Potassium Carbonate → 3-(5-amino-2-methylphenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one

HRID 424703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424703
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[C:4]([NH:10][CH3:11])[CH:3]=1.C[O:13][C:14](=O)[CH2:15][C:16]1[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:17]=1[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:22][C:20]1[CH:19]=[CH:18][C:17]([CH3:23])=[C:16]([C:15]2[C:14](=[O:13])[N:10]([CH3:11])[C:4]3[C:5]([CH:8]=2)=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=3)[CH:21]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 234345716-Chloro-4-(methylamino)nicotinaldehydeHCID 46741401Methyl (5-amino-2-methylphenyl)acetate

Produkt 1

HCID 598338283-(5-amino-2-methylphenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

6-Chloro-4-methylamino-pyridine-3-carbaldehyde 6 (19.8 g, 116 mmol) is mixed with 2-(5-amino-2-methyl-phenyl)acetic acid methyl ester 7 (27 g, 151 mmol) and potassium carbonate (48.1 g, 348 mmol) in DMF (1 L). The mixture is heated to 100° C. for 16 h. After cooling to rt and removing solvent in vacuo, the crude product is purified using flash chromatography (ethyl acetate:petroleum ether=1:1). The title compound 8 is obtained as a pale solid. 1H NMR (300 MHz, CDCl3) δ 8.56 (s, 1H), 7.63 (s, 1H), 7.27 (s, 1H), 7.06 (d, J=8.1 Hz, 1H), 6.74 (dd, J=2.4, 8.1 Hz, 1H), 6.58 (d, J=2.4 Hz, 1H), 3.71 (s, 2H), 2.10 (s, 3H).

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. customremoving solvent in vacuo
  3. customthe crude product is purified

Quellen und Nachweise

ORD-Eintrag
ord-232758e3b0e74e7ab136d74a52e3065d
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106068B2

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