2,2-Bis(4-fluorophenyl)acetic acid → N-{5-[1-(3-{[bis(4-fluorophenyl)acetyl]amino}propyl)-4-piperidinyl]-2,4-difluorophenyl}-2-methylpropanamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[C:30]([F:42])=[CH:31][C:32]([F:41])=[C:33]([NH:35][C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])[CH:34]=2)[CH2:25][CH2:24]1>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([NH:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([C:29]3[C:30]([F:42])=[CH:31][C:32]([F:41])=[C:33]([NH:35][C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])[CH:34]=3)[CH2:27][CH2:28]2)=[O:11])=[CH:13][CH:14]=1Participants
3
Procedure
Example 165 was prepared from bis(4-fluorophenyl)acetic acid and N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2,4-difluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.25 (t, 1 H, J=8.4 Hz), 7.67–7.57 (m, 1 H), 7.51 (s, 1 H), 7.36–7.25 (m, 4 H), 7.03–6.91 (m, 4 H), 6.81 (t, 1 H, J=9.6 Hz), 4.81 (s, 1 H), 3.45–3.31 (m, 2 H), 2.92 (m, 2 H), 2.83–2.67 (m, 1 H), 2.63–2.47 (m, 1 H), 2.47–2.33 (m, 2 H), 2.05–1.90 (m, 2 H), 1.82–1.72 (m, 2 H), 1.72–1.56 (m, 4 H), 1.22 (d, 6 H, J=6.8 Hz); ESMS m/e: 570.2 (M+H)+.
Sources & evidence
- ORD record
- ord-e55f9480316c4fe3a410d57416e46859
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
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