Ethanolamine → 6-[4-(2-aminoethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 413304ノート

反応式

HRID 413304 の反応式
[CH2:1]([CH2:3][NH2:4])[OH:2].CC(C)([O-])C.[K+].F[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:19][CH2:20][C:21](=[O:24])[NH:22][N:23]=2)=[CH:14][CH:13]=1.O>CS(C)=O>[NH2:4][CH2:3][CH2:1][O:2][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH2:19][CH2:20][C:21](=[O:24])[NH:22][N:23]=2)=[CH:16][CH:17]=1

参加物

6

反応物 4

HCID 700EthanolamineHCID 962WaterHCID 6058786-(4-Fluorophenyl)-4,5-dihydro-3(2H)-pyridazinoneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 144418666-[4-(2-aminoethoxy)-phenyl]-4,5-dihydro-3(2H)-pyridazinone収率 34.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
65 °C

実験手順

In a flame-dried, round-bottomed flask, ethanolamine (1.7 ml, 28.1 mmol) was dissolved in dimethylsulfoxide (9.5 ml), and potassium tert-butoxide (95%, 3.3 g, 28.1 mmol) was added to the solution. This mixture was stirred at about 65° C. for about ten minutes, and then 6-(4-fluorophenyl)-4,5-dihydro-2H-pyridazine-3-one (3.6 g, 18.7 mmol) was added. This dark-colored solution was heated to about 80° C. for about twelve hours, and was then cooled to room temperature. Water was added, and the resulting tan solid was removed by filtration. This crude solid was then purified by column chromatography (silica gel; 5% methanol/dichloromethane to 15% methanol/dichloromethane) to afford the product as a white solid (1.5 g, 34% yield). LRMS ([M+H]+)=234.2.

後処理

  1. temperatureThis dark-colored solution was heated to about 80° C. for about twelve hours
  2. temperaturewas then cooled to room temperature
  3. customthe resulting tan solid was removed by filtration
  4. customThis crude solid was then purified by column chromatography (silica gel; 5% methanol/dichloromethane to 15% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-b69e4e60b68648bf9532f1e2bd147744
出典データセット
uspto-grants-2003_05
特許番号
US06566377B2

反応ノート

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