Ethoxyethylamine → N1-Ethyl-5-(2-(((2-ethoxyethyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide

HRID 2215508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215508
[CH2:1]([NH:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23](=[O:31])OC4C=CC=CC=4)[CH:17]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=[O:5])[CH3:2].[CH2:32]([O:34][CH2:35][CH2:36][NH2:37])[CH3:33]>CN(C)C=O>[CH2:1]([NH:3][C:4]([N:6]1[C:14]2[C:13](=[CH:12][C:11]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]([NH:37][CH2:36][CH2:35][O:34][CH2:32][CH3:33])=[O:31])[CH:17]=3)=[CH:10][CH:9]=2)[CH:8]=[CH:7]1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 66970EthoxyethylamineHCID 21949099Phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate

Produkt 1

HCID 10454295N1-Ethyl-5-(2-(((2-ethoxyethyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate (100 mg, 0.24 mmol) was dissolved in N,N-dimethylformamide (1.0 ml), and 2-ethoxyethylamine (0.063 ml, 0.6 mmol) was added while stirred at room temperature. After 1 hour, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the crystals were precipitated from ethyl acetate-hexane (1:5), filtered off, and dried under aeration to yield the title compound (100 mg, 0.24 mmol, quantitative) as white crystals.

Aufarbeitung

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe crystals were precipitated from ethyl acetate-hexane (1:5)
  6. filtrationfiltered off
  7. customdried under aeration

Quellen und Nachweise

ORD-Eintrag
ord-37a4786540554f72a277addd115d9462
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109219B2

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