(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine → 1-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)urea

HRID 571982노트

반응식

HRID 571982 반응식
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([NH:10][C:11](=[O:19])OC3C=CC=CC=3)[CH:9]=[C:4]2[CH:3]=[N:2]1.[CH3:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=[C:29]([C:35]([F:38])([F:37])[F:36])[N:28]=2)[CH2:23][CH2:22]1>C(#N)C.CN(C1C=CN=CC=1)C>[CH3:20][CH:21]1[CH2:22][CH2:23][N:24]([C:27]2[C:32]([CH2:33][NH:34][C:11]([NH:10][C:8]3[CH:9]=[C:4]4[CH:3]=[N:2][NH:1][C:5]4=[N:6][CH:7]=3)=[O:19])=[CH:31][CH:30]=[C:29]([C:35]([F:38])([F:36])[F:37])[N:28]=2)[CH2:25][CH2:26]1

참가 물질

5

반응물 2

HCID 58873687(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamineHCID 86676322phenyl 1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate

생성물 1

HCID 712372781-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)urea수율 71.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a solution of phenyl 1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate (C) (84 mg, 0.329 mmol) in acetonitrile was added DMAP (40 mg, 0.329 mmol) and (2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine (D) (90 mg, 0.329 mmol) at room temperature. The reaction mixture was heated to 50° C. for 15 h. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude was purified by column chromatography to give pure 1-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)urea (example compound 5) (102 mg, 71%).

후처리

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-8ea548b26fb347db8cbb91ce92d88ae1
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029378B2

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