4-(1-benzyloxymethyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline → 4-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline

HRID 2070020ノート

反応式

HRID 2070020 の反応式
C(OC[N:10]1[C:14]2=[N:15][CH:16]=[CH:17][C:18]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)=[C:13]2[CH:12]=[N:11]1)C1C=CC=CC=1>CO.Cl.[C].[Pd]>[NH:10]1[C:14]2=[N:15][CH:16]=[CH:17][C:18]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)=[C:13]2[CH:12]=[N:11]1

参加物

5

反応物 1

HCID 593985194-(1-benzyloxymethyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline

生成物 1

HCID 593985424-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline収率 25.4%

試薬・触媒・溶媒 3

HCID 178418390HCID 178418390、化合物触媒HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

4-(1-Benzyloxymethyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline (140 mg, 0.40 mmol) was dissolved in methanol (5 mL) and 5 N hydrochloric acid (0.2 mL), and palladium carbon (10%, 10 mg) was added thereto. The resulting mixture was stirred at 50° C. for 4 hours under a hydrogen atmosphere. The catalyst was removed by filtration, and the methanol solution was concentrated. The residue was neutralized with a 5 N sodium hydroxide aqueous solution (0.2 mL) and partitioned between saturated brine (3 mL) and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by amino-silica gel (Fuji Silysia, 5 g, ethyl acetate) to give 4-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline (23 mg, yield: 25%).

後処理

  1. customThe catalyst was removed by filtration
  2. concentrationthe methanol solution was concentrated
  3. custompartitioned between saturated brine (3 mL) and ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by amino-silica gel (Fuji Silysia, 5 g, ethyl acetate)

出典と根拠

ORDレコード
ord-864386531d6748eea330dadf30c43f18
出典データセット
uspto-grants-2012_10
特許番号
US08299252B2

反応ノート

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