HCID 117601197, Verbindung → HCID 117602002, Verbindung

HRID 1773748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773748
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:17]([O:19]C)=O)[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:21])[O:4][N:3]=1.[CH:22]([Mg]Br)([CH3:24])[CH3:23]>C1COCC1>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:17](=[O:19])[CH:22]([CH3:24])[CH3:23])[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:21])[O:4][N:3]=1

Komponenten

4

Edukt 2

HCID 117601197HCID 117601197, VerbindungHCID 178418365HCID 178418365, Verbindung

Produkt 1

HCID 117602002HCID 117602002, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate (100 mg, 0.35 mmol) was dissolved in 5 mL of THF and stirred at room temperature followed by the addition of isopropylmagnesium bromide (0.87 mL, 2.0 mmol). Addition Grignard was added in 1 hour intervals until the starting material was consumed. Once complete, the crude reaction mixture was quenched with DI water and extracted 3× with ethyl acetate. Combined organic layers were washed with brine, dried over sodium sulphate, filtered, concentrated in vacuo, and purified via HPLC.

Aufarbeitung

  1. additionAddition Grignard
  2. additionwas added in 1 hour intervals until the starting material
  3. customwas consumed
  4. customOnce complete, the crude reaction mixture
  5. customwas quenched with DI water
  6. extractionextracted 3× with ethyl acetate
  7. washCombined organic layers were washed with brine
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. custompurified via HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a8df114929634879bdd3c65ea1c83ebf
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255089B2

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