N5-(1,3-benzodioxol-5-ylmethyl)-N2,3-dibenzyloxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamide → N5-(benzo[d][1,3]dioxol-5-ylmethyl)-N2,3-dihydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamide

HRID 402560Notes

Reaction equation

HRID 402560 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[C:15]([CH2:39][OH:40])=[C:16]([O:31]CC4C=CC=CC=4)[C:17]([C:20]([NH:22][O:23]CC4C=CC=CC=4)=[O:21])=[N:18][CH:19]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1>CO.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[C:15]([CH2:39][OH:40])=[C:16]([OH:31])[C:17]([C:20]([NH:22][OH:23])=[O:21])=[N:18][CH:19]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 1

HCID 71589574N5-(1,3-benzodioxol-5-ylmethyl)-N2,3-dibenzyloxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamide

Product 1

HCID 44541023N5-(benzo[d][1,3]dioxol-5-ylmethyl)-N2,3-dihydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The final product of Example 3 above (0.170 g, 0.330 mmol, 1 eq) and 10% Pd/C (5 mg) catalyst were mixed in methanol (4.0 mL) under an atmosphere of hydrogen 1 hour. The catalyst was filtered and reaction mixture was concentrated under vacuum yielding 0.029 g of N5-(benzo[d][1,3]dioxol-5-ylmethyl)-N2,3-dihydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamide (90% yield) as a white solid; 1H-NMR (400 MHz, MeOD): δ=8.176 (s, 1H), 6.93 (m, 3H), 5.95 (s, 2H), 4.77 (s, 2H), 4.50 (s, 2H); MS-ESI m/z 362 [MH]+.

Workup

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

Sources & evidence

ORD record
ord-328c033da351429b8b9cf18072b62dbc
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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