Dicyclohexylcarbodiimide → 2-[1-(3-amino-2-pyridyl)piperazin-4-yl-carbonyl]-5-[N-(tetrahydro-2-furanon-3-yl)carbamoyl]pyridine

HRID 381379

反応式

HRID 381379 の反応式
[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.Br.[NH2:51][CH:52]1[CH2:57][CH2:56][O:55][C:53]1=[O:54]>C(Cl)Cl.C(N(CC)CC)C.O1CCCC1>[NH2:1][C:2]1[C:3]([N:8]2[CH2:9][CH2:10][N:11]([C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20](=[O:21])[NH:51][CH:52]4[CH2:57][CH2:56][O:55][C:53]4=[O:54])=[CH:18][N:17]=3)=[O:15])[CH2:12][CH2:13]2)=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 73508Homoserine lactone hydrobromideHCID 757711-HydroxybenzotriazoleHCID 18362790HCID 18362790、化合物

生成物 1

HCID 99533622-[1-(3-amino-2-pyridyl)piperazin-4-yl-carbonyl]-5-[N-(tetrahydro-2-furanon-3-yl)carbamoyl]pyridine収率 71%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

6-[1-(3-amino-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid (1 g) was added to a co-solvent of tetrahydrofuran (25 ml) and methylene chloride (15 ml) and with the successive addition of 1.3-dicyclohexylcarbodimide (1.3 g) and 1-hydroxybenzotriazole (0.46 g) at 15° C.˜20° C., the mixture was stirred for 2 hours. A mixture of α-amino-γ-butyrolactone hydrobromide (1.1 g) and triethylamine (0.9 ml) was added again to the mixture at 20° C. and stirred at 20° C.˜25° C. for 3 hours. With the addition of methylene chloride (50 ml), the mixture was washed with water 3 times, dried over magnesium sulfate and concentrated under reduced pressure. The concentrated residue was treated with ether for crystallization and recrystallized with chloroform and tetrahydrofuran to give a desired compound of 1.07 g (yield: 71%).

後処理

  1. additionwas added again to the mixture at 20° C.
  2. stirringstirred at 20° C.˜25° C. for 3 hours
  3. washthe mixture was washed with water 3 times
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe concentrated residue was treated with ether for crystallization
  7. customrecrystallized with chloroform and tetrahydrofuran

出典と根拠

ORDレコード
ord-9401c1e6406940749ec725ff5f3c46de
出典データセット
uspto-grants-2001_10
特許番号
US06306860B1

関連ノート

読み込み中…