Diethyl Ether → 4-{[5-(4,4-Dimethyl-2,5-dioxo-1-imidazolidinyl)-2-pyridinyl]oxy}-2-(1-methylethyl)benzonitrile

HRID 1023621Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH:10]([CH3:12])[CH3:11])[CH:3]=1.F[C:14]1[N:19]=[CH:18][C:17]([N:20]2[C:24](=[O:25])[C:23]([CH3:27])([CH3:26])[NH:22][C:21]2=[O:28])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CN(C)C=O.O>[CH3:26][C:23]1([CH3:27])[C:24](=[O:25])[N:20]([C:17]2[CH:16]=[CH:15][C:14]([O:1][C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH:10]([CH3:12])[CH3:11])[CH:3]=3)=[N:19][CH:18]=2)[C:21](=[O:28])[NH:22]1

Participants

Conditions

Temperature: 120 °C

Procedure

4-hydroxy-2-(1-methylethyl)benzonitrile (30 mg) was dissolved in 1 mL of dimethylformamide. 3-(6-fluoro-3-pyridinyl)-5,5-dimethyl-2,4-imidazolidinedione (Intermediate 106, 41.5 mg) and potassium carbonate (51.4 mg, 0.372 mmol) were added. The reaction mixture was stirred at 120° C. during 40 hours. Some diethylether (4 mL) and water (4 mL) were added. The aqueous layer was extracted 4 times with diethylether. The gathered organic layers were dried over sodium sulphate and evaporated giving a residue which was purified by mass directed purification (METHOD H). After evaporation of the fraction, addition of a solution of saturated NaHCO3 (3 mL) and extraction with dichloromethane (four times 4 mL), evaporation afforded the title compound (13 mg).

Workup

extractionThe aqueous layer was extracted 4 times with diethylether
dry with materialThe gathered organic layers were dried over sodium sulphate
customevaporated
customgiving a residue which
customwas purified by mass
custompurification (METHOD H)
customAfter evaporation of the fraction, addition of a solution of saturated NaHCO3 (3 mL) and extraction
customwith dichloromethane (four times 4 mL), evaporation

Sources & evidence

ORD record: ord-e79eeb3fbcb245bba71f7016187cebbd
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722695B2

Reaction notes

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