Pyridine → 3-((E)-4-((E)-2-Phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)styryl)-1,2,4-oxadiazol-5(4H)-one

HRID 1057202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057202
[OH:1]/[N:2]=[C:3](\[NH2:37])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[N:26]=[CH:25]3)=[C:13](\[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)/[CH2:14][CH3:15])=[CH:8][CH:7]=1.C(C(CCCC)[CH2:41][O:42]C(Cl)=O)C.N1C=CC=CC=1>CN(C=O)C>[C:16]1(/[C:13](/[CH2:14][CH3:15])=[C:12](\[C:9]2[CH:8]=[CH:7][C:6](/[CH:5]=[CH:4]/[C:3]3[NH:37][C:41](=[O:42])[O:1][N:2]=3)=[CH:11][CH:10]=2)/[C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[N:26]=[CH:25]3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 627832-Ethylhexyl chloroformateHCID 87765319(E)-N'-hydroxy-3-[4-[(E)-1-[1-(oxan-2-yl)indazol-5-yl]-2-phenylbut-1-enyl]phenyl]prop-2-enimidamide

Produkt 1

HCID 1364057393-((E)-4-((E)-2-Phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)styryl)-1,2,4-oxadiazol-5(4H)-oneAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (1Z,2E)-N′-hydroxy-3-(4-((E)-2-phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylimidamide (51 mg, 0.1 mmol) in anhydrous DMF (0.4 mL) was added 2-ethylhexylchloroformate (20 μL, 0.1 mmol) followed by pyridine (9 μL, 0.11 mmol). The reaction mixture was stirred at 0° C. for 1 h and then partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (2×), and the combined organics were dried over MgSO4 and concentrated. The residue was dissolved in xylenes (1 mL), heated at 130° C. for 2 h, and then concentrated to afford 25 mg of the title compound. LCMS: 519 (M+H)+.

Aufarbeitung

  1. custompartitioned between water and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc (2×)
  3. dry with materialthe combined organics were dried over MgSO4
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in xylenes (1 mL)
  6. temperatureheated at 130° C. for 2 h
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8a980713ba404a6d9e104b605f826c39
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399646B2

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