2,2-Diphenylbutyric acid → N-(3-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)-2,2-diphenylbutanamide
Reaction equation
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:11][CH3:12])[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:30]=[C:31]([NH:35][C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])[CH:32]=[CH:33][CH:34]=2)[CH2:25][CH2:24]1>>[C:36]([NH:35][C:31]1[CH:30]=[C:29]([CH:26]2[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][CH2:20][NH:19][C:8](=[O:9])[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH3:12])[CH2:24][CH2:25]2)[CH:34]=[CH:33][CH:32]=1)(=[O:40])[CH:37]([CH3:38])[CH3:39]Participants
3
Procedure
Example 12 was prepared from 2,2-diphenylbutanoic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methyl propanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.44–7.39 (m, 2H), 7.37–7.28 (m, 8H), 7.27–7.20 (m, 3H), 6.89 (d, 1H, J=7.4 Hz), 6.43 (t, 1H, J=4.5 Hz), 3.35–3.27 (m, 2H), 2.90–2.82 (m, 2H), 2.51 (septet, 1H, J=6.8 Hz), 2.49–2.35 (m, 4H), 2.24 (t, 2H, J=6.3 Hz), 1.89 (t, 2H, J=10.2 Hz), 1.75–1.68 (m, 2H), 1.66–1.58 (m, 2H), 1.57–1.45 (m, 2H), 1.24 (d, 6H, J=6.7 Hz), 1.27–1.23 (m, 2H); ESMS m/e: 526.3 (M+H)+.
Sources & evidence
- ORD record
- ord-ed8a2ba7adac434fbea20290b106ba70
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
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