HCID 86606235, compound → HCID 11178085, compound

HRID 1864530Notes

Reaction equation

HRID 1864530 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[C:17]([CH2:20][N:21]([CH3:30])[C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[S:18][CH:19]=3)=[CH:11][CH:10]=2)[S:3]1>O1CCOCC1.[Pd]>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:16]=[C:17]([CH2:20][N:21]([CH3:30])[C:22](=[O:29])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[S:18][CH:19]=3)=[CH:13][CH:14]=2)[S:3]1

Participants

4

Reactant 1

HCID 86606235HCID 86606235, compound

Product 1

HCID 11178085HCID 11178085, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

2 g (1 mass equivalent) of palladium-on-charcoal are added to a solution of 2 g (4.6 mmol) of N-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)phenyl]thiophen-2-ylmethyl}-N-methylbenzamide in 20 ml of dioxane that has been degassed beforehand, and the reaction medium is placed under 3 atm of hydrogen, at 50° C. for 6 hours. After filtering off the palladium through Celite, the filtrate is concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 9.5/0.5 dichloromethane/methanol mixture. 1.5 g (75%) of N-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenyl]thiophen-2-ylmethyl}N-methylbenzamide are obtained in the form of a solid with a melting point of 134° C.

Workup

  1. customhas been degassed beforehand
  2. filtrationAfter filtering off the palladium through Celite
  3. concentrationthe filtrate is concentrated under vacuum
  4. customThe residue obtained
  5. customis purified by chromatography on a column of silica
  6. washeluted with a 9.5/0.5 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-6a93e086d5a44bfa9d52bc3bc0559946
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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