Dimethylformamide → 2-Methoxyethyl 4-(4-(((4-fluoroanilino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylate

HRID 1433548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433548
[F:1][C:2]1[CH:33]=[CH:32][C:5]([NH:6][C:7]([NH:9][C:10]2[CH:31]=[CH:30][C:13]([O:14][C:15]3[C:24]4[C:19](=[CH:20][C:21]([O:28][CH3:29])=[C:22]([C:25]([OH:27])=[O:26])[CH:23]=4)[N:18]=[CH:17][CH:16]=3)=[CH:12][CH:11]=2)=[O:8])=[CH:4][CH:3]=1.Cl.C(N=C=NC[CH2:41][CH2:42]N(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.CN(C)[CH:66]=[O:67]>C(OCC)(=O)C.COCCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][C:7]([NH:9][C:10]2[CH:31]=[CH:30][C:13]([O:14][C:15]3[C:24]4[C:19](=[CH:20][C:21]([O:28][CH3:29])=[C:22]([C:25]([O:27][CH2:41][CH2:42][O:67][CH3:66])=[O:26])[CH:23]=4)[N:18]=[CH:17][CH:16]=3)=[CH:12][CH:11]=2)=[O:8])=[CH:32][CH:33]=1

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 229363504-(4-(((4-Fluoroanilino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylic acid

Produkt 1

HCID 230695712-Methoxyethyl 4-(4-(((4-fluoroanilino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylateAusbeute 49,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80192-MethoxyethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After dissolving 4-(4-(((4-fluoroanilino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylic acid (84 mg, 0.19 mmol) in dimethylformamide (1 ml), there were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (54 mg, 0.28 mmol), 1-hydroxy-1H-benzotriazole monohydrate (38 mg, 0.28 mmol), triethylamine (0.079 ml, 0.56 mmol) and 2-methoxyethanol (0.15 ml) while stirring on ice, and the mixture was stirred overnight at room temperature. The reaction solution was directly subjected to silica gel column chromatography (eluent—ethyl acetate), the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, and the crystals were filtered out and blow-dried to obtain the title compound (47.1 mg, 0.093 mmol, 49.6%) as white crystals.

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. additionthe fraction containing the target substance
  3. concentrationwas concentrated
  4. additiondiluted with hexane
  5. filtrationthe crystals were filtered out and
  6. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-04db75d4bd5040e89e2214750796fb8a
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612092B2

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