Tetrahydrofuran → HCID 9845971, compound

HRID 1581647Notes

Reaction equation

HRID 1581647 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:28])[CH2:11][C:12]2[CH:17]=[C:16]([CH:18]=[C:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])[CH:15]=[CH:14][C:13]=2[O:26][CH3:27])=[CH:5][CH:4]=1.O1CCCC1>[Pd].C(O)C>[F:30][C:2]([F:1])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:28])[CH2:11][C:12]2[CH:17]=[C:16]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])[CH:15]=[CH:14][C:13]=2[O:26][CH3:27])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86759439HCID 86759439, compound

Product 1

HCID 9845971HCID 9845971, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[4-(Trifluoromethyl)phenyl]-2-[5-((2,4-dioxothiazolidin-5-ylidene)methyl]-2-methoxyphenyl]acetamide (300 mg, 0.687 mmol), 10% palladium on carbon (300 mg) and a mixed solvent of tetrahydrofuran and ethanol (2:1 v/v, 40 mL) were mixed, and hydrogenation was performed at room temperature and at an initial pressure of 392 kPa. After completion of the reaction, catalyst was filtered and the filtrate was concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=2:1 v/v) to obtain 172 mg (57%) of the title compound as colorless powder.

Workup

  1. customwas performed at room temperature
  2. customAfter completion of the reaction, catalyst
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=2:1 v/v)

Sources & evidence

ORD record
ord-503d2ecc9b0d4f349bf0658283157b88
Source dataset
uspto-grants-2004_05
Patent number
US06730687B1

Reaction notes

Loading…