HCID 58424897, compound → HCID 58424908, compound

HRID 2409449Notes

Reaction equation

HRID 2409449 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:9](=[O:17])[N:8]([CH2:18][O:19][CH3:20])[C:7]=2[CH:6]=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:4]=1>ClCCl.CO.[Pd]>[CH3:1][O:2][C:3]1[C:16]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:17])[N:8]([CH2:18][O:19][CH3:20])[C:7]=2[CH:6]=[C:5]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:4]=1

Participants

5

Reactant 1

HCID 58424897HCID 58424897, compound

Product 1

HCID 58424908HCID 58424908, compoundYield 58.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (776.5 mg, 2.27 mmol) prepared in step 6 was dissolved in dichloromethane and methanol, added with 10%-palladium (Pd) (80.0 mg). The resulting mixture was stirred at room temperature for 20 hours under hydrogen gas. After completion, 10%-palladium (Pd) was removed by celite-filter and the solvent was concentrated under reduced pressure. The residue was then purified by flash column chromatography (dichloromethane:ethyl acetate=3:1) to obtain the title compound (458 mg, yield: 58.2%, white solid).

Workup

  1. customAfter completion, 10%-palladium (Pd) was removed
  2. filtrationby celite-filter
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was then purified by flash column chromatography (dichloromethane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f9ecd185aa3447eba019229a6a60c572
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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