Piperidine → N-(4-tert-butylbenzyl)-6-iodo-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 1961476Notes

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][C:25]([I:28])=[CH:24][C:21]=1[CH:22]=O.N1CCCCC1>CO>[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)=[CH:24][C:25]([I:28])=[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 (104.2 mg, 0.42 mmol) and 2-amino-5-iodonicotinaldehyde (95.0 mg, 0.38 mmol) suspended in piperidine (151.0 μl, 1.53 mmol). The tube was sealed and the mixture heated to 120° C. for 2 h. The mixture was allowed to cool, diluted with MeOH, adsorbed in silica and purified by flash chromatography (CH2Cl2/MeOH 99:1→97:3) yielding 110 mg of the title compound (63%).

Workup

customIn a screw cap pressure tube
customThe tube was sealed
temperatureto cool
custompurified by flash chromatography (CH2Cl2/MeOH 99:1→97:3)

Sources & evidence

ORD record: ord-c289e612dfe24cfab3c2822b6036b7d6
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415333B2

Reaction notes

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