Reaktion #307770

Reaktionsgleichung

3′-chloro-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl

potassium carbonate

2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetamide

HCl

→

title compound

Ausbeute 37.3%

2-{4-[4-(1,5-Dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl]-phenyl}-acetamide hydrochloride

Ausbeute 37.3%

Lösungsmittel

acetonitrile

water

N,N-dimethylacetamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethen purify by SCX-2® chromatography
2. 2
   Waschenwashing with methanol
3. 3
   WaschenElute with 2 M ammonia in methanol
4. 4
   Einengenconcentrate
5. 5
   SonstigePurify
6. 6
   Waschensilica gel chromatography (eluting with 5:95 to 20:80 methanol:DCM)
7. 7
   Sonstigeto give an oil

Vorschrift

Dissolve 3′-chloro-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (307 mg, 1.0 mmol) in N,N-dimethylacetamide (4 mL). Add potassium carbonate (332 mg, 2.4 mmol), 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetamide (313 mg, 1.2 mmol), tetrakis(triphenylphosphine)palladium(0) (0.0050 g, 0.0058 mmol), then water (2 mL) and degas with nitrogen for 5 min. Heat at 120° C. for 20 hr. then purify by SCX-2® chromatography washing with methanol. Elute with 2 M ammonia in methanol and concentrate. Purify using silica gel chromatography (eluting with 5:95 to 20:80 methanol:DCM) to give an oil. Dissolve the free base in acetonitrile and convert to the hydrochloride salt by adding 2 M aq HCl solution. Add water and lyophilize to give the title compound as a light yellow powder (0.165 g, 37%). MS (ES): m/z=406 [M+H]+.

Quelle