HCID 67418106, compound → HCID 53380285, compound

HRID 571045Notes

Reaction equation

HRID 571045 reaction equation
[NH2:1][C:2]1[N:3]([C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH:4]=[C:5]([O:9]CC2C=CC=CC=2)[C:6](=[O:8])[CH:7]=1>CCO.[Pd]>[NH2:1][C:2]1[N:3]([C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[CH:4]=[C:5]([OH:9])[C:6](=[O:8])[CH:7]=1

Participants

4

Reactant 1

HCID 67418106HCID 67418106, compound

Product 1

HCID 53380285HCID 53380285, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-amino-5-(benzyloxy)-1-(biphenyl-3-yl)pyridin-4(1H)-one (2.65 g, 7.19 mmol) and 10% Pd/C (230 mg) in EtOH (300 mL) was stirred under an H2 balloon for 2 h. After this time, LCMS indicated that the reaction was complete. After evacuation and purge with N2 (3×), the EtOH solution was warmed to 50° C. and stirred 1 h at 50° C. The warmed EtOH solution was filtered and the catalyst was washed with warmed EtOH (4×50 mL). The combined EtOH solution was concentrated to give 2-amino-1-(biphenyl-3-yl)-5-hydroxypyridin-4(1H)-one as slightly yellow solid. 1H NMR (500 MHz, DMSO): δ 7.81 (d, J=7.9 Hz, 1 H); 7.76 (d, J=7.7 Hz, 2 H); 7.71-7.59 (m, 2 H); 7.49 (t, J=7.6 Hz, 2 H); 7.43-7.37 (m, 2 H); 6.91 (s, 1 H); 5.66 (s, 2 H); 5.54 (s, 1 H). HRMS Calcd for (C17H14N2O2+H)+ 279.1128. Found 279.1128.

Workup

  1. customAfter evacuation and purge with N2 (3×)
  2. stirringstirred 1 h at 50° C
  3. filtrationThe warmed EtOH solution was filtered
  4. washthe catalyst was washed with warmed EtOH (4×50 mL)
  5. concentrationThe combined EtOH solution was concentrated

Sources & evidence

ORD record
ord-d644350b74f541c5b6826e92442cd737
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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