3-(benzyloxy)-N-cyclobutyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide → N-cyclobutyl-3-hydroxy-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide

HRID 2218111Notes

Reaction equation

HRID 2218111 reaction equation
[CH:1]1([NH:5][C:6]([C:8]2[N:9]([CH3:24])[C:10]([CH3:23])=[CH:11][C:12](=[O:22])[C:13]=2[O:14]CC2C=CC=CC=2)=[O:7])[CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[CH:1]1([NH:5][C:6]([C:8]2[N:9]([CH3:24])[C:10]([CH3:23])=[CH:11][C:12](=[O:22])[C:13]=2[OH:14])=[O:7])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 666589483-(benzyloxy)-N-cyclobutyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide

Product 1

HCID 59769606N-cyclobutyl-3-hydroxy-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamideYield 51.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-cyclobutyl-3-benzyloxy-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide (1.528 g, 4.68 mmol, 1.0 equiv), 10% Pd on activated carbon (200 mg, wet), and ethanol (200 ml) was stirred under 50 psi of H2 at room temperature for 2.5 h. The catalyst was filtered through Celite and the filtrate was evaporated to give a solid, which was recrystallized from MeOH gave the titled compound (0.57 g, 51.5%) as a white solid.

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. customthe filtrate was evaporated
  3. customto give a solid, which
  4. customwas recrystallized from MeOH

Sources & evidence

ORD record
ord-32fc1d7d080348a3a09afd8e6886e729
Source dataset
uspto-grants-2008_08
Patent number
US07410985B2

Reaction notes

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