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

HRID 381379

반응식

HRID 381379 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.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

참가 물질

8

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 73508Homoserine lactone hydrobromideHCID 757711-HydroxybenzotriazoleHCID 18362790HCID 18362790, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9401c1e6406940749ec725ff5f3c46de
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306860B1

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