Trifluoromethanesulfonic acid → 1-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-5-methylimidazolidine-2,4-dione

HRID 2411801Notes

Reaction equation

[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]([CH3:28])[C:26](=[O:29])[N:25](CC5C=CC(OC)=CC=5)[C:24]4=[O:39])=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>ClCCCl>[CH3:1][C:2]1[C:3]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]([CH3:28])[C:26](=[O:29])[NH:25][C:24]4=[O:39])=[CH:19][CH:18]=3)=[O:16])[CH2:13][CH2:14]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-3-(4-methoxybenzyl)-5-methylimidazolidine-2,4-dione (172 mg) described in Example 448 was dissolved in 1,2-dichloroethane (5 mL), trifluoromethanesulfonic acid (0.18 mL) was added, and the mixture was stirred at 80° C. for 30 min. To the reaction mixture was added 5% aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform/methanol (10:1). The organic layer was dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol) to give the title compound (92 mg).

Workup

extractionthe mixture was extracted with chloroform/methanol (10:1)
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was evaporated
customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol)

Sources & evidence

ORD record: ord-a527bfe071e04bc093fe69d8191c8a95
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816079B2

Reaction notes

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