4-(Benzylcarbamoyl)benzeneboronic acid → 4'-[({1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-N-(phenylmethyl)-4-biphenylcarboxamide

Participants

Reaction Steps

The title compound (2 mg, 2%) was prepared from (4-{[(phenylmethyl)amino]carbonyl}phenyl)boronic acid (51 mg, 0.2 mmol) and 4-{[(4-bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine (prepared as in Example 24, Step 1, 76 mg, 0.2 mmol) in a manner similar to Example 1, Step 1, and worked up in a manner similar to Example 9, Step 3. 1H NMR (400 MHz, CDCl3): δ 7.83 (d, 2H, J=8.6 Hz), 7.61 (d, 2H, J=8.6 Hz), 7.54 (d, 2H, J=8.9 Hz), 7.39-7.28 (m, 5H), 6.97 (d, 2H, J=8.8 Hz), 6.41 (t, 1H, J=5.7 Hz), 4.68 (d, 2H, J=5.5 Hz), 4.26-4.16 (m, 2H), 3.88 (d, 2H, J=6.4 Hz), 3.18-3.06 (m, 2H), 2.96-2.85 (m, 1H), 2.13-2.01 (m, 1H), 2.02-1.92 (m, 2H), 1.55-1.40 (m, 2H), 1.29 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 511 (M+H).

Provenance & Evidence