Piperidine → N-(4-tert-butylbenzyl)-2,7-dimethyl-1,8-naphthyridine-3-carboxamide

HRID 1961471Notes

Reaction equation

HRID 1961471 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([C:15]1[CH:28]=[CH:27][C:18]([CH2:19][NH:20][C:21](=[O:26])[CH2:22][C:23](=O)[CH3:24])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].N1CCCCC1>CCO>[C:11]([C:15]1[CH:28]=[CH:27][C:18]([CH2:19][NH:20][C:21]([C:22]2[C:23]([CH3:24])=[N:1][C:2]3[C:3]([CH:4]=2)=[CH:6][CH:7]=[C:8]([CH3:10])[N:9]=3)=[O:26])=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 534010302-Amino-6-methylnicotinaldehydeHCID 86661979N-(4-tert-butylbenzyl)-3-oxobutanamide

Product 1

HCID 66633995N-(4-tert-butylbenzyl)-2,7-dimethyl-1,8-naphthyridine-3-carboxamideYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 200 mg (1.47 mmol) 2-amino-6-methylnicotinaldehyde, 400 mg (1.62 mmol) N-(4-tert-butylbenzyl)-3-oxobutanamide and 15 (0.15 mmol) piperidine in 3 ml EtOH was refluxed for 36 h. The reaction mixture was concentrated under reduced pressure. Flash chromatography (CH2Cl2/MeOH 20:1) afforded 258 mg (51%) of the title compound as a yellow-brown amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f90a1ccde2e940e5bd13b52d3332c612
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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