N-(2,2-dimethoxyethyl)cyclohexanamine → N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide

Participants

Reaction Steps

The subtitled compound (3.3 g) was prepared from 3-(3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 17, Step v)] and N-(2,2-dimethoxyethyl)cyclohexanamine using a similar method to that described in Example 12, Step iii). MS [M+H-MeOH]+=430 (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 7.97 (s, 1H), 7.81 and 7.80 (2×s, 1H), 7.19 (m, 1H), 7.09 (dt, J=10.0, 1.9 Hz, 1H), 6.80 (m, 1H), 4.52 and 4.36 (2×t, J=5.0 Hz, 1H), 4.00 and 3.64 (2×tt, J=3.6 and 11.7 Hz, 1H), 3.902 and 3.898 (2×s, 3H), 3.76-3.64 (m, 4H), 3.34 (s, 3H), 3.33 and 3.25 (2×d, J=5.1 Hz, 2H), 3.32 (s, 3H), 2.85 and 2.84 (2×t, J=6.2 Hz, 2H), 2.65 and 2.63 (2×t, J=6.1 Hz, 2H), 1.79-1.69 (m, 2H), 1.68-1.49 (m, 3H), 1.49-1.19 (m, 4H), 1.16-1.01 (m, 1H); a ˜1:1 mixture of rotamers is observed.

Provenance & Evidence