2-Methoxyethylamine → 6-(2-Methoxyethylcarbamoyl)-7-methoxy-4-(indol-5-yloxy) quinoline

HRID 387974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387974
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[C:7]2[O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)([OH:3])=O.[CH3:26][O:27][CH2:28][CH2:29][NH2:30].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.O>[CH3:26][O:27][CH2:28][CH2:29][NH:30][C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][CH:8]=[C:7]2[O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)=[O:3]

Komponenten

8

Edukt 4

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 229369786-Carboxy-7-methoxy-4-(indol-5-yloxy)quinoline

Produkt 1

HCID 229365306-(2-Methoxyethylcarbamoyl)-7-methoxy-4-(indol-5-yloxy) quinoline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

After dissolving 6-carboxy-7-methoxy-4-(indol-5-yloxy)quinoline (100 mg) in dimethylformamide (4.0 ml), there were added methoxyethylamine (0.04 ml), triethylamine (0.08 ml) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (198 mg), and the mixture was stirred at room temperature for 5 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and then the organic layer was washed with water and saturated saline in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Ethyl acetate was used for recrystallization to obtain the title compound (86 mg).

Aufarbeitung

  1. washthe organic layer was washed with water and saturated saline in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customEthyl acetate was used for recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-36b991935a7d4913a6b2f0235f64705c
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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