Reaktion #643045

Reaktionsgleichung

1-tert-butyl 4-methyl 4-(3-chloropyrazin-2-yl)piperidine-1,4-dicarboxylate

4-(benzo[d]thiazol-2-ylamino)phenol

cesium carbonate

DMSO

→

1-tert-butyl 4-methyl 4-(3-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyrazin-2-yl)piperidine-1,4-dicarboxylate

Ausbeute 39.3%

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled to rt
2. 2
   Extraktionextracted with EtOAc (3×5 mL)
3. 3
   TrocknenThe combined organic layers were dried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified by RPHPLC

Vorschrift

To a vial with 1-tert-butyl 4-methyl 4-(3-chloropyrazin-2-yl)piperidine-1,4-dicarboxylate (58 mg, 0.163 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (39.5 mg, 0.163 mmol), and cesium carbonate (106 mg, 0.326 mmol) under N2 is added DMSO (1.0 mL). The reaction is heated to 100° C. in an oil bath 3 h. The reaction was cooled to rt, added to H2O (5 mL) and extracted with EtOAc (3×5 mL). The combined organic layers were dried (MgSO4) and concentrated. The residue was purified by RPHPLC to give 1-tert-butyl 4-methyl 4-(3-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyrazin-2-yl)piperidine-1,4-dicarboxylate (36 mg, 0.064 mmol, 39.3% yield) as a white solid. [M+1]=562.1. IC50 (uM) +++++.

Quelle