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

HRID 381379

Reaktionsgleichung

Reaktionsgleichung von HRID 381379
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9401c1e6406940749ec725ff5f3c46de
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306860B1

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