Potassium Hydroxide → 1-ethyl-6-methoxy-2-[4-(2-oxo-imidazolidin-1-yl)-phenyl]-1H-indole-3-carbonitrile

HRID 907189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907189
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([CH2:27][CH3:28])[C:16]3[C:21]([C:22]=2[C:23]#[N:24])=[CH:20][CH:19]=[C:18]([O:25][CH3:26])[CH:17]=3)=[CH:10][CH:9]=1)=[O:6].[OH-].[K+]>CO>[CH2:27]([N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[C:18]([O:25][CH3:26])[CH:17]=2)[C:22]([C:23]#[N:24])=[C:14]1[C:11]1[CH:12]=[CH:13][C:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])=[CH:9][CH:10]=1)[CH3:28]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 594254191-(2-chloroethyl)-3-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-urea

Produkt 1

HCID 594254061-ethyl-6-methoxy-2-[4-(2-oxo-imidazolidin-1-yl)-phenyl]-1H-indole-3-carbonitrileAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
49 °C

Versuchsvorschrift

To a solution of 1-(2-chloroethyl)-3-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-urea (100 mg, 0.252 mmol) in MeOH (10 mL) was added aqueous 1M KOH (504 uL) and then stirred at 49° C. for 24 h. The solvents were removed under reduced pressure. The residue was diluted with ethyl acetate and then washed with water. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was diluted with ethyl acetate and then triturated with hexane and the precipitate collected by filtration and washed well with 50% ethyl acetate in hexane and dried in vacuo to afford 1-ethyl-6-methoxy-2-[4-(2-oxo-imidazolidin-1-yl)-phenyl]-1H-indole-3-carbonitrile (56 mg, 62%).

Aufarbeitung

  1. customThe solvents were removed under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was diluted with ethyl acetate
  8. customtriturated with hexane
  9. filtrationthe precipitate collected by filtration
  10. washwashed well with 50% ethyl acetate in hexane
  11. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2d4b369f37504aa7966404818ccf001b
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013006B2

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