Water → HCID 66771690, Verbindung

HRID 241532

Reaktionsgleichung

Reaktionsgleichung von HRID 241532
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]([C:7]([OH:9])=O)[C:2]=1[C:10]([OH:12])=[O:11].[CH2:13]([NH2:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.O>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:13]([NH:25][C:7]([C:3]1[C:2]([C:10]([OH:12])=[O:11])=[N:1][CH:6]=[CH:5][N:4]=1)=[O:9])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

7

Edukt 4

HCID 962WaterHCID 13583DodecylamineHCID 666282,3-Pyrazinedicarboxylic acidHCID 2724699PyBOP

Produkt 1

HCID 66771690HCID 66771690, VerbindungAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Pyrazine-2,3-dicarboxylic acid (624 mg, 4.0 mmol), 1-dodecylamine (740 mg, 4.0 mmol), benzotriazole-1-yl-oxytripyrrolidinylphosphonium hexafluorophosphate (2.6 g, 4.8 mmol) and 4-dimethylaminopyridine (488 mg, 0.4 mmol) were dissolved in N,N-dimethylformamide (10 mL) and stirred at room temperature overnight. The reaction mixture was poured into water, then extracted three times with ethyl acetate. The isolated organic phase was dried with anhydrous Na2SO4. The solvent was removed by vaporizing under reduced pressure. The residue was purified by silica column chromatography (developing agent: dichloromethane/methanol=30/1) to produce 3-(dodecylcarbamoyl)pyrazine-2-carboxylic acid (650 mg).

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe isolated organic phase was dried with anhydrous Na2SO4
  3. customThe solvent was removed
  4. customThe residue was purified by silica column chromatography (developing agent: dichloromethane/methanol=30/1)

Quellen und Nachweise

ORD-Eintrag
ord-6e7de0eca3ab4b16acf516ca18312e5e
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653048B2

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