Chlorotrimethylsilane → 1-((4-Cyanophenyl)(8-hydroxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517179Notes

Reaction equation

HRID 517179 reaction equation
C[Si](Cl)(C)C.[CH2:6]1[C:11]2([CH2:16][C:15](=[O:17])[CH2:14][C:13](=[O:18])[CH2:12]2)[CH2:10][CH2:9][O:8][CH2:7]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][C:11]3([CH2:10][CH2:9][O:8][CH2:7][CH2:6]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 666800033-Oxaspiro[5.5]undecane-8,10-dione

Product 1

HCID 867322991-((4-Cyanophenyl)(8-hydroxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Trimethylsilyl chloride (275 μL, 2.17 mmol) is added to a solution of 3-oxaspiro[5.5]un-decane-8,10-dione (360 mg, 1.98 mmol), 4-formylbenzonitrile (259 mg, 1.98 mmol) and 1-(3-(trifluoromethyl)phenyl)urea (403 mg, 1.98 mmol) in a mixture of N,N-dimethyl-formamide (1.5 mL) and acetonitrile (2.5 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 precipitate is filtered and dried under reduced pressure. Yield: 712 mg; ESI mass spectrum [M+H]+=500, Retention time HPLC: 1.12 min (V012_S01).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationThe precipitate is filtered
  3. customdried under reduced pressure
  4. custom1.12 min (V012_S01)

Sources & evidence

ORD record
ord-addb74a2d7694404a6c3884650b2129a
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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