Sodium Hydroxide → 4-(4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylic acid

HRID 2206018ノート

反応式

HRID 2206018 の反応式
[O:1]=[C:2]1[C:7]2[C:8]([C:17]3[CH:18]=[C:19]([C:22]([O:24]C)=[O:23])[S:20][CH:21]=3)=[N:9][N:10]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=[CH:4][NH:3]1.[OH-].[Na+]>CO>[O:1]=[C:2]1[C:7]2[C:8]([C:17]3[CH:18]=[C:19]([C:22]([OH:24])=[O:23])[S:20][CH:21]=3)=[N:9][N:10]([CH:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[C:6]=2[CH:5]=[CH:4][NH:3]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 137010801methyl 4-(4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylate

生成物 1

HCID 1370106064-(4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylic acid収率 99.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of methyl 4-(4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylate (125 mg) obtained in Example 21 in methanol (20 mL) was added 1N aqueous sodium hydroxide solution (5 mL) under ice-cooling, and the mixture was stirred at 50° C. for 6 hr. The reaction mixture was concentrated under reduced pressure to evaporate the methanol, and the residue was partitioned between ethyl acetate and 1N hydrochloric acid (6 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (119 mg).

後処理

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto evaporate the methanol
  4. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid (6 mL)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-45468782c95d468292899ffdfef794d2
出典データセット
uspto-grants-2016_06
特許番号
US09371320B2

反応ノート

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