Chlorotrimethylsilane → 1-((4-Cyanophenyl)(2-hydroxy-6-oxo-4-(thiophen-2-yl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517189Notes

Reaction equation

HRID 517189 reaction equation
C[Si](Cl)(C)C.[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]1[CH2:16][C:15](=[O:17])[CH2:14][C:13](=[O:18])[CH2:12]1.[CH:19]([C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)=O.[F:29][C:30]([F:42])([F:41])[C:31]1[CH:32]=[C:33]([NH:37][C:38]([NH2:40])=[O:39])[CH:34]=[CH:35][CH:36]=1>CN(C)C=O.C(#N)C.O>[C:25]([C:24]1[CH:27]=[CH:28][C:21]([CH:19]([C:14]2[C:15](=[O:17])[CH2:16][CH:11]([C:7]3[S:6][CH:10]=[CH:9][CH:8]=3)[CH2:12][C:13]=2[OH:18])[NH:40][C:38]([NH:37][C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([C:30]([F:41])([F:42])[F:29])[CH:32]=2)=[O:39])=[CH:22][CH:23]=1)#[N:26]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 5736855-(2-Thienyl)cyclohexane-1,3-dione

Product 1

HCID 867323081-((4-Cyanophenyl)(2-hydroxy-6-oxo-4-(thiophen-2-yl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl chloride (216 μL, 1.70 mmol) is added to a solution of 5-(thiophen-2-yl)-cyclohexane-1,3-dione (300 mg, 1.54 mmol), 4-formylbenzonitrile (202 mg, 1.54 mmol) and 1-(3-(trifluoromethyl)phenyl)urea (315 mg, 1.54 mmol) in a mixture of N,N-dimethyl-formamide (1.2 mL) and acetonitrile (2.3 mL). The mixture is stirred at room temperature over night and poured into a mixture of water and ice. The precipitate is filtered and dried under reduced pressure. Yield: 444 mg; ESI mass spectrum [M+H]+=512, Retention time HPLC: 0.75 min (V011_S01).

Workup

  1. filtrationThe precipitate is filtered
  2. customdried under reduced pressure
  3. custom0.75 min (V011_S01)

Sources & evidence

ORD record
ord-06ef322314ef4043b0772c2ff0f5e74a
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

Loading…