trans-3,4-Difluorocinnamic acid → 2-[4-(1H-Indol-3-yl)-cyclohexylamino]-2-[1-(trans-3,4-difluorocinnamoyl)-piperidin-4-yl]-acetamide

Participants

Reaction Steps

The title compound was prepared from the product of Example 1, step J (142 mg, 0.333 mmol), and trans-3,4-difluorocinnamic acid, by the method of Example 1, step K, giving a yellow solid for the more polar chromatographic product, which was still a mixture of stereoisomers by NMR and LCMS. Mass spectrum (LCMS, ESI pos.) calcd. for C30H34F2N4O2: 521 (M+H). Found: 521.2. 1H NMR (CHLOROFORM-d) δ: 7.95-8.03 (m, 1H), 7.62 (dd, J=7.7, 3.9 Hz, 1H), 7.55 (dd, J=15.4, 6.8 Hz, 1H), 7.30-7.39 (m, 2H), 7.06-7.24 (m, 4H), 6.90-7.02 (m, 1H), 6.75-6.86 (m, J=15.4, 6.1 Hz, 1H), 5.54 (d, J=3.5 Hz, 1H), 4.69-4.90 (m, 1H), 4.14 (br. s., 1H), 3.02-3.22 (m, J=15.4 Hz, 2H), 2.73-2.85 (m, 1H), 2.56-2.73 (m, 1H), 2.45 (tt, J=11.0, 3.4 Hz, 1H), 2.04-2.23 (m, 3H), 1.89-2.04 (m, 2H), 1.66-1.88 (m, 5H), 1.14-1.54 (m, 6H).

Provenance & Evidence