Methanol → HCID 44541113, compound

HRID 402563Notes

Reaction equation

HRID 402563 reaction equation
C([O:8][NH:9][C:10](=[O:37])[C:11]1[C:16]([O:17]CC2C=CC=CC=2)=[C:15]([CH2:25][OH:26])[C:14]([CH2:27][NH:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[CH:13][N:12]=1)C1C=CC=CC=1.[CH3:38]O>[Pd]>[F:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][NH:28][CH2:27][C:14]2[C:15]([CH2:25][O:26][CH3:38])=[C:16]([OH:17])[C:11]([C:10]([NH:9][OH:8])=[O:37])=[N:12][CH:13]=2)=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 44540376HCID 44540376, compound

Product 1

HCID 44541113HCID 44541113, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Compound 9a (0.013 g, 0.019 mmol, 1 eq) and 10% Pd/C catalyst (5 mg) were stirred in 4 mL of methanol under an atmosphere of hydrogen for 12 hrs. The catalyst was filtered and reaction mixture was concentrated under vacuum yielding 0.006 g of 5-((4-fluorobenzylamino)methyl)-N,3-dihydroxy-4-(methoxymethyl)picolinamide) (75% yield) as a white solid; MS-ESI m/z 322 [MH]+.

Workup

  1. filtrationThe catalyst was filtered
  2. customreaction mixture
  3. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-a0a8eeaff03247bdb92f17bf7e611ac6
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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