Reaktion #164698

Reaktionsgleichung

N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-N′-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidine

Intermediate 4

N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-N′-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidine

benzyl bromoacetate

→

title compound

Ausbeute 16.0%

1-Carboxymethyl-3-[N′-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidino]-1-azoniabicyclo[2.2.2]octane bromide

Ausbeute 16.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient) and further on a PoraPak Rxn RP cartridge (Waters, 6 mL)
2. 2
   Wascheneluting with 0% to 100% acetonitrile in water
3. 3
   SonstigeDrying under vacuum

Vorschrift

N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-N′-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidine (Intermediate 4, 152 mg, content ca. 66%, 0.30 mmol) and benzyl bromoacetate (Aldrich, 0.052 mL, 0.33 mmol) are treated with DMF (1 mL) and the mixture stirred at r.t. for ca. 18 h. The crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient) and further on a PoraPak Rxn RP cartridge (Waters, 6 mL), eluting with 0% to 100% acetonitrile in water. Drying under vacuum yields the title compound (23 mg).

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