(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 571982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571982
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 712372781-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)ureaAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8ea548b26fb347db8cbb91ce92d88ae1
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029378B2

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