2-Chloro-4-fluorobenzoyl chloride → HCID 69066341, compound

Participants

Reaction Steps

Using a method similar to Example 5, using 2-chloro-4-fluoro-benzoyl chloride (0.054 mL, 0.420 mmol) and 3-(1-ethyl-piperidin-4-yloxy)-phenylamine (preparation 29) gives the title compound as the free base (131 mg, 91%). Following a method similar to Example 2 gives the title compound as the hydrochloride salt (130 mg, white solid). Mp: 91° C.; mass spectrum (free base, ion spray): m/z=377.2 (M+1); 1H NMR (free base, CDCl3): 8.14 (bs, N—H), 7.68 (dd, J=6.1 Hz, 8.7 Hz, 1H), 7.40 (bs, 1H), 7.21 (t, J=8.1 Hz, 1H), 7.14 (dd, J=2.5 Hz, 8.3 Hz, 1H), 7.06-7.01 (m, 2H), 6.70 (dd, J=2.4 Hz, 8.3 Hz, 1H), 4.38-4.31 (m, 1H), 2.75-2.67 (bm, 2H), 2.41 (q, J=7.1 Hz, 2H), 2.33-2.24 (bm, 2H), 2.04-1.97 (bm, 2H), 1.87-1.78 (bm, 2H), 1.08 (t, J=7.4 Hz, 3H); Analysis calculated for C20H23Cl2FN2O2.0.25H2O: C, 57.49; H, 5.67; N, 6.70. Found C, 57.45; H, 5.31; N, 6.59.

Provenance & Evidence