Reaktion #45092

Reaktionsgleichung

trimethylaluminium

ethyl 4-(3,3-dimethylpiperazin-1-yl)benzoate

5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine

sodium sulphite

→

title compound

Ausbeute 10.5%

N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]-4-(3,3-dimethylpiperazin-1-yl)benzamide

Ausbeute 10.5%

Lösungsmittel

acetone

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred for 1 h
2. 2
   Filtrationthe solid filtered off
3. 3
   WaschenThe solid was washed with 10% MeOH/DCM
4. 4
   Sonstigethe combined organics evaporated to dryness
5. 5
   SonstigeThe crude product was purified by preparative HPLC
6. 6
   workup.ADDITIONFractions containing the desired compound
7. 7
   Sonstigewere evaporated to dryness

Vorschrift

A 2M solution of trimethylaluminium in toluene (0.691 mL, 1.38 mmol) was added dropwise to a stirred solution of ethyl 4-(3,3-dimethylpiperazin-1-yl)benzoate (145 mg, 0.55 mmol) and 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine (138 mg, 0.55 mmol) in toluene (5 mL) at 20° C., over a period of 5 mins under nitrogen. The resulting solution was stirred at 20° C. for 24 h. This was diluted with acetone (25 ml) and an excess of damp solid sodium sulphite was added. The mixture was stirred for 1 h and the solid filtered off. The solid was washed with 10% MeOH/DCM and the combined organics evaporated to dryness. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (27.0 mg, 10.49%) as a colourless gum.

Quelle