6-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide → N-(4-tert-Butylbenzyl)-6-hydroxy-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 1961478Notes

Reaction equation

HRID 1961478 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[N:17][CH:18]=1)[N:15]=[C:14]([CH3:19])[C:13]([C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=1)=[O:21])=[CH:12]2)C1C=CC=CC=1>CO.[Pd]>[C:30]([C:27]1[CH:26]=[CH:25][C:24]([CH2:23][NH:22][C:20]([C:13]2[C:14]([CH3:19])=[N:15][C:16]3[C:11]([CH:12]=2)=[CH:10][C:9]([OH:8])=[CH:18][N:17]=3)=[O:21])=[CH:29][CH:28]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

4

Reactant 1

HCID 667454906-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide

Product 1

HCID 66745406N-(4-tert-Butylbenzyl)-6-hydroxy-2-methyl-1,8-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-(Benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide (62.0 mg, 0.14 mmol) was dissolved in MeOH (2 ml). Pd (C) (3.1 mg) was added to the solution. The mixture was hydrogenated at atmospheric pressure for 24 h. Then it was filtered through a pad of celite and concentrated under reduced pressure. The residue was washed with CH2Cl2 yielding 37 mg (76%) of the title compound.

Workup

  1. filtrationThen it was filtered through a pad of celite
  2. concentrationconcentrated under reduced pressure
  3. washThe residue was washed with CH2Cl2 yielding 37 mg (76%) of the title compound

Sources & evidence

ORD record
ord-cfb91ff860be49cfa1fe0c129da0799e
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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