N2,3-bis(benzyloxy)-N5-(3,4-dichlorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide → N5-(3,4-dichlorobenzyl)-N2,3-dihydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamide

HRID 402569Notes

Reaction equation

HRID 402569 reaction equation
C([O:8][NH:9][C:10]([C:12]1[C:17]([O:18]CC2C=CC=CC=2)=[C:16]([CH2:26][OH:27])[C:15]([C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=2)=[O:29])=[CH:14][N:13]=1)=[O:11])C1C=CC=CC=1>CO.[Pd]>[Cl:39][C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][C:35]=1[Cl:38])[CH2:31][NH:30][C:28]([C:15]1[C:16]([CH2:26][OH:27])=[C:17]([OH:18])[C:12]([C:10]([NH:9][OH:8])=[O:11])=[N:13][CH:14]=1)=[O:29]

Participants

4

Reactant 1

HCID 44539697N2,3-bis(benzyloxy)-N5-(3,4-dichlorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide

Product 1

HCID 44541115N5-(3,4-dichlorobenzyl)-N2,3-dihydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamideYield 4.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Product 15 of example 15 (0.03 g, 0.330 mmol,) and 10% Pd/C (25 mg) catalyst were stirred in methanol (4.0 mL) under an atmosphere of hydrogen for 1 hour. The catalyst was filtered and the reaction mixture was concentrated under vacuum to give 0.006 g of N5-(3,4-dichlorobenzyl)-N2,3-dihydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamide as a white solid; 1H-NMR (400 MHz, dmso): δ=13.01 (s, 1H), 12.0 (s, 1H), 9.51 (s 1H), 9.02 (t 1H), 8.11 (s, 1H), 7.60 (d 1H), 7.40 (m, 2H), 4.68 (s, 2H), 4.48 (s, 2H); MS-ESI m/z 386 [MH]+.

Workup

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

Sources & evidence

ORD record
ord-1edc056295b243aabfe2efaf88023a45
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

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