1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethoxy-benzoyl)-1H-[1,8]naphthyridin-4-one

HRID 227133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227133
CON(C)[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=2)[CH:7]=1)=[O:5].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([Mg]Br)[CH:31]=[CH:32][C:33]=1[O:34][CH3:35]>C1COCC1>[Br:24][C:20]1[N:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][N:10]=3)[C:15](=[O:16])[C:6]([C:4](=[O:5])[C:31]3[CH:30]=[CH:29][C:28]([O:27][CH3:26])=[C:33]([O:34][CH3:35])[CH:32]=3)=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 577545871-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amideHCID 178491916HCID 178491916, Verbindung

Produkt 1

HCID 577546341-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethoxy-benzoyl)-1H-[1,8]naphthyridin-4-oneAusbeute 18,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Experimental conditions analogous to those described for Step 6 of Example 60, from 100 mg (0.248 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide in THF 2 ml, was added 1.09 ml (0.545 mmol) 3,4-dimethoxyphenylmagnesium bromide. The reaction mixture was stirred at room temperature for 30 min, then quenched with saturated solution of NH4Cl, extracted with ethyl acetate and purified with flash chromatography to give the desired product 22 mg. LCMS observed for (M+H)+: 480.

Aufarbeitung

  1. customquenched with saturated solution of NH4Cl
  2. extractionextracted with ethyl acetate
  3. custompurified with flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ff776be363784da2a99a419d704eaf53
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557213B2

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