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

HRID 502210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502210
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) is added aqueous 1M KOH (504 uL) and then stirred at 49° C. for 24 h. The solvents are removed under reduced pressure. The residue is diluted with ethyl acetate and then washed with water. The organic layer is dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue is 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 are removed under reduced pressure
  2. additionThe residue is diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer is dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue is 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-836c0a6a8fe741c1b9115bde673174a1
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772271B2

Notizen zur Reaktion

Wird geladen…