Reaktion #45066

Reaktionsgleichung

trimethylaluminium

1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-amine

ethyl 4-(piperazin-1-yl)benzoate

→

N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(piperazin-1-yl)benzamide

Ausbeute 22.5%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with methanol (20 mL)
2. 2
   Filtrationfiltered
3. 3
   Sonstigeevaporated
4. 4
   Sonstigeto afford tan solid
5. 5
   SonstigeThe crude product was purified by silica column chromatography
6. 6
   Wascheneluting with a gradient of 0 to 10% MeOH in DCM and 0.1% ammonia
7. 7
   SonstigePure fractions were evaporated to dryness

Vorschrift

A 2M solution of trimethylaluminium in toluene (6.25 mL, 12.50 mmol) was added dropwise to a stirred solution of and 1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-amine (1.367 g, 5.00 mmol) and ethyl 4-(piperazin-1-yl)benzoate (1.171 g, 5 mmol) in toluene (20 mL) at 4° C., over a period of 5 mins under nitrogen. The resulting solution was stirred at 20° C. for 18 h. The reaction mixture was quenched with methanol (20 mL), filtered and evaporated to afford tan solid. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in DCM and 0.1% ammonia. Pure fractions were evaporated to dryness to afford N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(piperazin-1-yl)benzamide (0.520 g, 22.53%) as a white solid.

Quelle