Reaktion #1967245

Reaktionsgleichung

tert-butyl benzo[d]thiazol-2-yl(4-(3-bromopyridin-2-yloxy)phenyl)carbamate

1-(piperazin-1-yl)ethanone

binap

cesium carbonate

→

tert-butyl 4-(3-(4-acetylpiperazin-1-yl)pyridin-2-yloxy)phenyl(benzo[d]thiazol-2-yl)carbamate

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction
2. 2
   Temperaturto cool to room temperature
3. 3
   SonstigeSolvent was evaporated
4. 4
   SonstigeThe crude product was purified by reverse-phase preparative HPLC
5. 5
   Sonstigeover 15 min

Vorschrift

To a round bottomed flask was added tert-butyl benzo[d]thiazol-2-yl(4-(3-bromopyridin-2-yloxy)phenyl)carbamate (0.2713 g, 0.544 mmol), 1-(piperazin-1-yl)ethanone (0.140 g, 1.089 mmol), Pd2(dba)3 (0.050 g, 0.054 mmol), binap (0.068 g, 0.109 mmol), and cesium carbonate (0.174 mL, 2.177 mmol) in toluene to stir at 100° C. overnight. Reaction was allowed to cool to room temperature. Solvent was evaporated. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Synergi column, 4 micron, MAX-RP, 80 Å, 150×30 mM, 0.1% TFA in ACN/H2O, gradient 10% to 100% over 15 min to provide tert-butyl 4-(3-(4-acetylpiperazin-1-yl)pyridin-2-yloxy)phenyl(benzo[d]thiazol-2-yl)carbamate (MS 545.6). It was taken up in DCM and TFA was added. After purification the title compound was obtained. MS (ESI, pos. ion) m/z: 446.1 (M+1). IC50 (uM) +++++.

Quelle