Chlorotrimethylsilane → 1-((4-Cyano-2-fluorophenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517208Notes

Reaction equation

HRID 517208 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.[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[CH:23]=O)[C:18]#[N:19].[F:25][C:26]([F:38])([F:37])[C:27]1[CH:28]=[C:29]([NH:33][C:34]([NH2:36])=[O:35])[CH:30]=[CH:31][CH:32]=1>CN(C)C=O.C(#N)C>[C:18]([C:17]1[CH:20]=[CH:21][C:22]([CH:23]([C:7]2[C:8](=[O:12])[CH2:9][CH2:10][CH2:11][C:6]=2[OH:13])[NH:36][C:34]([NH:33][C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([C:26]([F:25])([F:37])[F:38])[CH:28]=2)=[O:35])=[C:15]([F:14])[CH:16]=1)#[N:19]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 104341,3-CyclohexanedioneHCID 25712(3-Trifluoromethylphenyl)ureaHCID 27831503-Fluoro-4-formylbenzonitrile

Product 1

HCID 867323291-((4-Cyano-2-fluorophenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl chloride (1 M in dichloromethane, 4.90 mL, 4.90 mmol) is added to a solution of cyclohexane-1,3-dione (0.50 g, 4.46 mmol), 3-fluoro-4-formylbenzonitrile (0.67 g, 4.46 mmol) and 1-(3-(trifluoromethyl)phenyl)urea (0.91 g, 4.46 mmol) in a mixture of N,N-dimethylformamide (2.0 mL) and acetonitrile (2.0 mL). The mixture is stirred at room temperature for 45 min and then poured into ice water. The mixture is stirred over night at room temperature, and the precipitate is filtered and dried. Yield: 1.8 g; ESI mass spectrum [M+H]+=448, Retention time HPLC: 1.02 min (Z018_S04).

Workup

  1. stirringThe mixture is stirred over night at room temperature
  2. filtrationthe precipitate is filtered
  3. customdried
  4. custom1.02 min (Z018_S04)

Sources & evidence

ORD record
ord-787f5c13d0ab4c39a6a5412e78cef0f7
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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