Sodium hydride → HCID 178420807, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-fluoro-3-(tetrahydro-pyran-4-yl)-pyridine, as prepared in preparation 1a, (200 mg, 1.1 mmol), 4-benzothiazol-2-yl-cyclohexanol (257 mg, 1.1 mmol) and NaH (60%) (53 mg, 2.2 mmol) in DMA (4 mL) was heated to 120° C. for 2 h. Then the reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3×15 mL), washed with brine, dried over Na2SO4. After concentration, the residue was purified by Prep-TLC and then Prep-HPLC to give trans-2-{4-[3-(Tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclohexyl}-benzothiazole (14 mg, 0.036 mmol, 3.2% yield) and cis-2-{4-[3-(Tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclohexyl}-benzothiazole (15 mg, 0.038 mmol, 3.5%). [M+1] 395 each. IC50 (uM): (trans) 0.408 and (cis) 0.584.

Provenance & Evidence