2-Pyrazinecarboxylic acid → 1,6-Dihydro-6-oxo-1-[2-(2-pyrazinylcarbonylamino)ethyl]-3-pyridinecarboxylic acid methyl ester

HRID 2379086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2379086
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][NH2:14])[CH:6]=1)=[O:4].[N:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21](O)=[O:22].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl.CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][NH:14][C:21]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][N:15]=2)=[O:22])[CH:6]=1)=[O:4]

Komponenten

7

Edukt 4

HCID 10472-Pyrazinecarboxylic acidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 54083902Methyl 1-(2-aminoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Produkt 1

HCID 539914951,6-Dihydro-6-oxo-1-[2-(2-pyrazinylcarbonylamino)ethyl]-3-pyridinecarboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(2-aminoethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester (0.396 g, 2.02 mmol) was coupled with 2-pyrazinecarboxylic acid (0.251 g, 2.02 mmol) in a mixture of dichloromethane (34 ml) and dimethylformamide (35 ml) with triethylamine (1.41 ml, 10.1 mmol)and propylphosphonic acid anhydride (0.7 ml, added as a 0.7 ml ethyl acetate solution). After 18 hours, the mixture was concentrated and the residue slurried in dichloromethane and aqueous sodium bicarbonate. The layers were separated and the aqueous layer extracted with dichloromethane (2X) and the combined organic layers dried (Na2SO4). Filtration, concentration, and purification via medium pressure liquid chromotography (silica gel, 5% methanol/dichloromethane) gave the desired product, MP: 195°-197° C.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane (2X)
  4. dry with materialthe combined organic layers dried (Na2SO4)
  5. filtrationFiltration, concentration, and purification via medium pressure liquid chromotography (silica gel, 5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-811c07d4f77649279aa6a96f39177b3e
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05360808

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