4-Methoxybenzylamine → 6-(4-methoxybenzyl)-3-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 533162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533162
[CH:1]([C:3]1[N:12]=[CH:11][C:10]([CH:13]=[CH2:14])=[CH:9][C:4]=1[C:5]([O:7]C)=O)=[CH2:2].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1>CC(N(C)C)=O>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:22]2[CH2:2][CH2:1][C:3]3[N:12]=[CH:11][C:10]([CH:13]=[CH2:14])=[CH:9][C:4]=3[C:5]2=[O:7])=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 754524-MethoxybenzylamineHCID 68008364HCID 68008364, Verbindung

Produkt 1

HCID 680082206-(4-methoxybenzyl)-3-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Methyl 2,5-divinylnicotinate (2.1 g, 11.1 mmol) was combined with p-methoxybenzylamine (2 mL, 15 mmol) and dimethylacetamide (7 mL) and heated for 20 min in a microwave reactor at 150° C. The reaction mixture was concentrated and purified over silica gel (0-100% EtOAc/hexanes) using automated chromatography. The product containing fractions were combined and evaporated under reduced pressure to give the compound (2.99 g, 92%). LC-MS (M+H)=295.1.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompurified over silica gel (0-100% EtOAc/hexanes)
  3. additionThe product containing fractions
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ae011d635ee54892ab279714c536943e
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853237B2

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