DL-2-(4-chlorophenyl)propanoic acid → N-{3-[1-(3-{[2-(4-Chlorophenyl)propanoyl]amino}propyl)-4-piperidinyl] phenyl}cyclopropanecarboxamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([C:23]2[CH:24]=[C:25]([NH:29][C:30]([CH:32]3[CH2:34][CH2:33]3)=[O:31])[CH:26]=[CH:27][CH:28]=2)[CH2:19][CH2:18]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[C:9]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]3[CH:24]=[C:25]([NH:29][C:30]([CH:32]4[CH2:34][CH2:33]4)=[O:31])[CH:26]=[CH:27][CH:28]=3)[CH2:19][CH2:18]2)=[O:11])=[CH:6][CH:7]=1Participants
3
Procedure
Example 116 was prepared from 2-(4-chlorophenyl)propanoic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}cyclopropanecarboxamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 8.15–7.95 (br, 1H), 7.63–7.44 (br, 1H), 7.39–7.12 (m, 7H), 6.85 (d, 1H, J=6.8 Hz), 3.74–3.55 (m, 1H), 3.45–3.22 (m, 2H), 3.22–3.12 (m, 1H), 3.12–3.00 (m, 1H), 2.66–2.40 (m, 3H), 2.29–2.09 (m, 2H), 1.92–1.63 (m, 6H), 1.64–1.51 (m, 1H), 1.47 (d, 3H, J=6.8 Hz), 1.18–0.98 (m, 2H), 0.91–0.74 (m, 2H); ESMS m/e: 468.2 (M+H)+; Anal. Calc. for (HCl salt) C27H35Cl2N3O2.0.28CHCl3: C, 60.91; H, 6.61; N, 7.81; Found: C, 60.66; H, 6.90; N, 8.19.
Sources & evidence
- ORD record
- ord-4466b797e7b74c219b7000e35b8e4f6d
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
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