Diisopropylethylamine → 5-[[2-(dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

HRID 897302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 897302
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:24][N:25]([CH3:31])[C:26](=[O:30])[CH2:27][NH:28][CH3:29].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:24][N:25]([CH3:31])[C:26](=[O:30])[CH2:27][N:28]([CH3:29])[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2063713N,N-dimethyl-2-(methylamino)acetamideHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Produkt 1

HCID 159582765-[[2-(dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

Into a 10 mL pressure vessel equipped with a magnetic stir bar was placed 0.1 g (0.266 mmol) 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (see Example 126), 0.031 g (0.27 mmol) N,N-dimethyl-2-(methylamino)acetamide, 0.726 mL (0.8 mmol) N,N-diisopropylethylamine and 5 mL DMF. The vessel was sealed and heated on an oil bath to 135° C. for 18 hrs., after which the mixture was cooled and the solvent removed in vacuo. The residue was purified by reverse phase HPLC on a C18 column using acetonitrile/water as eluent to give 5-[[2-(dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide.

Aufarbeitung

  1. customInto a 10 mL pressure vessel equipped with a magnetic stir bar
  2. customThe vessel was sealed
  3. temperature, after which the mixture was cooled
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by reverse phase HPLC on a C18 column

Quellen und Nachweise

ORD-Eintrag
ord-f650dd53b06a455094f07ddcb819e93b
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921759B2

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