反応 #164699

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

3,4,5-trimethoxybenzyl chloride

→

title compound

収率 42.0%

3-[N′-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-guanidino]-1-(3,4,5-trimethoxybenzyl)-1-azoniabicyclo[2.2.2]octane chloride

収率 42.0%

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)
2. 2
   その他The product thus obtained
3. 3
   その他is triturated with a mixture of diethyl ether (4 mL) and methanol (1.5 mL)
4. 4
   ろ過collected by filtration
5. 5
   その他dried under vacuum at 70° C
6. 6
   ろ過Further trituration with water (0.3 mL), filtration
7. 7
   その他drying under vacuum at 70° C.

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 3,4,5-trimethoxybenzyl chloride (Aldrich, 77 mg, 0.36 mmol) is stirred in DMF (1 mL) at r.t. for ca. 18 h. The crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient). The product thus obtained is triturated with a mixture of diethyl ether (4 mL) and methanol (1.5 mL), collected by filtration and dried under vacuum at 70° C. Further trituration with water (0.3 mL), filtration and drying under vacuum at 70° C. yields the title compound (35 mg).

出典