Water → 1-((5-Cyanopyridin-2-yl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517197Notes

Reaction equation

HRID 517197 reaction equation
C[Si](Cl)(C)C.[CH:6]([C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=1)=O.[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([NH:24][C:25]([NH2:27])=[O:26])[CH:21]=[CH:22][CH:23]=1.[OH2:30].CN(C)[CH:33]=[O:34]>C(#N)C>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([CH:6]([C:8]2[C:15](=[O:30])[CH2:14][CH2:11][CH2:10][C:33]=2[OH:34])[NH:27][C:25]([NH:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:28])([F:29])[F:16])[CH:19]=2)=[O:26])=[N:9][CH:10]=1)#[N:13]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 25712(3-Trifluoromethylphenyl)ureaHCID 213641446-Formylpyridine-3-carbonitrile

Product 1

HCID 867323171-((5-Cyanopyridin-2-yl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl chloride (125 μL, 0.98 mmol) is added to a solution of cyclohexane-1,3-s dione (100 mg, 0.89 mmol), 6-formylnicotinonitrile (118 mg, 0.89 mmol) and 1-(3-(trifluoromethyl)phenyl)urea (182 mg, 0.89 mmol) in a mixture of N,N-dimethyl-formamide (670 μL) and acetonitrile (1.2 mL), and the mixture is stirred at room temperature for 1.5 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: 330 mg; ESI mass spectrum [M+H]+=431, Retention time HPLC: 0.63 min (V011_S01).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationThe mixture is filtered
  3. washthe precipitate is washed with water
  4. customdried under reduced pressure
  5. custom0.63 min (V011_S01)

Sources & evidence

ORD record
ord-98cd3d6ef57146939d054ecc601125f6
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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