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

HRID 413304노트

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HRID 413304 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
65 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b69e4e60b68648bf9532f1e2bd147744
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566377B2

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