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

HRID 381351ノート

反応式

HRID 381351 の反応式
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]

参加物

6

反応物 4

HCID 700EthanolamineHCID 8471Triethylamine2 回HCID 62493Pivaloyl chlorideHCID 183628186-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6a51cee20714497890fd21e6b89cb137
出典データセット
uspto-grants-2001_10
特許番号
US06306860B1

反応ノート

読み込み中…