Citric Acid → 4-(1-methyl-1H-pyrrol-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid

HRID 454762ノート

反応式

HRID 454762 の反応式
CO.[OH-].[Na+].[CH3:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[C:13]([NH:24][C:25]([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:32]=2)=[O:26])[CH:12]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[CH3:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[CH:23]=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:24][C:25]([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:32]=2)=[O:26])[CH:12]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58508465tert-butyl 4-(1-methyl-1H-pyrrol-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoate

生成物 1

HCID 585086014-(1-methyl-1H-pyrrol-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid収率 80.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
52.5 °C

実験手順

Methanol (1.5 mL), dioxane (1.5 mL), and a 2 mol/L aqueous solution of sodium hydroxide (0.24 mL) were added the obtained tert-butyl 4-(1-methyl-1H-pyrrol-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoate (71 mg), followed by stirring at 50 to 55° C. for 2 hours. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid was added thereto. The solid substance was collected by filtration to obtain 50 mg of 4-(1-methyl-1H-pyrrol-2-yl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a white solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid substance was collected by filtration

出典と根拠

ORDレコード
ord-66236804cad6403dae165f2f5e8a5155
出典データセット
uspto-grants-2013_07
特許番号
US08492582B2

反応ノート

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