5-Hydantoinpropionic acid → 3-(2,5-Dioxo-4-imidazolidinyl)-n-{4-[(2-methyl-4-quinolinyl)methoxy]phenyl}propanamide

HRID 2181067Notes

Reaction equation

HRID 2181067 reaction equation
[NH:1]1[CH:7]([CH2:8][CH2:9][C:10]([OH:12])=O)[C:5](=[O:6])[NH:4][C:2]1=[O:3].Cl.Cl.[CH3:15][C:16]1[CH:25]=[C:24]([CH2:26][O:27][C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.N1CC(=O)NC1=O>>[O:3]=[C:2]1[NH:1][CH:7]([CH2:8][CH2:9][C:10]([NH:32][C:31]2[CH:30]=[CH:29][C:28]([O:27][CH2:26][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=[C:16]([CH3:15])[CH:25]=3)=[CH:34][CH:33]=2)=[O:12])[C:5](=[O:6])[NH:4]1

Participants

4

Reactant 3

HCID 7825-Hydantoinpropionic acidHCID 10006HydantoinHCID 673055374-[(2-Methyl-4-quinolinyl)methoxy]benzenamine dihydrochloride

Product 1

HCID 101367863-(2,5-Dioxo-4-imidazolidinyl)-n-{4-[(2-methyl-4-quinolinyl)methoxy]phenyl}propanamideYield 47.8%

Procedure

(+/−)-5-hydantoinpropionic acid (Dakin; Am. Chem. J. 1910, 44, 49) (50 mg, 0.29 mmol) was coupled with 4-[(2-methyl-4-quinolinyl)methoxy]-aniline bis-HCl salt (213 mg, 0.63 mmol) using general coupling method A to give 58 mg (44%) of the product hydantoin. MS found: (M+H)+=419.

Sources & evidence

ORD record
ord-b133d73d633e42c8891fffba4597d8ac
Source dataset
uspto-grants-2005_05
Patent number
US06890915B2

Reaction notes

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