HCID 68682086, compound → 2-Pyridinamine, 5-(1-azetidinyl)-

HRID 645379Notes

Reaction equation

HRID 645379 reaction equation
[N:1]1([C:5]2[CH:6]=[CH:7][C:8]([N+:11]([O-])=O)=[N:9][CH:10]=2)[CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[N:1]1([C:5]2[CH:6]=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 68682086HCID 68682086, compound

Product 1

HCID 552849632-Pyridinamine, 5-(1-azetidinyl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The 5-(azetidin-1-yl)-2-nitropyridine obtained above is taken up in 10 ml of ethanol and hydrogenated in the presence of 65 mg of 10% palladium-on-charcoal at 30° C. under a pressure of 1 bar. The reaction mixture is filtered and the filtrate is diluted with 7N ammoniacal methanol and then concentrated to dryness at 30° C. under reduced pressure. The residue is taken up in dichloromethane, an insoluble material is removed and the residue obtained after evaporation to dryness is chromatographed on a silica cartridge, elution being carried out with a mixture of dichloromethane and 7N ammoniacal methanol (90/10). The fractions comprising the expected product are combined and concentrated to give 185 mg of 5-(azetidin-1-yl)pyridine-2-amine in the form of a red oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. additionthe filtrate is diluted with 7N ammoniacal methanol
  3. concentrationconcentrated to dryness at 30° C. under reduced pressure
  4. customan insoluble material is removed
  5. customthe residue obtained
  6. customafter evaporation to dryness
  7. customis chromatographed on a silica cartridge, elution
  8. additionbeing carried out with a mixture of dichloromethane and 7N ammoniacal methanol (90/10)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9d10d026716a48aa9141f5927bde5baf
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Reaction notes

Loading…