Reaktion #307768

Reaktionsgleichung

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

potassium carbonate

4-sulfonylaminoethyl benzene boronic acid

HCl

→

title compound

Ausbeute 72.1%

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

Ausbeute 72.1%

Lösungsmittel

acetonitrile

water

N,N-dimethylacetamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige, then purify by SCX-2® chromatography
2. 2
   Waschenwashing with methanol
3. 3
   WaschenElute with 2 M ammonia in methanol
4. 4
   Einengenconcentrate
5. 5
   SonstigeRecrystallize from DMSO:methanol (1:1)
6. 6
   Filtrationfilter
7. 7
   Waschenwash with diethyl ether
8. 8
   Sonstigeto give a whitish powder

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 (331 mg, 2.4 mmol), 4-sulfonylaminoethyl benzene boronic acid (292 mg, 1.2 mmol), tetrakis(triphenylphosphine)palladium(0) (0.0050 g, 0.0058 mmol), then water (2 mL) and degas with nitrogen for 10 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. Recrystallize from DMSO:methanol (1:1), filter and wash with diethyl ether, to give a whitish powder. Dissolve the powder 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 yellow powder (365 mg, 71%). MS (ES): m/z=470 [M+H]+.

Quelle