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 420477Notes

Reaction equation

HRID 420477 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. M.p. 277.3° C. (dec); 1H-NMR (DMSO-d6, 400 MHz) δ 1.68-1.70 (m, 2H, cyclobutyl H), 1.95-2.01 (m, 2H, cyclobutyl H), 2.20-2.26 (m, 2H, cyclobutyl H), 2.29 (s, 3H, CH3), 3.41 (s, 3H, NCH3), 4.31-4.35 (m, 1H, CH), 6.13 (s, 1H, CH), 8.98 (br, 1H, NH); MS (m/z) 237 (M++1), 185, 166, 123.

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-6196231e279f4741b266e41b0fb1d60c
Source dataset
uspto-grants-2012_01
Patent number
US08097624B2

Reaction notes

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