Piperidine → N-(4-tert-butylbenzyl)-2,5-dimethyl-1,8-naphthyridine-3-carboxamide

HRID 1961472Notes

Reaction equation

[C:1]([C:5]1[CH:18]=[CH:17][C:8]([CH2:9][NH:10][C:11](=[O:16])[CH2:12][C:13](=O)[CH3:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]1[N:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH:22]=O.N1CCCCC1.CCOC(C)=O>CCO>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([CH2:9][NH:10][C:11]([C:12]2[C:13]([CH3:14])=[N:19][C:20]3[C:21]([CH:22]=2)=[C:24]([CH3:28])[CH:25]=[CH:26][N:27]=3)=[O:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 120 °C

Procedure

In a screw cap pressure tube were N-(4-tert-butylbenzyl)-3-oxobutanamide (94.5 mg, 0.38 mmol), 2-amino-4-methylnicotinaldehyde (52.0 mg, 0.38 mmol) and piperidine (151.0 μl, 1.53 mmol) suspended in EtOH (0.5 ml). The tube was sealed and the mixture heated to 120° C. for 1.5 h. The mixture was allowed to cool. EtOAc was added and the mixture washed with H2O, dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography CH2Cl2/MeOH 96/4 yielding 61.5 mg of the title compound (47%).

Workup

customIn a screw cap pressure tube
customThe tube was sealed
temperatureto cool
washthe mixture washed with H2O
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography CH2Cl2/MeOH 96/4 yielding 61.5 mg of the title compound (47%)

Sources & evidence

ORD record: ord-6b9578044c0f45c8889ce1379e8dafb6
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415333B2

Reaction notes

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