Sodium Hydroxide → 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 2279139ノート

反応式

HRID 2279139 の反応式
C([O:3][C:4]([C:6]1[C:7]2[C:24]([CH3:25])=[N:23][N:22]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:8]=2[N:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][O:20][CH3:21])=[CH:14][CH:13]=2)[CH:11]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:21][O:20][CH2:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]3[C:24]([CH3:25])=[N:23][N:22]([CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][O:27]4)[C:8]=3[N:9]=2)=[CH:13][CH:14]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 900137956-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

生成物 1

HCID 900138076-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid収率 90%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To 2.09 g 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester in 140 ml ethanol was added 100 ml of 1M aqueous sodium hydroxide solution. After 3 h at r.t. the volatiles were removed in vacuo. The residue was taken up in water and the pH was adjusted to 4-5. The aqueous phase was extracted with ethyl acetate three times. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, dichloromethane/MeOH gradient with addition of aqueous ammonia) to obtain 1.74 g (90%) of the title compound.

後処理

  1. customAfter 3 h at r.t. the volatiles were removed in vacuo
  2. extractionThe aqueous phase was extracted with ethyl acetate three times
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica, dichloromethane/MeOH gradient with addition of aqueous ammonia)

出典と根拠

ORDレコード
ord-fc42d8a68d8d43238dd7a9b18b80da58
出典データセット
uspto-grants-2015_09
特許番号
US09133181B2

反応ノート

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