Реакция #46270

Уравнение реакции

1-bromo-4-chlorobutane

6-(3-chloro-4-fluorobenzyl)-3,4-dihydroxy-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide

magnesium methoxide

→

title compound

Methyl 2-(4-chlorobutyl)-6-(3-chloro-4-fluorobenzyl)-4-hydroxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

Растворители

ethyl acetate

DMSO

methanol

DMSO

Условия реакции

Обработка

1. 1
   ДругоеMethanol was exhaustively removed under vacuum over 45 minutes
2. 2
   Промывкаwashed with dilute hydrochloric acid
3. 3
   ЭкстракцияThe organic extract
4. 4
   Промывкаwas washed with 10% aqueous potassium carbonate
5. 5
   Сушкаdried over anhydrous sodium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated under vacuum
8. 8
   ДругоеThe residue was triturated with diethyl ether
9. 9
   ДругоеThe solid precipitated
10. 10
    Фильтрацияwas collected by filtration

Методика

A mixture of 6-(3-chloro-4-fluorobenzyl)-3,4-dihydroxy-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide (0.80 g, 2.19 mmol) and magnesium methoxide in methanol (10.6 mL, 6-10% methanol solution available from Aldrich) in DMSO (22 mL) was heated at 60° C. for one hour. Methanol was exhaustively removed under vacuum over 45 minutes. The resulting DMSO solution was treated with 1-bromo-4-chlorobutane (1.80 g, 10.50 mmol) and stirred at 60° C. under an atmosphere of nitrogen for one hour. The reaction mixture was diluted with ethyl acetate and washed with dilute hydrochloric acid. The organic extract was washed with 10% aqueous potassium carbonate, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was triturated with diethyl ether. The solid precipitated was collected by filtration to provide the title compound. ES MS M+1=471

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