反応 #164698

反応方程式

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

収率 16.0%

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

収率 16.0%

溶媒

DMF

反応条件

後処理

1. 1
   その他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)
2. 2
   洗浄eluting with 0% to 100% acetonitrile in water
3. 3
   その他Drying under vacuum

実験手順

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).

出典