Diethyl Ether → 5,5-Dimethyl-3-[6-({3-[(trifluoromethyl)oxy]phenyl}oxy)-3-pyridinyl]-2,4-imidazolidinedione

HRID 1505427Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=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])[NH:22][C:21](=[O:28])[N:20]([C:17]2[CH:18]=[N:19][C:14]([O:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:11])([F:12])[F:1])[CH:5]=3)=[CH:15][CH:16]=2)[C:24]1=[O:25]

Participants

Conditions

Temperature: 120 °C

Procedure

3-[(trifluoromethyl)oxy]phenol (19.95 mg, 0.112 mmol) was dissolved in 1 mL of dimethylformamide. 3-(6-fluoro-3-pyridinyl)-5,5-dimethyl-2,4-imidazolidinedione (Intermediate 106, 25 mg) and potassium carbonate (31.0 mg, 0.224 mmol) were added. The reaction mixture was stirred at 120° C. during 22 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 I). 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 as a white solid (23 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 I)
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-c8272bbd3ed64f5ab27b65bc532f101b
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216967B2

Reaction notes

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