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

HRID 381351노트

반응식

HRID 381351 반응식
C(N(CC)CC)C.[CH:8]([NH:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][N:27]=3)=[O:25])[CH2:20][CH2:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1)([CH3:10])[CH3:9].C(Cl)(=O)C(C)(C)C.[CH2:42]([CH2:44][NH2:45])[OH:43]>C(Cl)Cl>[OH:43][CH2:42][CH2:44][NH:45][C:30]([C:29]1[CH:33]=[CH:34][C:26]([C:24]([N:21]2[CH2:22][CH2:23][N:18]([C:13]3[C:12]([NH:11][CH:8]([CH3:9])[CH3:10])=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:19][CH2:20]2)=[O:25])=[N:27][CH:28]=1)=[O:31]

참가 물질

6

반응물 4

HCID 700EthanolamineHCID 8471Triethylamine2회HCID 62493Pivaloyl chlorideHCID 183628186-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid

생성물 1

HCID 499739N-(2-hydroxyethyl)-6-[4-[3-(isopropylamino)-2-pyridyl]piperazine-1-carbonyl]pyridine-3-carboxamide수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
5 °C

실험 절차

Triethylamine (0.54 ml) was added to 6-[1-[3-(isopropylamino)-2-pyridyl]piperazine-4-yl-carbonyl]nicotinic acid (1.3 g) in methylene chloride (40 ml) for dissolution and cooled. With the slow addition of pivaloyl chloride (0.45 ml) at 0° C.˜5° C., the reaction mixture was stirred at 5° C. for 2 hours. With the addition of triethylamine (0.6 ml) and ethanolamine (0.25 ml), the mixture was stirred at 5° C.˜10° C. for 3 hours. The solution was washed with aqueous sodium bicarbonate and water twice. The separated organic layer was concentrated under reduced pressure. The concentrated residue was treated with ether for crystallization and recrystallized with ethanol and isopropyl ether to give a desired compound of 1.2 g (yield: 83%).

후처리

  1. temperaturecooled
  2. stirringthe mixture was stirred at 5° C.˜10° C. for 3 hours
  3. washThe solution was washed with aqueous sodium bicarbonate and water twice
  4. concentrationThe separated organic layer was concentrated under reduced pressure
  5. additionThe concentrated residue was treated with ether for crystallization
  6. customrecrystallized with ethanol and isopropyl ether

출처 및 근거

ORD 기록
ord-6a51cee20714497890fd21e6b89cb137
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306860B1

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