HCID 71136196, compound → HCID 71117262, compound

HRID 629888Notes

Reaction equation

HRID 629888 reaction equation
[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16][CH2:15][CH:14]=3)=[CH:10][CH:11]=2)[N:6]([CH3:26])[C:5]1=[O:27].[H][H]>[Pd].CCO>[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([CH:13]3[CH2:14][CH2:15][CH2:16][N:17]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:18]3)=[CH:10][CH:11]=2)[N:6]([CH3:26])[C:5]1=[O:27]

Participants

5

Reactant 2

HCID 71136196HCID 71136196, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71117262HCID 71117262, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a round bottom flask containing tert-butyl 5-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-3,6-dihydropyridine-1(2H)-carboxylate (17-27) (1 g, 2.497 mmol), was added EtOH (25 mL) & Palladium on Carbon (10% by weight on carbon) (0.25 g, 0.2349 mmol). A balloon containing hydrogen gas was then attached and purged 3× with vacuum/hydrogen. The reaction mixture was permitted to stir at room temperature for 1 hour, then purged 3× with vacuum/nitrogen, diluted with EtOH, filtered & concentrated to yield tert-butyl 3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]piperidine-1-carboxylate (18-1). LRMS (M+H)+: observed=403.3, calculated=403.5.

Workup

  1. custompurged 3× with vacuum/hydrogen
  2. custompurged 3× with vacuum/nitrogen
  3. additiondiluted with EtOH
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3f4b19255ab04009b457f642f91ba0e2
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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