1-(4-Fluorophenyl)cyclopentanecarboxylic acid → N-(3-{4-[3-(butyrylamino)-4-fluorophenyl]-1-piperidinyl}propyl)-1-(4-fluorophenyl)cyclopentanecarboxamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:27]=[CH:28][C:29]([F:38])=[C:30]([NH:32][C:33](=[O:37])[CH2:34][CH2:35][CH3:36])[CH:31]=2)[CH2:22][CH2:21]1>>[C:33]([NH:32][C:30]1[CH:31]=[C:26]([CH:23]2[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][CH2:17][NH:16][C:13]([C:8]3([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:9][CH2:10][CH2:11][CH2:12]3)=[O:15])[CH2:21][CH2:22]2)[CH:27]=[CH:28][C:29]=1[F:38])(=[O:37])[CH2:34][CH2:35][CH3:36]Participants
3
Procedure
Example 107 was prepared from 1-(4-fluorophenyl)cyclopentanecarboxylic acid and N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2-fluorophenyl}butanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.30–8.13 (m, 1H), 8.09–7.95 (br, 1H), 7.47–7.26 (m, 3H), 7.08–6.87 (m, 3H), 6.75–6.54 (br, 1H), 3.30–3.07 (m, 4H), 2.59–2.44 (m, 3H), 2.44–2.33 (m, 2H), 2.33–2.19 (m, 2H), 1.99–1.69 (m, 16H), 1.02 (t, 3H, J=7.2 Hz); ESMS m/e: 512.3 (M+H)+.
Sources & evidence
- ORD record
- ord-9ea67b6566f648a0bf34d84b7d11bf33
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
Loading…