2,2-Difluoro-2-phenylacetic acid → N-{3-[1-(3-{[difluoro(phenyl)acetyl]amino}propyl)-4-piperidinyl]phenyl}-2-methylpropanamide
Reaction equation
[F:1][C:2]([F:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=O.[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](=[O:34])[CH:31]([CH3:33])[CH3:32])[CH:26]=[CH:27][CH:28]=2)[CH2:19][CH2:18]1>>[F:12][C:2]([F:1])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH: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](=[O:34])[CH:31]([CH3:32])[CH3:33])[CH:26]=[CH:27][CH:28]=2)[CH2:19][CH2:18]1)=[O:5]Participants
3
Procedure
Example 125 was prepared from 2,2-difluoro-2-phenylacetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methylpropanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.71 (s, 1H), 7.65–7.62 (m, 2H), 7.50 (s, 1H), 7.47–7.40 (m, 3H), 7.35 (d, 1H, J=7.6 Hz), 7.22 (t, 1H, J=7.2 Hz), 6.95 (d, 1H, J=7.8 Hz), 3.45 (q, 2H, J=5.3 Hz), 3.10 (d, 2H, J=10.9 Hz), 2.59–2.45 (m, 4H), 2.11–2.02 (m, 2H), 1.89–1.71 (m, 6H), 1.20 (d, 6H, J=6.9 Hz); ESMS m/e: 458.4 (M+H)+.
Sources & evidence
- ORD record
- ord-d966d95d99504369a437537911f216b1
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
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