Trifluoroacetic anhydride → N-[5-[4,4-dimethyl-2,5-dioxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl]-2-(trifluoromethoxy)phenyl]-2,2,2-trifluoroacetamide;2,2,2-trifluoroacetic acid

HRID 2356955Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[N:15]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[C:14]2=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[F:29][C:30]([F:41])([F:40])[C:31]([O:33][C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])=[O:32]>ClCCl.N1C=CC=CC=1>[F:29][C:30]([F:41])([F:40])[C:31]([OH:33])=[O:32].[CH3:19][C:16]1([CH3:20])[C:17](=[O:18])[N:13]([C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]([F:11])([F:10])[F:12])=[C:2]([NH:1][C:34](=[O:39])[C:35]([F:36])([F:37])[F:38])[CH:3]=2)[C:14](=[O:28])[N:15]1[CH2:21][C:22]1[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

394 mg (1.0 mmol) of 3-(3-amino-4-trifluoromethoxyphenyl)-5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dione were dissolved in 5 ml of 4:1 dichloromethane/pyridine and cooled to 0° C., and 252 mg (1.2 mmol) of trifluoroacetic anhydride dissolved in 5 ml of 4:1 dichloromethane/pyridine were added dropwise at 0° C. After stirring at RT, the mixture was added to ice-water, extracted with CH2Cl2, concentrated and dried. The remaining residue was purified by means of preparative HPLC (RP18, acetonitrile/water, 0.1% TFA).

Workup

additionwere added dropwise at 0° C
extractionextracted with CH2Cl2
concentrationconcentrated
customdried
customThe remaining residue was purified by means of preparative HPLC (RP18, acetonitrile/water, 0.1% TFA)

Sources & evidence

ORD record: ord-606b22cbcd2c429388da196473a99e98
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759379B2

Reaction notes

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