HCID 69028482, compound → HCID 17960605, compound

HRID 1866765Notes

Reaction equation

HRID 1866765 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[N+:14]([O-])=O>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[NH2:14]

Participants

4

Reactant 1

HCID 69028482HCID 69028482, compound

Product 1

HCID 17960605HCID 17960605, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of the title compound of Step A (3.37 g, 75% pure) in ethanol (15 mL) was added palladium hydroxide (170 mg, 20 wt % on carbon). The flask was twice evacuated and flushed with nitrogen and then twice evacuated and flushed with hydrogen. The mixture was vigorously stirred under a balloon of hydrogen for 3 hours before being evacuated, exposed to air and filtered through a pad of Celite®. The solution was concentrated and filtered through a pad of silica gel, eluting with 1% then 5% then 10% methanol in dichloromethane, then 5% triethylamine, 10% methanol, 85% dichloromethane. The material eluting in triethylamine/methanol/dichloromethane was concentrated to give the title compound of Step B (1.5 g) as an off white solid.

Workup

  1. customThe flask was twice evacuated
  2. customflushed with nitrogen
  3. customtwice evacuated
  4. customflushed with hydrogen
  5. custombefore being evacuated
  6. filtrationfiltered through a pad of Celite®
  7. concentrationThe solution was concentrated
  8. filtrationfiltered through a pad of silica gel
  9. washeluting with 1%
  10. washThe material eluting in triethylamine/methanol/dichloromethane
  11. concentrationwas concentrated

Sources & evidence

ORD record
ord-2a2af519cfda4c589fbc3353f4c2e90a
Source dataset
uspto-grants-2009_12
Patent number
US07629463B2

Reaction notes

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