HCID 44553783, compound → HCID 54746065, compound

HRID 714396Notes

Reaction equation

HRID 714396 reaction equation
[CH2:1]([NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC=CC=3)=[CH:18][C:17]2=[O:30])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[CH2:1]([NH:8][C:9]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]2=[O:30])[CH:11]=1)=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 44553783HCID 44553783, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54746065HCID 54746065, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-benzyl-2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)isonicotinamide (0.88 g, 2.14 mmol) and 20 weight % palladium on activated carbon (0.10 g) in methanol (50 mL) was stirred in atmospheric pressure of hydrogen for 2 hours. The resulting solution was filtered and concentrated in vacuo. The residue was recrystallized from methanol (10 mL) to give 4-hydroxy-2-oxo-2H-[1,2′]bipyridinyl-4′-carboxylic acid benzylamide as a colorless solid (0.34 g, 50%): mp 102-105° C. (methanol); 1H NMR (300 MHz, CD3OD) δ 8.66 (d, J=5.1 Hz, 1H), 8.05 (s, 1H), 7.81-7.78 (m, 2H), 7.36-7.24 (m, 5H), 6.20-6.17 (m, 1H), 5.86 (s, 1H) 4.57 (s, 2H); 13C NMR (75 MHz, CD3OD) δ 167.6, 164.0, 162.9, 150.8, 147.9, 142.4, 136.5, 135.9, 126.6, 125.7, 125.4, 119.5, 117.9, 100.9, 96.8, 41.8; MS (ES+) m/z 322.3 (M+1).

Workup

  1. filtrationThe resulting solution was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was recrystallized from methanol (10 mL)

Sources & evidence

ORD record
ord-8452d365134a49fba0b54954406cc33e
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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