Reaction Steps
The title compound was prepared by the method outlined for Example 1 using 4-bromo-2-(cyclopentyloxy)-1-ethoxybenzene as the aryl halide and tert-butyl (2R)-2-(1H-pyrazol-1-ylmethyl)piperazine-1-carboxylate as amine component. The intermediate and title compound were isolated as oils (76 and 77%). 1H NMR (CDCl3) 7.55 (d, J=1.6, 1H), 7.43 (d, J=1.9, 1H), 6.80 (d, J=8.6, 1H), 6.53 (d, J=2.8, 1H), 6.42 (dd, J=8.6, 2.7, 1H), 6.26 (t, J=2.2, 1H), 4.76-4.73 (m, 1H), 4.23 (dd, J=13.7, 4.9, 1H), 4.14 (dd, J=13.5, 7.6, 1H), 3.98 (q, J=7.1, 2H), 3.42-3.27 (m, 3H), 3.09 (dt, J=11.8, 3.0, 1H), 2.96 (td, J=10.8, 3.0, 1H), 2.75 (td, J=11.1, 3.1, 1H), 2.49 (t, J=9.6, 1H), 1.89-1.81 (m, 6H), 1.62-1.59 (m, 2H), 1.37 (t, J=6.8, 3H). 13C NMR 149.0, 146.7, 144.0, 139.9 (CH), 130.1 (CH), 116.1 (CH), 108.9 (CH), 107.3 (CH), 105.6 (CH), 80.8, (CH), 65.7 (CH2), 55.1 (CH), 55.0 (CH), 54.4 (CH2), 51.0 (CH2), 45.1 (CH2), 32.8 (CH2), 23.9 (CH2), 15.1 (CH3). LC/MS (Method B) 4.40 and 2.55 min, [M+1]+ 471 and 371.
