Triethylamine → Methyl 4-(4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole (150 mg, 0.344 mmol) and triethylamine (0.120 mL, 0.861 mmol) in CH2Cl2 (3 mL) at 0° C. was added methyl 4-(chlorosulfonyl)butanoate (104 mg, 0.517 mmol). The reaction mixture was stirred at 0° C. for 15 min, then at rt for 2 h. The reaction mixture was quenched with sat. aq. NaHCO3 (4 mL) and extracted with CH2Cl2 (3×5 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated. The crude product was purified by column chromatography (silica gel, CH2Cl2-EtOAc gradient 0 to 55% EtOAc) to afford methyl 4-(4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)butanoate (84 mg, 0.14 mmol, 41% yield) as a white solid. LCMS (m/z)=600 (M+H)+.

Provenance & Evidence