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Chlorotrimethylsilane → 1-((6-Cyanopyridin-3-yl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517199
노트
인쇄 미리보기

반응식

HRID 517199 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:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=1)=O.[F:24][C:25]([F:37])([F:36])[C:26]1[CH:27]=[C:28]([NH:32][C:33]([NH2:35])=[O:34])[CH:29]=[CH:30][CH:31]=1>CN(C)C=O.C(#N)C.O>[C:22]([C:19]1[N:20]=[CH:21][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:29]=[CH:30][CH:31]=[C:26]([C:25]([F:24])([F:36])[F:37])[CH:27]=2)=[O:34])=[CH:17][CH:18]=1)#[N:23]
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참가 물질

8

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 104341,3-CyclohexanedioneHCID 25712(3-Trifluoromethylphenyl)ureaHCID 109862635-Formylpyridine-2-carbonitrile

생성물 1

HCID 867323191-((6-Cyanopyridin-3-yl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)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), 5-formylpicolinonitrile (118 mg, 0.892 mmol) and 1-(3-(tri-fluoromethyl)phenyl)urea (183 mg, 0.829 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: 346 mg; ESI mass spectrum [M+H]+=431, Retention time HPLC: 0.67 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. custom0.67 min (V011_S01)

출처 및 근거

ORD 기록
ord-dbe772e04a10423da02d70b56c99b219
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115093B2

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