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

HRID 21578ノート

反応式

HRID 21578 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 102208805-Methoxy-1-methyl-3-(1-methylethoxy)-1H-indole-2-carboxamide収率 53.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-42b62a9fafc944d5b7d487f349339f77
出典データセット
uspto-grants-1995_06
特許番号
US05424329

反応ノート

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