8-(benzyloxy)-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide → 8-hydroxy-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

HRID 1844153Notes

Reaction equation

HRID 1844153 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([C:15]([C:19]([NH:21][C@H:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23][OH:24])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[C:10]2[N:11]([C:15]([C:19]([NH:21][C@H:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23][OH:24])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 867181778-(benzyloxy)-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 867181768-hydroxy-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

350 mg of 10% palladium/carbon were added to a solution of 3.5 g (9.18 mmol) of 8-(benzyloxy)-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide in 250 ml of ethyl acetate, and hydrogen was applied at room temperature and atmospheric pressure. After 3 h, the mixture was filtered off through kieselguhr, the filter cake was washed intensively with ethyl acetate/methanol and the filtrate was evaporated to dryness. Methyl tert-butyl ether was added to the crude product obtained, the product was triturated and the solid was then filtered off and dried at 40° C. under high vacuum. This gave 2.1 g (79% of theory) of 8-hydroxy-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

Workup

  1. customwas applied at room temperature
  2. filtrationthe mixture was filtered off through kieselguhr
  3. washthe filter cake was washed intensively with ethyl acetate/methanol
  4. customthe filtrate was evaporated to dryness
  5. additionMethyl tert-butyl ether was added to the crude product
  6. customobtained
  7. customthe product was triturated
  8. filtrationthe solid was then filtered off
  9. customdried at 40° C. under high vacuum

Sources & evidence

ORD record
ord-3e0c1e322bef452bb786cb27d167476e
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

Loading…