N-Benzyl-2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide → N-Benzyl-2-(3-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

HRID 1887309Notes

Reaction equation

HRID 1887309 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22]CC3C=CC=CC=3)[C:17]2=[O:30])=[N:13][C:12]=1[CH3:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:17]2=[O:30])=[N:13][C:12]=1[CH3:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 24985273N-Benzyl-2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 24985274N-Benzyl-2-(3-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamideYield 24.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-benzyl-2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide (0.14 g, 0.32 mmol) and 20 wt. % palladium on activated carbon (0.10 g) in methanol (50 mL) was stirred under an atmosphere of hydrogen for 2 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography followed by recrystallization from methanol (10 mL) to afford the title compound (0.027 g, 8%): mp 225-228° C.; 1H NMR (300 MHz, CD3OD) δ 8.63 (d, J=7.6 Hz, 1H), 7.42-7.26 (m, 5H), 6.20-6.10 (m, 1H), 5.87-5.83 (m, 1H), 4.36 (d, J=6.0 Hz, 2H), 2.58 (s, 3H); MS (ES+) m/z 342.2 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography
  4. customfollowed by recrystallization from methanol (10 mL)

Sources & evidence

ORD record
ord-56e9e06d87cc43fd926b2ec9539a8c04
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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