HCID 44434060, compound → HCID 59730173, compound

HRID 228485Notes

Reaction equation

HRID 228485 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=3)[CH:14]=2)[CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].CCO>[CH2:9]1[C:10]2[C:15](=[CH:14][C:13]([O:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=3)=[CH:12][CH:11]=2)[CH2:16][NH:8]1

Participants

5

Reactant 2

HCID 44434060HCID 44434060, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59730173HCID 59730173, compoundYield 11.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine 6-(2-Benzyl-2,3-dihydro-1H-isoindol-5-yloxy)-nicotinamide (230.0 mg, 0.67 mmol), EtOH (5 mL), 10% Pd—C (45.0 mg), and a Hydrogen balloon. Stir the reaction at room temperature for 168 hours at atmospheric pressure. Filter the reaction mixture through a pad of Celite using MeOH eluent and then concentrate the filtrate under reduced pressure. Add the mixture to a 2 g SCX column, wash with MeOH, and elute using 1N NH3-MeOH. After concentrating under reduced pressure, purify the mixture by flash chromatography using 10% 1N NH3-MeOH/DCM eluent to afford 19.2 mg, 0.08 mmol (11% yield) of the title compound as a white solid: 1H NMR (500 MHz, d-Methanol); 4.1-4.3 (4H, br m), 6.9-7.1 (3H, m), 7.3-7.4 (1H, m), 8.2-8.3 (1H, m), 8.6 (1H, s); MS m/z 254 (M).

Workup

  1. customthe reaction at room temperature for 168 hours at atmospheric pressure
  2. filtrationFilter the reaction mixture through a pad of Celite
  3. concentrationconcentrate the filtrate under reduced pressure
  4. additionAdd the mixture to a 2 g SCX column
  5. washwash with MeOH
  6. washelute
  7. concentrationAfter concentrating under reduced pressure
  8. custompurify the mixture by flash chromatography

Sources & evidence

ORD record
ord-884c93b1e8384b97ab4ce132a95b5643
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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