HCID 24985947, compound → HCID 54742342, compound

HRID 1887329Notes

Reaction equation

HRID 1887329 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[S:16][C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:18]([CH3:20])[N:19]=2)[C:11](=[O:26])[CH:10]=1)C1C=CC=CC=1>[Pd].O1CCCC1>[OH:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[S:16][C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:18]([CH3:20])[N:19]=2)[C:11](=[O:26])[CH:10]=1

Participants

4

Reactant 1

HCID 24985947HCID 24985947, compound

Product 1

HCID 54742342HCID 54742342, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylate (7.00 g, 18.0 mmol) and 20 wt. % palladium on activated carbon (3 g) in anhydrous tetrahydrofuran (300 mL) was stirred under an atmosphere of hydrogen for 2 hours. The mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was recrystallized from ethyl acetate to afford the title compound as a colorless solid (4.00 g, 80%): mp 270-273° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.58 (d, J=8.0 Hz, 1H), 6.27 (dd, J=8.0, 2.5 Hz, 1H), 5.81 (d, J=2.5 Hz, 1H), 4.24 (q, J=7.1 Hz, 2H), 2.58 (s, 3H), 1.26 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, DMSO-d6) δ 168.0, 162.5, 161.7, 156.5, 155.3, 132.4, 119.0, 104.7, 97.9, 61.2, 17.6, 14.6; MS (ES+) m/z 281.0 (M+1).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-32ff2bea47b44e978532a6e5af57890e
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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