Methanol → 1-[3-Fluoro-4-(2,2,2-trifluoroacetyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80264

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])[C:15]2=[O:26])[CH:5]=[CH:6][C:7]=1[CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10].CO>C(Cl)Cl.O=[Mn]=O>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH2:17][N:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])[C:15]2=[O:26])[CH:5]=[CH:6][C:7]=1[C:8](=[O:13])[C:9]([F:12])([F:10])[F:11]

Participants

Conditions

Temperature: 50 °C

Procedure

MnO2 (536 mg, 6.165 mmol) was added to 1-[3-fluoro-4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-197a: 325 mg, 0.880 mmol) in DCM (20 mL) under nitrogen atmosphere. The resulting suspension was stirred at 50° C. overnight. The reaction was monitored by TLC (5% MeOH in DCM). The reaction mixture was cooled to room temperature and filtered through celite pad. The filtrate was washed with CHCl3, dried over Na2SO4 and concentrated. The concentrate was washed with hexane and dried to afford 240 mg of the product (74.53% yield).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through celite pad
washThe filtrate was washed with CHCl3
dry with materialdried over Na2SO4
concentrationconcentrated
washThe concentrate was washed with hexane
customdried

Sources & evidence

ORD record: ord-671ad7d54fac432a972bf68e36093e81
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE045173E1

Linked notes

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