Methyl iodide → 3-[(E)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one

HRID 2206859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2206859
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[C:12]2[NH:16][C:15](=[O:17])[O:14][N:13]=2)[CH:5]=[CH:4][CH:3]=1.[C:24](=O)([O-])[O-].[K+].[K+].IC>CC#N.CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[C:12]2[N:16]([CH3:24])[C:15](=[O:17])[O:14][N:13]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1366263643-[(Z)-N-[(6-amino-2-pyridinyl)methoxy]-C-phenylcarbonimidoyl]-4H-1,2,4-oxadiazol-5-one

Produkt 1

HCID 894438773-[(E)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-oneAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 3-[(Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-1,2,4-oxadiazol-5(4H)-one (1 g, 3.21 mmol, 1 eq.) in MeCN (50 ml) and DMF (10 ml) was added potassium carbonate (532 mg, 3.85 mmol, 1.2 eq.) followed by iodomethane (547 mg, 3.85 mmol, 1.2 eq.). The reaction was stirred at room temperature overnight. The reaction was quenched by addition of water and extracted with EtOAc (3×50 ml). The organics were combined, washed with aq. sat. NaCl, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one (906 mg, 85% yield) has a white solid.

Aufarbeitung

  1. customThe reaction was quenched by addition of water
  2. extractionextracted with EtOAc (3×50 ml)
  3. washwashed with aq. sat. NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c3e29ded53464c6984d9ff8c7e414d39
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09375010B2

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