HCID 70106277, compound → HCID 19595252, compound

HRID 612468Notes

Reaction equation

HRID 612468 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([NH:14][CH:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH2:16]1)[CH2:7]2>[Pd].C(O)C>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][CH:2]=[C:3]2[C:8]=1[CH2:7][N:6]([NH:14][C:15]1[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=1)[CH2:5][CH2:4]2

Participants

4

Reactant 1

HCID 70106277HCID 70106277, compound

Product 1

HCID 19595252HCID 19595252, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-bromo-3,4-dihydro-8-methoxy-1H-isoquinolin-2-yl-4-pyridinylamine (0.8 g), ethanol (75 ml) and 5% palladium-on-carbon (0.1 g) was hydrogenated at 55 psi overnight in a Parr shaker at ambient temperature. The reaction mixture was filtered through a pad of celite, the pad was washed with methanol, and the filtrate was concentrated. Aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was chromatographed on silica gel on a Chromatotron, eluting with 1% triethylamine/5% methanol/94% ethyl acetate. The appropriate fractions were collected and concentrated. The residue was crystallized in hot ethyl acetate to give 0.25 g (41%) of product, mp 170-171° C.

Workup

  1. customwas hydrogenated at 55 psi overnight in a Parr shaker at ambient temperature
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washthe pad was washed with methanol
  4. concentrationthe filtrate was concentrated
  5. additionAqueous sodium hydrogen carbonate was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customThe residue was chromatographed on silica gel on a Chromatotron
  11. washeluting with 1% triethylamine/5% methanol/94% ethyl acetate
  12. customThe appropriate fractions were collected
  13. concentrationconcentrated
  14. customThe residue was crystallized in hot ethyl acetate

Sources & evidence

ORD record
ord-a0d0935518c7446abe0e3d88097f1e41
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

Loading…