HCID 44540473, compound → HCID 44541111, compound

HRID 402565Notes

Reaction equation

HRID 402565 reaction equation
C([O:8][NH:9][C:10]([C:12]1[C:17]([O:18]CC2C=CC=CC=2)=[C:16]([CH2:26][O:27][CH3:28])[C:15]([C:29]([N:31]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[CH3:32])=[O:30])=[CH:14][N:13]=1)=[O:11])C1C=CC=CC=1>CO.[Pd]>[F:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][N:31]([CH3:32])[C:29]([C:15]2[C:16]([CH2:26][O:27][CH3:28])=[C:17]([OH:18])[C:12]([C:10]([NH:9][OH:8])=[O:11])=[N:13][CH:14]=2)=[O:30])=[CH:39][CH:38]=1

Participants

4

Reactant 1

HCID 44540473HCID 44540473, compound

Product 1

HCID 44541111HCID 44541111, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 12g (0.100 g, 0.184 mmol, 1 eq) and 10% Pd/C (5 mg) catalyst were stirred in methanol (4.0 mL) under a hydrogen atmosphere for 1 hour. The catalyst was filtered and the reaction mixture was concentrated under vacuum yielding 0.040 g of N5-(4-fluorobenzyl)-N2,3-dihydroxy-4-(methoxymethyl)-N5-methylpyridine-2,5-dicarboxamide (60% yield) as a white solid; MS-ESI m/z 364 [MH]+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-80d577e3fd8a49f482ba7b3f76ad99cc
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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