benzyl 4-[(1R,2S)-2-(2-{[3-methyl-5-(2-oxoimidazolidin-1-yl)pyridin-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carboxylate → 1-(5-methyl-6-{2-[(1S,2R)-2-piperidin-4-ylcyclopropyl]ethoxy}pyridine-3-yl)imidazolidin-2-one

HRID 1850741Notes

Reaction equation

HRID 1850741 reaction equation
[CH3:1][C:2]1[C:3]([O:14][CH2:15][CH2:16][C@@H:17]2[CH2:19][C@@H:18]2[CH:20]2[CH2:25][CH2:24][N:23](C(OCC3C=CC=CC=3)=O)[CH2:22][CH2:21]2)=[N:4][CH:5]=[C:6]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH:7]=1.[H][H]>CCO.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH:5]=[N:4][C:3]=1[O:14][CH2:15][CH2:16][C@@H:17]1[CH2:19][C@@H:18]1[CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 70856309benzyl 4-[(1R,2S)-2-(2-{[3-methyl-5-(2-oxoimidazolidin-1-yl)pyridin-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 867111881-(5-methyl-6-{2-[(1S,2R)-2-piperidin-4-ylcyclopropyl]ethoxy}pyridine-3-yl)imidazolidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 4-[(1R,2S)-2-(2-{[3-methyl-5-(2-oxoimidazolidin-1-yl)pyridin-2-yl]oxy}ethyl)cyclopropyl]piperidine-1-carboxylate (18 mg, 0.041 mmol) in 1 mL of EtOH was treated with 10% palladium on carbon (10 mg) for 2.5 hrs under 1 atm. of hydrogen gas. The catalyst was filtered off via Gilsen 0.045 μM PTFE syringe filter and the filtrate was concentrated in vacuo to give the product used for the next reaction without further purification. LCMS (ESI) m/z 345 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered off via Gilsen 0.045 μM PTFE syringe
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give the product
  5. customused for the next reaction without further purification

Sources & evidence

ORD record
ord-49871a17f30b404da0ff77ea6752191f
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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