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Chlorotrimethylsilane → 1-((4-Cyanophenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(4-(trifluoromethyl)pyridin-2-yl)urea

HRID 517193
Notes
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Reaction equation

HRID 517193 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]=[CH:30][N:29]=[C:28]([NH:32][C:33]([NH2:35])=[O:34])[CH: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:28]2[CH:27]=[C:26]([C:25]([F:36])([F:24])[F:37])[CH:31]=[CH:30][N:29]=2)=[O:34])=[CH:17][CH:18]=1)#[N:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 104341,3-CyclohexanedioneHCID 660424-CyanobenzaldehydeHCID 692857421-(4-(Tri-fluoromethyl)pyridin-2-yl)urea

Product 1

HCID 867323121-((4-Cyanophenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(4-(trifluoromethyl)pyridin-2-yl)urea

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Trimethylsilyl chloride (125 μL, 0.982 mmol) is added to a solution of cyclohexane-1,3-dione (100 mg, 0.892 mmol), 4-formylbenzonitrile (117 mg, 0.892 mmol) and 1-(4-(tri-fluoromethyl)pyridin-2-yl)urea (183 mg, 0.892 mmol) in a mixture of N,N-dimethylformamide (670 μL) and acetonitrile (1.2 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 mixture is filtered, and the precipitate is washed with water and dried under reduced pressure. Yield: 293 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-4842f624e4334fa785a3945169b6ae68
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115093B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes