Sodium Bicarbonate → HCID 178456892, 화합물

HRID 1620512노트

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HRID 1620512 반응식
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH2:13][CH:12]2[CH2:14][CH:8]([CH2:9][CH:10]([CH:15]=O)[CH2:11]2)[CH2:7]1.[CH2:27]([NH:30][C:31]1[CH2:35][S:34][C:33](=[O:36])[N:32]=1)[C:28]#[CH:29].C([O-])(=O)C.[NH2+]1CCCCC1.C(=O)([O-])O.[Na+]>CC(O)C>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH2:7][CH:8]2[CH2:14][CH:12]([CH2:11][CH:10](/[CH:15]=[C:35]3/[C:31]([NH:30][CH2:27][C:28]#[CH:29])=[N:32][C:33](=[O:36])[S:34]/3)[CH2:9]2)[CH2:13]1

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 3014295Piperidinium acetateHCID 866787043-[2,4-Bis(trifluoromethyl)benzyl]-3-azabicyclo[3.3.1]nonane-7-carbaldehydeHCID 178456890HCID 178456890, 화합물

생성물 1

HCID 178456892HCID 178456892, 화합물수율 15.4%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
60 °C

실험 절차

To a solution of 3-[2,4-bis(trifluoromethyl)benzyl]-3-azabicyclo[3.3.1]nonane-7-carbaldehyde (173.9 mg) and 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (141 mg) in 2-propanol (2.29 mL) was added piperidinium acetate (66.6 mg). The reaction mixture was stirred at 60° C. overnight, allowed to cool to room temperature, poured into saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (36.4 mg).

후처리

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  7. customrecrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-31d68afab5d34402b880e415b0d602da
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772277B2

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