4-Fluorophenyl isocyanate → N1-[5-({7-[3-(Dimethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thienyl]-N'-(4-fluorophenyl)urea

HRID 387853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387853
[CH2:1]([N:3]([CH2:27]C)[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([S:18][C:19]3[S:23][C:22]([NH2:24])=[CH:21][CH:20]=3)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:25][CH3:26])C.[F:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1>O1CCCC1>[CH3:27][N:3]([CH3:1])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([S:18][C:19]3[S:23][C:22]([NH:24][C:37]([NH:36][C:33]4[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=4)=[O:38])=[CH:21][CH:20]=3)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:25][CH3:26]

Komponenten

4

Edukt 2

HCID 709554-Fluorophenyl isocyanateHCID 589308085-({7-[3-(Diethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thiopheneamine

Produkt 1

HCID 67202083N1-[5-({7-[3-(Dimethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thienyl]-N'-(4-fluorophenyl)ureaAusbeute 6,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-({7-[3-(Diethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thiophenylamine (190 mg), parafluorophenyl isocyanate (69 mg) and tetrahydrofuran (30 ml) were stirred together at room temperature for 30 minutes. The organic solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (ethyl acetate, followed by ethyl acetate:methanol=10:1) using NH type silica gel. The solvent was distilled off under reduced pressure, and ethyl acetate was added to the residue for solidification to obtain 16 mg of a yellowish-brown solid.

Aufarbeitung

  1. distillationThe organic solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography (ethyl acetate, followed by ethyl acetate:methanol=10:1)
  3. distillationThe solvent was distilled off under reduced pressure, and ethyl acetate
  4. additionwas added to the residue for solidification

Quellen und Nachweise

ORD-Eintrag
ord-37967c42f7a34e688b8c9150ac24bbb8
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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