Water → HCID 68294990, Verbindung

HRID 1854055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854055
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]2[CH:24]=[N:23][N:22]([CH:25]([CH3:27])[CH3:26])[C:16]=2[N:17]=[C:18]([CH:20]=[CH2:21])[CH:19]=1)=[O:13].C[N+]1([O-])CCOCC1.[OH2:36].C[OH:38].C(Cl)Cl>C(Cl)Cl.O=[Os](=O)(=O)=O>[OH:36][CH:20]([C:18]1[CH:19]=[C:14]([C:12]([NH:11][CH2:10][C:3]2[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[O:13])[C:15]2[CH:24]=[N:23][N:22]([CH:25]([CH3:27])[CH3:26])[C:16]=2[N:17]=1)[CH2:21][OH:38]

Komponenten

7

Edukt 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 21226129Dichloromethane methanolHCID 68294850HCID 68294850, Verbindung

Produkt 1

HCID 68294990HCID 68294990, VerbindungAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-vinyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.8 g, 2.19 mmol) in DCM (10 mL), N-Methylmorpholine-N-oxide (0.769 g, 6.57 mmol) was added at 0° C. Then OsO4 (2.5% in t-BuOH) (0.139 g, 5.56 mL, 0.547 mmol) was added to it. Resulting solution was stirred at room temperature for 1 h. After completion of reaction, water was added to it and extraction was carried out using 20% MeOH/DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography to give the desired product (0.66 g, 75.4%).

Aufarbeitung

  1. additionwas added to it and extraction
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude material which
  7. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-64521e947d8f4b0795c1ad5d05b78497
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962620B2

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