Sodium Bicarbonate → HCID 178456892、化合物

HRID 1620512ノート

反応式

HRID 1620512 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 178456892HCID 178456892、化合物収率 15.4%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-31d68afab5d34402b880e415b0d602da
出典データセット
uspto-grants-2014_07
特許番号
US08772277B2

反応ノート

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