HCID 178488858, compound → HCID 178488857, compound

HRID 571039Notes

Reaction equation

HRID 571039 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([C:16]2[CH:32]=[CH:31][C:19]3[NH:20][C:21]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)=[N:22][C:18]=3[CH:17]=2)[CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([C:16]2[CH:32]=[CH:31][C:19]3[NH:20][C:21]([C:23]4[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=4)=[N:22][C:18]=3[CH:17]=2)[CH:10]=1

Participants

4

Reactant 1

HCID 178488858HCID 178488858, compound

Product 1

HCID 178488857HCID 178488857, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

3-(Benzyloxy)-1-[2-(4-methoxyphenyl)-1H-benzimidazol-5-yl]pyridin-4(1H)-one (912 mg, 10 mmol) and 10% Pd/C (100 mg) in EtOH (300 mL) was stirred under an H2 balloon for 3 hours. After this time, LCMS indicated that the reaction was complete. After evacuation and purge with N2 (3×), the EtOH solution was heated at 60° C. for 1 h, filtered, and the catalyst was washed with EtOH (4×50 mL). The combined EtOH solution was concentrated to provide the desired product 3-hydroxy-1-[2-(4-methoxyphenyl)-1H-benzimidazol-5-yl]pyridin-4(1H)-one as a slightly yellow solid. 1H NMR (500 MHz, DMSO): δ 13.05 (s, broad, 1 H); 8.15 (d, J=8.3 Hz, 2 H); 7.89 (d, J=6.9 Hz, 1 H); 7.71 (m, 3 H); 7.34 (d, J=7.9 Hz, 1 H); 7.13 (d, J=8.6 Hz, 2 H); 6.32 (d, J=7.3 Hz, 1 H); 3.85 (s, 3 H); LCMS (M+H)+ 334; HRMS Calcd for (C19H15N3O3+H)+ 334.1186. Found 334.1188.

Workup

  1. customAfter evacuation and purge with N2 (3×)
  2. filtrationfiltered
  3. washthe catalyst was washed with EtOH (4×50 mL)
  4. concentrationThe combined EtOH solution was concentrated

Sources & evidence

ORD record
ord-df8f3ab5bff443778d8376473494a3c9
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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