3-Ethylphenyl isocyanate → 2-[4-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

HRID 530425

Reaktionsgleichung

Reaktionsgleichung von HRID 530425
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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:7]=[CH:6][C:5]([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:4][CH:3]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)[CH3:21]

Komponenten

5

Edukt 2

HCID 27696373-Ethylphenyl isocyanateHCID 1212546212-(4-Amino-phenyl)-indole-1-carboxylic acid amide

Produkt 1

HCID 1212546082-[4-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The reaction mixture of 2-(4-amino-phenyl)-indole-1-carboxylic acid amide (125.5 mg, 0.5 mmol, 1 eq) and 3-ethylphenyl isocyanate (0.073 mL, 1 eq) in anhydrous THF (4 mL) was stirred at room temperature for 2 hours. It was then diluted with ethyl acetate, washed sequentially with aqueous NH4Cl, saturated aqueous NaHCO3, brine, and dried with anhydrous sodium sulfate. The upper liquor was decanted, concentrated, and the solid residue was triturated with EtOAC-Hex (1:1). 2-[4-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide was obtained as white solid upon filtration in amount of 156 mg (78%).

Aufarbeitung

  1. washwashed sequentially with aqueous NH4Cl, saturated aqueous NaHCO3, brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe upper liquor was decanted
  4. concentrationconcentrated
  5. customthe solid residue was triturated with EtOAC-Hex (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-de42bfbb51354e47b5692def9fbaddc0
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353093B2

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