Hydrochloric Acid → HCID 54692271, Verbindung

HRID 1817339

Reaktionsgleichung

Reaktionsgleichung von HRID 1817339
[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:18]([CH3:20])[CH3:19])=[O:17])=[N:11][C:10]([OH:21])=[C:9]([OH:22])[C:8]=2[C:7]1=[O:23].[CH3:28][O-].C[O-].[Mg+2].CI.Cl.S(=O)(O)[O-].[Na+]>CS(C)=O.CO.O>[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:8](=[C:9]([OH:22])[C:10](=[O:21])[N:11]([CH3:28])[C:12]=2[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:7]1=[O:23]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 164537Methanol, magnesium salt (2:1)HCID 23665763Sodium BisulfiteHCID 178484497HCID 178484497, Verbindung

Produkt 1

HCID 54692271HCID 54692271, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 6-(3-chloro-4-fluorobenzyl)-3,4-dihydroxy-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide (0.1 g, 0.254 mmol) in dry DMSO (5 mL) was added magnesium methylate (1.097 mL of a 6-10% methanol solution, 0.792 mmol), and the reaction was heated to 60° C. for 0.5 hour. The reaction mixture was rotavapped to remove all of the MeOH. The heat gun was used to drive all MeOH from the bump bulb. The reaction was treated with methyl iodide (0.079 mL, 6.35 mmol) and allowed to stir at 60° C. overnight. LCMS showed trace starting material remaining and mostly N-alklated product formed (O-alkylated products minor). The reaction was diluted with 0.5 mL MeOH then 1 N HCl was added until a precipitate began to form. A 5 mL portion of 10% sodium bisulfite was added and the brown mixture turned green. Water was added and the mixture stirred for 1 hr, then the mixture was partitioned with chloroform 20 mL and 1 N HCl 20 mL. The organic layer was washed 2 times more with 1 N HCl and then with brine, dried over Na2SO4, filtered and evaporated to an oil. The residue was passed through a Gilson reverse phase column eluting from 95:5 to 5:95 to give an oil after concentration.

Aufarbeitung

  1. customto remove all of the MeOH
  2. custommostly N-alklated product formed (O-alkylated products minor)
  3. customto form
  4. stirringthe mixture stirred for 1 hr
  5. customthe mixture was partitioned with chloroform 20 mL and 1 N HCl 20 mL
  6. washThe organic layer was washed 2 times more with 1 N HCl
  7. dry with materialwith brine, dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to an oil
  10. washeluting from 95:5 to 5:95
  11. customto give an oil
  12. concentrationafter concentration

Quellen und Nachweise

ORD-Eintrag
ord-2859d8b45ec7406898cead88d0a938eb
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598264B2

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