HCID 86595986, compound → HCID 22061559, compound

HRID 2099705Notes

Reaction equation

HRID 2099705 reaction equation
C(OC(=O)[NH:10][CH2:11][CH:12]1[O:16][C:15]2[CH:17]=[CH:18][C:19]([CH2:21][CH:22]([N:24]([CH3:31])[C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH3:23])=[CH:20][C:14]=2[O:13]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:10][CH2:11][CH:12]1[O:16][C:15]2[CH:17]=[CH:18][C:19]([CH2:21][CH:22]([N:24]([CH3:31])[C:25](=[O:30])[C:26]([F:28])([F:27])[F:29])[CH3:23])=[CH:20][C:14]=2[O:13]1

Participants

5

Reactant 2

HCID 86595986HCID 86595986, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22061559HCID 22061559, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 150 mg (0.33 mmol) of 1I in 10 ml of methanol was added 24 mg of 10% Pd—C, and the mixture was hydrogenated for 4 hours at room temperature under atmospheric pressure using a hydrogen filled balloon. The reaction mixture was filtered through CELITE and the residue was washed with 20 mL of methanol. The filtrates were combined and concentrated to dryness under reduced pressure. The residue was purified by silica gel flash column chromatography using 10% methanol in ethyl acetate to give 95 mg (0.29 mmol, 86%) of 1J as a colorless oil (M+H, 319).

Workup

  1. filtrationThe reaction mixture was filtered through CELITE
  2. washthe residue was washed with 20 mL of methanol
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-b2397f8dc3444bc893c6585e8f881f0b
Source dataset
uspto-grants-2009_08
Patent number
US07569676B2

Reaction notes

Loading…