Potassium Carbonate → HCID 9815137, Verbindung

HRID 1355368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1355368
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[C:9]([C:18]#[N:19])=[N:10][CH:11]=[C:12]([NH:14][CH2:15][CH2:16][OH:17])[N:13]=1.Cl.[CH2:21]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][CH2:24][NH:23][CH2:22]1>CN(C)C=O>[OH:17][CH2:16][CH2:15][NH:14][C:12]1[N:13]=[C:8]([N:23]2[CH2:22][CH2:21][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[CH2:25][CH2:24]2)[C:9]([C:18]#[N:19])=[N:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 170652302,3,4,5-Tetrahydro-1H-3-benzazepine--hydrogen chloride (1/1)HCID 187532053-Bromo-5-[(2-hydroxyethyl)amino]-2-pyrazinecarbonitrile

Produkt 1

HCID 9815137HCID 9815137, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

0.415 g (3.00 mmol) of potassium carbonate were added slowly at room temperature to a solution of 0.243 g (1.0 mmol) of the 3-bromo-5-(2-hydroxy-ethylamino)-pyrazine-2-carbonitrile and 0.220 g (1.2 mmol) of the 2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride (J. Heterocycl. Chem. 1971, 8(5), 779-83) in 10.0 ml of N,N-dimethyl-formamide. The reaction mixture was stirred at room temperature for 64 hours and at 80° C. for 5 hours. It was subsequently poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 9:1 to 0:10 v/v gradient of hexane and ethylacetate as the eluent giving 0.308 g (1.0 mmol, 100% of theory) of the 5-(2-hydroxy-ethylamino)-3-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-pyrazine-2-carbonitrile as light yellow amorphous solid; MS: 310 (M+H)+.

Aufarbeitung

  1. extractionextracted 3 times with 50 ml of dichloromethane
  2. dry with materialThe combined dichloromethane phases were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue formed
  5. customwas chromatographed on silica gel with a 9:1 to 0:10 v/v gradient of hexane and ethylacetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-365ede64f4e147688d4caef3b54cecb4
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586422B2

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