Chlorotrimethylsilane → 1-((6-Cyanopyridin-3-yl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517199Notes

Reaction equation

C[Si](Cl)(C)C.[C:6]1(=[O:13])[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[CH2:7]1.[CH:14]([C:16]1[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=1)=O.[F:24][C:25]([F:37])([F:36])[C:26]1[CH:27]=[C:28]([NH:32][C:33]([NH2:35])=[O:34])[CH:29]=[CH:30][CH:31]=1>CN(C)C=O.C(#N)C.O>[C:22]([C:19]1[N:20]=[CH:21][C:16]([CH:14]([C:7]2[C:8](=[O:12])[CH2:9][CH2:10][CH2:11][C:6]=2[OH:13])[NH:35][C:33]([NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:24])([F:36])[F:37])[CH:27]=2)=[O:34])=[CH:17][CH:18]=1)#[N:23]

Participants

Conditions

Temperature: 50 °C

Procedure

Trimethylsilyl chloride (125 μL, 0.982 mmol) is added to a solution of cyclohexane-1,3-dione (100 mg, 0.892 mmol), 5-formylpicolinonitrile (118 mg, 0.892 mmol) and 1-(3-(tri-fluoromethyl)phenyl)urea (183 mg, 0.829 mmol) in a mixture of N,N-dimethylformamide (670 μL) and acetonitrile (1.2 mL), and the mixture is heated at 50° C. for 1 h. The reaction mixture is cooled to room temperature and poured into a mixture of water and ice. The mixture is filtered, and the precipitate is washed with water and dried under reduced pressure. Yield: 346 mg; ESI mass spectrum [M+H]+=431, Retention time HPLC: 0.67 min (V011_S01).

Workup

temperatureThe reaction mixture is cooled to room temperature
filtrationThe mixture is filtered
washthe precipitate is washed with water
customdried under reduced pressure
custom0.67 min (V011_S01)

Sources & evidence

ORD record: ord-dbe772e04a10423da02d70b56c99b219
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115093B2

Reaction notes

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