Methyl iodide → 4-[(1-methylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

HRID 1533754

Reaktionsgleichung

Reaktionsgleichung von HRID 1533754
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]([NH:12][C:13]3[CH:44]=[CH:43][C:16]([C:17]([N:19]([CH3:42])[C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=4[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([N:35]4[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]4)=[O:34])=[O:18])=[CH:15][C:14]=3[O:45][CH3:46])=[O:11])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:47]C(C)([O-])C.[K+].CI>CN(C)C=O>[CH3:47][N:1]1[C:9]2[C:4](=[C:5]([C:10]([NH:12][C:13]3[CH:44]=[CH:43][C:16]([C:17]([N:19]([CH3:42])[C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=4[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([N:35]4[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]4)=[O:34])=[O:18])=[CH:15][C:14]=3[O:45][CH3:46])=[O:11])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 183548224-[(indol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 183549294-[(1-methylindol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-[(indol-4-yl)carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (160 mg) in N,N-dimethylformamide (3.0 ml) was added portionwise potassium tert-butoxide (37.3 mg) at 0° C. and the mixture was stirred at 0° C. for 1 hour. Methyl iodide (47.2 mg) was added to the mixture and the solution was stirred at 0° C. for 1 hour. The reaction was quenched with water and then the aqueous solution was extracted with ethyl acetate. Drying, filtering and removal of solvents afforded a crude product. The crude product was purified by column chromatography (eluent; 2% methanol in chloroform) to give 4-[(1-methylindol-4-yl)-carbonyl]amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (65 mg) as a white syrup.

Aufarbeitung

  1. stirringthe solution was stirred at 0° C. for 1 hour
  2. customThe reaction was quenched with water
  3. extractionthe aqueous solution was extracted with ethyl acetate
  4. customDrying
  5. filtrationfiltering
  6. customremoval of solvents
  7. customafforded a crude product
  8. customThe crude product was purified by column chromatography (eluent; 2% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-a743f5831bd04840af832471622f8e20
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207693B1

Verknüpfte Notizen

Wird geladen…