Acetonitrile → 2-(1-(Methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-5-((1-(2,2,2-trifluoroethyl)piperidin-4-yl)methoxy)pyridine

HRID 222598노트

반응식

HRID 222598 반응식
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=C[C:19]([C:22]3[CH2:23][CH2:24][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:26][CH:27]=3)=[CH:18][C:17]=2F)[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:45][C:46]([F:49])([F:48])[F:47])(=O)=O.C(#[N:54])C>O>[CH3:31][S:28]([N:25]1[CH2:26][CH:27]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH:11]3[CH2:10][CH2:9][N:8]([CH2:45][C:46]([F:49])([F:48])[F:47])[CH2:13][CH2:12]3)=[CH:21][N:54]=2)[CH2:23][CH2:24]1)(=[O:30])=[O:29]

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 668644984-[2-Fluoro-4-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 581111682-(1-(Methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-5-((1-(2,2,2-trifluoroethyl)piperidin-4-yl)methoxy)pyridine

시약·촉매·용매 1

HCID 962Water용매

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온도
85 °C

실험 절차

To a solution of Preparation 6 (0.05 g, 0.14 mmol) in acetonitrile (1.50 mL) are added potassium carbonate (0.07 g, 0.56 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.06 g, 0.28 mmol). The reaction mixture is heated at 85° C. for 1 h in a microwave, cooled to room temperature and diluted with water. The mixture is extracted with ethyl acetate and the combined organic extracts are dried over sodium sulfate, filtered, and concentrated. The residue is purified by flash column chromatography over silica gel to obtain 30 mg of the title compound as an off-white solid. MS (m/z) 433 (M+1).

후처리

  1. temperaturecooled to room temperature
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe combined organic extracts are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash column chromatography over silica gel

출처 및 근거

ORD 기록
ord-aec94733a5024d29887fcaa3cd68f965
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207344B2

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