3-Ethylphenyl isocyanate → 2-[3-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

HRID 530431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530431
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([C:17]([NH2:19])=[O:18])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]=[CH:6][CH:7]=1.[CH2:20]([C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1)[CH3:21]>C1COCC1.C(OCC)(=O)C>[CH2:20]([C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[N:9]([C:17]([NH2:19])=[O:18])[C:10]4[C:15]([CH:16]=3)=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:5]=[CH:6][CH:7]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)[CH3:21]

Komponenten

5

Edukt 2

HCID 27696373-Ethylphenyl isocyanateHCID 1212546152-(3-aminophenyl)-1H-indole-1-carboxamide

Produkt 1

HCID 1212546262-[3-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To the solution of 2-(3-aminophenyl)-1H-indole-1-carboxamide (50.2 mg, 0.2 mmol, 1 eq) in anhydrous THF (2 mL) was added 3-ethylphenyl isocyanate (29 μL, 1 eq) and the reaction solution was stirred at room temperature for one hour. It was then diluted with ethyl acetate, washed with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated and the oily residue was subject to a gradient column chromatography (from EtOAc-Hex 1:2 to MeOH-EtOAc 1:10). The product fractions were collected, concentrated, and the solid residue was triturated with EtOAc-Hex (1:1) to give 2-[3-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide as white solid upon filtration in amount of 32 mg.

Aufarbeitung

  1. washwashed with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine
  2. dry with materiallastly dried with anhydrous sodium sulfate
  3. customThe upper solution was decanted
  4. concentrationconcentrated
  5. customThe product fractions were collected
  6. concentrationconcentrated
  7. customthe solid residue was triturated with EtOAc-Hex (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-5fd432edaded4b82a89f52db1b06c390
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353093B2

Notizen zur Reaktion

Wird geladen…