Water → 5-Methoxy-1-methyl-3-(1-methylethoxy)-1H-indole-2-carboxamide

HRID 21578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21578
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([C:13](O)=[O:14])=[C:6]2[O:16][CH:17]([CH3:19])[CH3:18].C(N1C=CN=C1)([N:22]1C=CN=C1)=O.[OH-].[NH4+].O>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7]([C:13]([NH2:22])=[O:14])=[C:6]2[O:16][CH:17]([CH3:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 138857995-Methoxy--methyl-3-(1-methylethoxy)-1H-indole-2-carboxylic acid

Produkt 1

HCID 102208805-Methoxy-1-methyl-3-(1-methylethoxy)-1H-indole-2-carboxamideAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 5-methoxy-1-methyl-3-(1-methylethoxy)-1H-indole-2-carboxylic acid (4.0 g, 15 mmol; Unangst PC, et al., J. Med. Chem. 1989;32:1360) and 1,1'-carbonyldiimidazole (2.6 g, 16 mmol) in 75 mL of acetonitrile is stirred at reflux for 2 hours. The mixture is cooled slightly and 75 mL of concentrated ammonium hydroxide is added. After stirring for 15 minutes, the mixture is added to 600 g of ice and water. The precipitated solid is filtered, washed with water, and recrystallized from aqueous acetonitrile to give 2.1 g (53%) of product; mp 147°-149° C.

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture is cooled slightly
  3. stirringAfter stirring for 15 minutes
  4. filtrationThe precipitated solid is filtered
  5. washwashed with water
  6. customrecrystallized from aqueous acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-42b62a9fafc944d5b7d487f349339f77
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424329

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