Hydantoin → 2-(4-Methyl-2,5-dioxo-4-imidazolidinyl)-n-{4-[(2-methyl-4-quinolinyl)methoxy]phenyl}acetamide

HRID 1455289Notes

Reaction equation

HRID 1455289 reaction equation
[CH3:1][C:2]1([CH2:9][C:10]([OH:12])=O)[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].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>>[CH3:1][C:2]1([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:3](=[O:8])[NH:4][C:5](=[O:7])[NH:6]1

Participants

4

Reactant 3

HCID 10006HydantoinHCID 2903362-(4-Methyl-2,5-dioxoimidazolidin-4-yl)acetic acidHCID 673055374-[(2-Methyl-4-quinolinyl)methoxy]benzenamine dihydrochloride

Product 1

HCID 102021482-(4-Methyl-2,5-dioxo-4-imidazolidinyl)-n-{4-[(2-methyl-4-quinolinyl)methoxy]phenyl}acetamideYield 15.9%

Procedure

Commercially available (+/−)-2-amino-2-methyl-pentanedioic acid (1.00 g, 6.8 mmol) was dissolved in 10 mL boiling water and treated portionwise with potassium cyanate (1.20 g, 14.8 mmol). After 15 min, 10% aq HCl (15 mL) was added and the reaction refluxed for 30 min after which the solvent was evaporated off and the white solid filtered, washed with cold water, and dried to give 870 mg (75%) of hydantoin derivative. MS found:(M+H)+=173. (103b) 5-methylhydantoin-5-acetic acid (50 mg, 0.30 mmol) and 4-[(2-methyl-4-quinolinyl)methoxy]-aniline bis-HCl salt (101 mg, 0.30 mmol) were coupled using general coupling method A to give 20 mg (13%) of the product hydantoin. MS found:(M+H)+=419.

Sources & evidence

ORD record
ord-21cf08cd44da437b9f432ec65419340c
Source dataset
uspto-grants-2009_01
Patent number
US07482372B2

Reaction notes

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