HCID 86655923, compound → HCID 71589531, compound

HRID 402564Notes

Reaction equation

HRID 402564 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][CH2:12][C:13]3[C:14]([CH2:38][OH:39])=[C:15]([O:30]CC4C=CC=CC=4)[C:16]([C:19]([NH:21][O:22]CC4C=CC=CC=4)=[O:20])=[N:17][CH:18]=3)=[CH:9][C:4]=2[O:3][CH2:2]1>[Pd].CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][CH2:12][C:13]3[C:14]([CH2:38][OH:39])=[C:15]([OH:30])[C:16]([C:19]([NH:21][OH:22])=[O:20])=[N:17][CH:18]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 1

HCID 86655923HCID 86655923, compound

Product 1

HCID 71589531HCID 71589531, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 11a (0.024 g, 0.039 mmol, 1 eq) and 10% Pd/C catalyst (5 mg) were stirred in 4.0 mL of methanol overnight under an atmosphere of hydrogen. The catalyst was filtered and the reaction mixture was concentrated under vacuum yielding 0.011 g of 5-((benzo[d][1,3]-dioxol-5-ylmethylamino)methyl)-N,3-dihydroxy-4-(hydroxymethyl)picolinamide (69% yield) as a white solid; MS-ESI m/z 348 [MH]+.

Workup

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

Sources & evidence

ORD record
ord-348a30378ad340c79bb252b4eb64f109
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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