Chlorotrimethylsilane → HCID 86732314, compound

HRID 517195Notes

Reaction equation

HRID 517195 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:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1)=O.[F:24][C:25]([F:37])([F:36])[C:26]1[CH:31]=[C:30]([NH:32][C:33]([NH2:35])=[O:34])[CH:29]=[CH:28][N:27]=1>CN(C)C=O.C(#N)C.O>[C:20]([C:19]1[CH:22]=[CH:23][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:30]2[CH:29]=[CH:28][N:27]=[C:26]([C:25]([F:24])([F:36])[F:37])[CH:31]=2)=[O:34])=[CH:17][CH:18]=1)#[N:21]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 104341,3-CyclohexanedioneHCID 660424-CyanobenzaldehydeHCID 86732315HCID 86732315, compound

Product 1

HCID 86732314HCID 86732314, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl chloride (187 μL, 1.47 mmol) is added to a solution of cyclohexane-1,3-dione (150 mg, 1.34 mmol), 4-formylbenzonitrile (175 mg, 1.34 mmol) and 1-(2-(trifluoromethyl)pyridin-4-yl)urea (274 mg, 1.34 mmol) in a mixture of N,N-dimethyl-formamide (1.0 mL) and acetonitrile (1.8 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: 410 mg; ESI mass spectrum [M+H]+=431, Retention time HPLC: 0.60 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. custom0.60 min (V011_S01)

Sources & evidence

ORD record
ord-8e11b4c8992c47889a2236b7437a6b5a
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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