Sodium hydride → HCID 71523440, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((1S,2R)-2-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]cyclopropyl)ethanol (30 mg, 0.119 mmol) in DMF (1 mL) was added NaH (60%, 7.2 mg, 0.179 mmol) at RT. The mixture was stirred for 15 min. 1-fluoro-4-(methylsulfonyl)benzene (20.8 mg, 0.119 mmol) was added to the reaction mixture. It was heated at 50° C. for 3 hours. The reaction was quenched with water, extracted with EtOAc. The organic layer was dried by sodium sulfate and concentrated. The residue was purified by Mass directed RPHPLC. The product fraction was basified with 1 M sodium bicarbonate aq. solution, extracted with EtOAc. Solvent was removed under vacuum to yield the Example 4. LCMS calc: 405.47; obs: 406.04 (M+1); Human GPR119 EC50: 175.6 nM. 1H NMR (CDCl3, 500 MHz) 7.90 (d, 2H), 7.02 (d, 2H), 4.15 (m, 2H), 3.05 (s, 3H), 2.97 (m, 4), 2.34 (m, 2H), 2.18 (m, 1H), 1.78 (m, 2H), 1.45-1.58 (m, 3H), 0.96 (m, 1H), 0.82 (m, 1H), 0.65 (m, 2H), −0.88 (m, 1H)

Provenance & Evidence