3-Furanol, tetrahydro- → HCID 42610017, compound

Participants

Reaction Steps

To a solution of the starting 2-(4-hydroxyphenyl)-N-((1R)-1-{5-[(2,2,2-trifluoroethyl)amino]pyridin-2-yl}ethyl)acetamide (60 mg, 0.17 mmol) in 0.5 ml of dry THF was added the 3-Hydroxytetrahydrofuran (14.92 mg, 0.169 mmol), Di-tert-butyl azodicarboxylate (58.5 mg, 0.254 mmol) and triphenylphosphine (66.6 mg, 0.254 mmol). The mixture was stirred at room temperature for Overnight. The reaction mixture was washed with saturated sodium bicarbonate solution and brine. Organics were extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated in vacuo. Purification by reverse phase chromatography gave 2-[4-(tetrahydrofuran-3-yloxy)phenyl]-N-((1R)-1-{5-[(2,2,2-trifluoroethyl)amino]pyridin-2-yl}ethyl)acetamide as a white solid (0.050 g, 70%). 1H NMR (CDCl3, 400 MHz) δ 8.212 (d, J=2.38 Hz, 1H); 7.189 (m, 4H); 6.830 (m, 2H); 6.624 (d, J=7.15 Hz, 1H); 5.103 (quintet, J=6.95 Hz, 1H); 4.924 (m, 1H); 4.379 (dd, J=8.06, 15.93 Hz, 2H); 3.999 (m, 3H); 3.905 (m, 1H); 3.519 (s, 2H); 2.187 (m, 2H); 1.387 (d, J=6.78 Hz, 3H); MS (ES): m/z 425.2 (M+H). FLIPR alpha1I IP=91 nM.

Provenance & Evidence