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

HRID 2356952Notes

Reaction equation

[CH2:1]([N:3](CC)[CH2:4]C)C.[NH2:8][C:9]1[CH:10]=[C:11]([N:20]2[C:24](=[O:25])[C:23]([CH3:27])([CH3:26])[N:22]([CH2:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[C:21]2=[O:35])[CH:12]=[CH:13][C:14]=1[O:15][C:16]([F:19])([F:18])[F:17].[OH2:36].[CH2:37]1[CH2:41][O:40][CH2:39][CH2:38]1>>[F:19][C:16]([F:17])([F:18])[C:41]([OH:40])=[O:36].[CH3:26][C:23]1([CH3:27])[C:24](=[O:25])[N:20]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]([F:17])([F:18])[F:19])=[C:9]([NH:8][C:41](=[O:40])[C:37]3[CH:38]=[CH:39][CH:4]=[N:3][CH:1]=3)[CH:10]=2)[C:21](=[O:35])[N:22]1[CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1

Participants

Reactant 4

HCID 962Water

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 231103083-(3-Amino-4-trifluoromethoxyphenyl)5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dione

Product 1

HCID 86617224N-[5-[4,4-dimethyl-2,5-dioxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl]-2-(trifluoromethoxy)phenyl]pyridine-3-carboxamide;2,2,2-trifluoroacetic acid

Procedure

51 mg (0.51 mmol) of triethylamine and 45 mg (0.25 mmol) of 3-nicotinyl chloride are added to 100 mg (0.25 mmol) of 3-(3-amino-4-trifluoromethoxyphenyl)-5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dione in 5 ml of THF and stirred at RT for 6 h. For workup, the mixture was added to water, extracted with ethyl acetate, dried and concentrated. The remaining residue was purified by means of preparative HPLC (RP18, acetonitrile/water, 0.1% TFA). Yield: 50 mg.

Workup

extractionextracted with ethyl acetate
customdried
concentrationconcentrated
customThe remaining residue was purified by means of preparative HPLC (RP18, acetonitrile/water, 0.1% TFA)

Sources & evidence

ORD record: ord-6ac79da735534562b36aff10c4b61bfe
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759379B2

Reaction notes

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