Reaktion #45086

Reaktionsgleichung

2,3,4,6,7,8,9,9a-Octahydro-1H-pyrido[1,2-a]pyrazine

5-chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide

→

desired compound

5-(1,3,4,6,7,8,9,9a-Octahydropyrido[2,1-c]pyrazin-2-yl)-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide

Lösungsmittel

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude product was purified by ion exchange chromatography
2. 2
   WaschenThe desired product was eluted from the column
3. 3
   Sonstigeto afford impure material
4. 4
   SonstigeThe concentrated eluant was purified by preparative HPLC
5. 5
   Sonstigeto obtain the free base

Vorschrift

2,3,4,6,7,8,9,9a-Octahydro-1H-pyrido[1,2-a]pyrazine (477 mg, 3.40 mmol) was added in one portion to 5-chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide (659 mg, 1.70 mmol) in anhydrous dimethylsulfoxide (1.70 ml) at 25° C. The resulting solution was stirred at 100° C. for 18 h. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH to afford impure material. The concentrated eluant was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% formic acid) and MeCN as eluents. The sample was then put through a basic HPLC system to obtain the free base. Fractions containing the desired compound were evaporated to dryness to afford the title compound (395 mg, 47%) as a cream solid.

Quelle