反应 #164698

反应方程式

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

收率 16.0%

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

收率 16.0%

溶剂

DMF

反应条件

后处理

1. 1
   其他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
   洗涤eluting with 0% to 100% acetonitrile in water
3. 3
   其他Drying under vacuum

实验过程

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).

来源