Ethanol → N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide

HRID 1026224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026224
C([N:8]1[C:12]([C:13]2[O:14][C:15]3[CH:21]=[C:20]([O:22][CH2:23][CH:24]4[CH2:26][CH2:25]4)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:11][C:10]([O:27][CH2:28][C@@H:29]([NH:31][C:32](=[O:34])[CH3:33])[CH3:30])=[N:9]1)C1C=CC=CC=1.C(O)C>[OH-].[OH-].[Pd+2].C1COCC1>[CH:24]1([CH2:23][O:22][C:20]2[CH:19]=[CH:18][C:16]3[N:17]=[C:13]([C:12]4[NH:8][N:9]=[C:10]([O:27][CH2:28][C@@H:29]([NH:31][C:32](=[O:34])[CH3:33])[CH3:30])[CH:11]=4)[O:14][C:15]=3[CH:21]=2)[CH2:25][CH2:26]1

Komponenten

5

Edukt 2

HCID 702EthanolHCID 67778187HCID 67778187, Verbindung

Produkt 1

HCID 67777673N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamideAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Under a hydrogen atmosphere, a mixture of N-[(1S)-2-({1-benzyl-5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide (120 mg), 20% palladium hydroxide/carbon (containing water (50%), 60 mg), ethanol (5 mL) and THF (3 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) to give the title compound (23.4 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)

Quellen und Nachweise

ORD-Eintrag
ord-bb33dedafc3544a2af69efa787e0fd09
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729102B2

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