N-Methylbenzylamine → 5-{5-[(Benzyl methylamino)methyl]furan-2-yl)-3-ethyl-6-methyl-1H-pyridin-2-one

HRID 1921467Notes

Reaction equation

HRID 1921467 reaction equation
[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[O:15][C:14]([CH:16]=O)=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].[CH2:18]([NH:25][CH3:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([N:25]([CH2:16][C:14]1[O:15][C:11]([C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[C:8](=[O:9])[NH:7][C:6]=2[CH3:10])=[CH:12][CH:13]=1)[CH3:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 7669N-MethylbenzylamineHCID 588086555-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)furan-2-carbaldehyde

Product 1

HCID 588085495-{5-[(Benzyl methylamino)methyl]furan-2-yl)-3-ethyl-6-methyl-1H-pyridin-2-oneYield 53%

Procedure

5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl]furan-2-carbaldehyde is reacted with benzyl methylamine as described in Method A, Example 123 to give the title compound as a solid (53% yield). LC/MS: RT 2.08 min; m/e 337 (M+H); 1H NMR (δ, ppm): 11.6 (1H, s), 7.46 (1H, s); 7.3 (5H, m); 6.4 (2H, dd), 3.6 (2H, s), 3.55 (2H, s), 2.4 (2H, m), 2.36 (2H, s), 2.2 (3H, s), 1.05 (3H, t).

Sources & evidence

ORD record
ord-0b762e7e98d449ca9b5da710a07c93de
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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