4-Chloro-2-methylpyridine hydrochloride → HCID 66805338, Verbindung

HRID 1193350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193350
[C:1]([N:8]([CH3:13])[CH:9]1[CH2:12][NH:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[CH:17]=1>CC(O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:13][N:8]([CH:9]1[CH2:12][N:11]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[CH:17]=2)[CH2:10]1)[C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5]

Komponenten

6

Edukt 2

HCID 27628414-Chloro-2-methylpyridine hydrochlorideHCID 23033645tert-Butyl azetidin-3-yl(methyl)carbamate

Produkt 1

HCID 66805338HCID 66805338, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

3-(Boc-methylamino)azetidine (2.74 mmol, 1.0 eq) and 4-chloro-2-methylpyridine HCl (8.21 mmol, 3.0 eq) were dissolved in 2-propanol (5 ml) and DI PEA (13.69 mmol. 5.0 eq) and refluxed for 24 hours. After monitoring by TLC, the reaction solution was diluted with ethyl acetate and sat. sodium hydrogen carbonate solution, and the phases were separated. The aqueous phase was washed with ethyl acetate. The combined organic phases were washed 1× with sat. NaCl solution, dried over magnesium sulfate, concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia solution). Yield: 51%

Aufarbeitung

  1. temperatureDI PEA (13.69 mmol. 5.0 eq) and refluxed for 24 hours
  2. customthe phases were separated
  3. washThe aqueous phase was washed with ethyl acetate
  4. washThe combined organic phases were washed 1× with sat. NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia solution)

Quellen und Nachweise

ORD-Eintrag
ord-749c85f60e9e44dca116dd0ffefe3af8
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680159B2

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