HCID 58424979, compound → HCID 58424852, compound

HRID 2409439Notes

Reaction equation

HRID 2409439 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10](=[O:17])[N:9]([CH2:18][O:19][CH3:20])[C:8]=2[CH:21]=1)[CH3:3]>C(O)C.ClCCl.[Pd]>[OH:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]2[C:16]3[NH:15][CH2:14][CH2:13][CH2:12][C:11]=3[C:10](=[O:17])[N:9]([CH2:18][O:19][CH3:20])[C:8]=2[CH:21]=1)[CH3:3]

Participants

5

Reactant 1

HCID 58424979HCID 58424979, compound

Product 1

HCID 58424852HCID 58424852, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (650 mg, 2.29 mmol) prepared in step 4 was dissolved in ethanol (10 ml)/dichloromethane (10 ml) and added with 10%-palladium (Pd) (200 mg) at room temperature. The resulting mixture was stirred for one day under hydrogen gas and 10%-palladium was removed by using celite-filter. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography (chloroform:methanol=30:1) to obtain the title compound (320 mg, yield: 49%, white solid).

Workup

  1. custom10%-palladium was removed
  2. filtrationby using celite-filter
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-71bd94fc6c844c50aa0b9594d20cc464
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

Loading…