Methanol → N-[(1S)-3-{6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}-1-methylpropyl]acetamide

HRID 1026288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026288
[CH:1]1([CH2:4][O:5][C:6]2[CH:28]=[CH:27][C:9]3[N:10]=[C:11]([C:13]4[N:18]=[CH:17][C:16]([C:19]#[C:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:15][CH:14]=4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.CO>[Pd].C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:28]=[CH:27][C:9]3[N:10]=[C:11]([C:13]4[N:18]=[CH:17][C:16]([CH2:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:15][CH:14]=4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 887MethanolHCID 67778473HCID 67778473, Verbindung

Produkt 1

HCID 67776829N-[(1S)-3-{6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}-1-methylpropyl]acetamideAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Under a hydrogen atmosphere, a mixture of N-[(1S)-3-{6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}-1-methylprop-2-yn-1-yl]acetamide (98.0 mg), 10% palladium/carbon (containing water (50%), 19.6 mg), methanol (5 mL) and THF (1 mL) was stirred at 50° C. for 4 hr. The catalyst was removed by filtration, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol) to give the title compound as yellow crystals (37.0 mg).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-98f8612c50ca43e7a744d04b02ff1160
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729102B2

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