HCID 86605709, compound → HCID 23076444, compound

HRID 2221537Notes

Reaction equation

HRID 2221537 reaction equation
[CH2:1]([O:8][C:9]1[C:13](/[CH:14]=[C:15]2/[C:16](=[O:22])[N:17]([CH3:21])[C:18](=[O:20])[S:19]/2)=[CH:12][N:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].O1CCCC1>[CH2:1]([O:8][C:9]1[C:13]([CH2:14][CH:15]2[S:19][C:18](=[O:20])[N:17]([CH3:21])[C:16]2=[O:22])=[CH:12][N:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86605709HCID 86605709, compound

Product 1

HCID 23076444HCID 23076444, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(5Z)-5-[(3-Benzyloxy-1-phenyl-1H-pyrazol-4-yl)methylene]-3-methyl-1,3-thiazolidine-2,4-dione (1.0 g), 5% palladium on carbon (1.0 g) and tetrahydrofuran (150 mL) were subjected to catalytic reduction under a hydrogen atmosphere and 4.8 kgf/cm2 pressure. The catalyst was filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:6, v/v) to give 5-[(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methyl]-3-methyl-1,3-thiazolidine-2,4-dione as colorless crystals (0.56 g, yield 55%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 115-116° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. washeluted with ethyl acetate-hexane (1:6, v/v)

Sources & evidence

ORD record
ord-428472263cc44eaa9d67c96473e5725a
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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