trans-3,4-Difluorocinnamic acid → 2-[4-(1H-Indol-3-yl)-cyclohexylamino]-2-[1-(trans-3,4-difluorocinnamoyl)-piperidin-4-yl]-acetamide
Reaktionsgleichung
Cl.Cl.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:20]([NH2:22])=[O:21])[CH2:14][CH2:13]2)=[CH:4]1.[F:29][C:30]1[CH:31]=[C:32]([CH:38]=[CH:39][C:40]=1[F:41])/[CH:33]=[CH:34]/[C:35](O)=[O:36]>>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([CH:23]3[CH2:24][CH2:25][N:26]([C:35](=[O:36])/[CH:34]=[CH:33]/[C:32]4[CH:38]=[CH:39][C:40]([F:41])=[C:30]([F:29])[CH:31]=4)[CH2:27][CH2:28]3)[C:20]([NH2:22])=[O:21])[CH2:14][CH2:13]2)=[CH:4]1Komponenten
Versuchsvorschrift
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).
Aufarbeitung
- customgiving a yellow solid for the more polar chromatographic product, which
- additiona mixture of stereoisomers by NMR and LCMS
Quellen und Nachweise
- ORD-Eintrag
- ord-0927d8da993c42ce83a86ce5c79a7407
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08921559B2
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