HCID 86656081, compound → HCID 53327294, compound

HRID 1183113Notes

Reaction equation

HRID 1183113 reaction equation
C([O:8][C:9]1[C:10]([C:25]([NH:27][OH:28])=[O:26])=[N:11][CH:12]=[C:13]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:14]=1[CH3:15])C1C=CC=CC=1>CO.[Pd]>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([C:13]2[C:14]([CH3:15])=[C:9]([OH:8])[C:10]([C:25]([NH:27][OH:28])=[O:26])=[N:11][CH:12]=2)=[O:24])=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 86656081HCID 86656081, compound

Product 1

HCID 53327294HCID 53327294, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.090 g of 3-(benzyloxy)-5-(4-fluorobenzoyl)-N-hydroxy-4-methylpicolinamide (9b; 0.237 mmol, 1 eq.) and 5 mg of 10% Pd/C were dissolved in 4.0 mL of methanol and stirred under an atmospheric hydrogen for 1 hr. The catalyst was then filtered and reaction mixture was concentrated under vacuum. The crude product was purified by Biotage reverse phase chromatography yielding 0.015 g of 5-(4-fluorobenzoyl)-N,3-dihydroxy-4-methylpicolinamide (the product step 9b, example 9) (22% yield) and 0.015 g of the corresponding oxime (E)-5-((4-fluorophenyl)(hydroxyimino)methyl)-N,3-dihydroxy-4-methylpicolinamide (10) (22% yield), both as a white solid.

Workup

  1. filtrationThe catalyst was then filtered
  2. customreaction mixture
  3. concentrationwas concentrated under vacuum
  4. customThe crude product was purified by Biotage reverse phase chromatography

Sources & evidence

ORD record
ord-b88c2412ee7f44b0a655c71b60e5a331
Source dataset
uspto-grants-2014_03
Patent number
US08664248B2

Reaction notes

Loading…