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

HRID 2379084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2379084
[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].[CH3:15][C:16]1[N:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl.C(OCC)(=O)C>[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:22]([C:19]2[CH:20]=[N:21][C:16]([CH3:15])=[CH:17][CH:18]=2)=[O:23])[CH:6]=1)=[O:4]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 1378606-Methylnicotinic acidHCID 516892Sodium BicarbonateHCID 54083902Methyl 1-(2-aminoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Produkt 1

HCID 540152651,6-Dihydro-1-[2-(6-methyl-3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(2-aminoethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester (0.50 g, 2.55 mmol) was coupled with 6-methyl-3-pyridinecarboxylic acid (0.42 g, 3.1 mmol)in dimethylformamide (42.5 ml) with triethylamine (1.80 ml, 12.75 mmol) and propylphosphonic acid anhydride (0.90 ml, added as a 0.90 ml ethyl acetate solution). After 72 hours, dichloromethane and aqueous sodium bicarbonate were added. The layers were separated and the organic layer washed with brine and dried (Na2SO4). Filtration, concentration, and purification by medium pressure liquid chromotography (silica gel, 4-6% methanol/dichloromethane) gave the desired product, MP: 184°-185° C.

Aufarbeitung

  1. customThe layers were separated
  2. washthe organic layer washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationFiltration, concentration, and purification by medium pressure liquid chromotography (silica gel, 4-6% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-3008e11dfab04710b74644317a63ab06
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05360808

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