Reaktion #164699

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

3,4,5-trimethoxybenzyl chloride

→

title compound

Ausbeute 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

Ausbeute 42.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient)
2. 2
   SonstigeThe product thus obtained
3. 3
   Sonstigeis triturated with a mixture of diethyl ether (4 mL) and methanol (1.5 mL)
4. 4
   Filtrationcollected by filtration
5. 5
   Sonstigedried under vacuum at 70° C
6. 6
   FiltrationFurther trituration with water (0.3 mL), filtration
7. 7
   Sonstigedrying under vacuum at 70° C.

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 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).

Quelle