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

HRID 517193
노트
인쇄 미리보기

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HRID 517193 반응식
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]
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8

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

생성물 1

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

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4842f624e4334fa785a3945169b6ae68
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115093B2

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