Methyl iodide → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodide

HRID 469503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469503
[I:1][CH3:2].[CH3:3][O:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]([NH:23][C:24]2[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=2)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:12](=[O:22])[O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[CH:7][CH:6]=1>CCOC(C)=O>[I-:1].[CH2:30]([O:29][C:27]([C:26]1[CH:25]=[C:24]([NH:23][CH:11]([C:8]2[CH:9]=[N:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[C:12]([O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N+:16]([CH3:2])([CH2:17][CH2:18]3)[CH2:15]2)=[O:22])[CH:34]=[CH:33][CH:32]=1)=[O:28])[CH3:31]

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

Produkt 1

HCID 67124884(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Iodomethane (7.1 μl, 0.11 mmol) was added to a solution of ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (C65) (50 mg, 0.11 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was triturated with Et2O, filtered and dried. The product was purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodide (24.3 mg, 36.7% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried
  5. customThe product was purified by preparative HPLC (Eluent: CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-411c0350a18547b3a153d38184e4c314
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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