Phenethylamine → 2-Aminocarbonylamino-6-(2-phenylethylaminocarbonyl)indole-3-carboxamide

HRID 216640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216640
C(N(CC)C(C)C)(C)C.[CH:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH2:18])=[CH:12][CH:11]=1.[NH2:19][C:20]([NH:22][C:23]1[NH:24][C:25]2[C:30]([C:31]=1[C:32](=[O:34])[NH2:33])=[CH:29][CH:28]=[C:27]([C:35]([OH:37])=O)[CH:26]=2)=[O:21]>CN(C)C=O>[NH2:19][C:20]([NH:22][C:23]1[NH:24][C:25]2[C:30]([C:31]=1[C:32]([NH2:33])=[O:34])=[CH:29][CH:28]=[C:27]([C:35]([NH:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1)=[O:37])[CH:26]=2)=[O:21]

Komponenten

5

Edukt 3

HCID 1001PhenethylamineHCID 81531DiisopropylethylamineHCID 591898752-Aminocarbonylamino-3-carbamoylindole-6-carboxylic acid2×

Produkt 1

HCID 591897852-Aminocarbonylamino-6-(2-phenylethylaminocarbonyl)indole-3-carboxamideAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N,N-Diisopropylethylamine (0.20 mL, 1.14 mmol) and 2-phenethylamine (48 μL, 0.38 mmol) were added to a solution of 2-aminocarbonylamino-3-carbamoylindole-6-carboxylic acid (Compound 18-1, 0.10 g, 0.38 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N-tetramethyluronium hexafluorophosphate g, 0.38 mmol) in anhydrous N,N-dimethylformamide (4 mL), and the mixture was stirred at room temperature for 2.5 hours. After the reaction mixture was concentrated under reduced pressure, the precipitated solid was washed with saturated sodium hydrogen carbonate aqueous solution (20 mL), water (20 mL), and dried under reduced pressure to give the title compound (0.11 g) as a slightly yellow solid (yield 77%).

Aufarbeitung

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. washthe precipitated solid was washed with saturated sodium hydrogen carbonate aqueous solution (20 mL), water (20 mL)
  3. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a98e8728cda940329ed17534d7503369
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193237B2

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