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

HRID 2070020노트

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HRID 2070020 반응식
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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 178418390HCID 178418390, 화합물촉매HCID 313Hydrochloric Acid용매HCID 887Methanol용매

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온도
50 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-864386531d6748eea330dadf30c43f18
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299252B2

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