

Reactant 1

HCID 689170015-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl} 1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 249701845-{2-Hydroxy-4-[2-(2H-pyrazol-3-yl)-ethyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl} 1,1-dioxo-1,2,5-thiadiazolidin-3-one (240 mg, 0.40 mmol) is dissolved in methanol (5 mL). 10% Pd/C is added periodically (7×50 mg) at intervals over 4 days. The mixture is stirred under an atmosphere of hydrogen at balloon pressure. The catalyst is removed by filtering the mixture through Celite and the filtrate is concentrated. The residue is chromatographed (reverse phase, 0-25% EtOH/water) to afford the title compound as a grey solid: 1H NMR (CD3OD) δ 7.46 (s, 1H), 7.31 (d, J=8.0 Hz, 1H), 6.75 (s, 1H), 6.71 (d, J=8.0 Hz, 1H) 6.10 (s, 1H) 4.29 (s, 2H), 2.89 (m, 4H); (M+1)+=323.

Workup

  1. customThe catalyst is removed
  2. filtrationby filtering the mixture through Celite
  3. concentrationthe filtrate is concentrated
  4. customThe residue is chromatographed (reverse phase, 0-25% EtOH/water)

Sources & evidence

ORD record
ord-25b3ef4150e543e39003306c5dffa8b1
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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