4-(6-Methoxy-[1,5]naphthyridin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester → Piperidine-4-carboxylic acid (6-methoxy-[1,5]naphthyridin-4-yl)-amide

HRID 456582

Reaction equation

HRID 456582 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:31])[NH:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([O:29][CH3:30])[N:27]=3)[N:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.C(OCC)(=O)C.[Pd].C>[CH3:30][O:29][C:26]1[N:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][CH:20]=[C:19]2[NH:18][C:17]([CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[O:31]

Participants

4

Reactant 1

HCID 112471584-(6-Methoxy-[1,5]naphthyridin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 11231497Piperidine-4-carboxylic acid (6-methoxy-[1,5]naphthyridin-4-yl)-amideYield 59%

Reagents, catalysts & solvents 2

HCID 14818447PalladiumcarbonCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of (e) (6.0 g, 14.3 mmol) in ethanol/ethyl acetate (150 ml/150 ml) was hydrogenated over 10% Pd/charcoal (5 g) for 1.5 hours. Filtration, washing with ethanol (400 ml) and evaporation of the filtrate gave a white solid (2.4 g, 59%).

Workup

  1. filtrationFiltration
  2. washwashing with ethanol (400 ml) and evaporation of the filtrate

Sources & evidence

ORD record
ord-62de4b780e9d4801979ff0c701b6f06c
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Linked notes

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