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Ethanolamine → 6-[4-(3-amino-2-pyridyl)piperazine-1-carbonyl]-N-(2-hydroxyethyl)pyridine-3-carboxamide

HRID 381362
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HRID 381362 반응식
[NH2:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=3)=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[CH2:50]([CH2:52][NH2:53])[OH:51]>C(Cl)Cl.O1CCCC1>[NH2:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20](=[O:21])[NH:53][CH2:52][CH2:50][OH:51])=[CH:18][N:17]=3)=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 700EthanolamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 183627906-[1-(3-Amino-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid

생성물 1

HCID 4997296-[4-(3-amino-2-pyridyl)piperazine-1-carbonyl]-N-(2-hydroxyethyl)pyridine-3-carboxamide수율 78%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
2회
HCID 8028Tetrahydrofuran용매

실험 절차

6-[1-(3-Amino-2-pyridyl)piperazine-4-yl-carbonyl]nicotinic acid (0.5 g) was added to a co-solvent of tetrahydrofuran (10 ml) and methylene chloride (10 ml) and with the successive addition of 1,3-dicyclohexylcarbodimide (0.65 g) and 1-hydroxybenzotriazole (0.23 g) at 15˜20° C., the mixture was stirred for 2 hours. With the addition of ethanolamine (0.18 ml), the mixture was stirred again at 20˜25° C. for 2 hours. Methylene chloride (30 ml) was added again to the mixture, washed with water 3 times, dried over magnesium sulfate and concentrated under reduced pressure. The concentrated residue was treated with ether for crystallization. The solid was recrystallized with ethanol and hexane to give a desired compound of 0.44 g (yield: 78%).

후처리

  1. stirringthe mixture was stirred again at 20˜25° C. for 2 hours
  2. washwashed with water 3 times
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionThe concentrated residue was treated with ether for crystallization
  6. customThe solid was recrystallized with ethanol and hexane

출처 및 근거

ORD 기록
ord-231f87ab9010466d802dbba06279a088
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06306860B1

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