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

HRID 18031

Reaktionsgleichung

Reaktionsgleichung von HRID 18031
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12]([C:16](N(C)C)=[O:17])=[N:11][C:10]([OH:21])=[C:9]([OH:22])[C:8]=2[C:7]1=[O:23].[CH3:28][O-:29].[Mg+2].C[O-].[CH2:33](Br)[CH:34]=[CH2:35].Cl>CO.CS(C)=O>[CH2:33]([N:11]1[C:10](=[O:21])[C:9]([OH:22])=[C:8]2[C:13]([CH2:14][CH2:15][N:6]([CH2:5][C:4]3[CH:24]=[CH:25][C:26]([F:27])=[C:2]([Cl:1])[CH:3]=3)[C:7]2=[O:23])=[C:12]1[C:16]([O:29][CH3:28])=[O:17])[CH:34]=[CH2:35]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 164537Methanol, magnesium salt (2:1)HCID 178484497HCID 178484497, Verbindung

Produkt 1

HCID 66997076Methyl 2-(allyl)-6-(3-chloro-4-fluorobenzyl)-4-hydroxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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 (3.99 g, 10.511 mmol; Example 1, step 9) and magnesium methoxide in methanol (52.4 mL, 6-10% methanol solution available from Aldrich) in DMSO (100 mL) was heated at 60° C. for 30 minutes. Methanol was exhaustively removed under vacuum over 45 minutes. The residual DMSO solution was treated with allyl bromide (3.810 g, 31.52 mmol) and stirred at room temperature under an atmosphere of nitrogen for overnight. The reaction mixture was treated dilute hydrochloric acid. The solid precipitated was filtered to provide the title compound. (ES MS M+1=421.2)

Aufarbeitung

  1. customMethanol was exhaustively removed under vacuum over 45 minutes
  2. customThe solid precipitated
  3. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-d5b0488fcdf640e285853e30f7b3e33f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741315B2

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