2,2-Difluoro-2-phenylacetic acid → N-{3-[1-(3-{[difluoro(phenyl)acetyl]amino}propyl)-4-piperidinyl]-4-fluorophenyl}-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:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH:26]=[CH:27][C:28]=2[F:29])[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:30][C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])[CH:26]=[CH:27][C:28]=2[F:29])[CH2:19][CH2:18]1)=[O:5]Participants
3
Procedure
Example 136 was prepared from 2,2-difluoro-2-phenylacetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-fluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 9.11 (s, 1H), 7.61–7.56 (m, 2H), 7.41–7.34 (m, 4H), 7.21–7.17 (m, 1H), 7.14 (s, 1H), 6.88 (t, 1H, J=9.5 Hz), 3.39 (q, 2H, J=5.7 Hz), 3.08–3.01 (m, 2H), 2.84–2.74 (m, 1H), 2.50 (t, 2H, J=5.1 Hz), 2.38 (septet, 1H, J=7.2 Hz), 2.08–1.99 (m, 2H), 1.81–1.73 (m, 4H), 1.72–1.64 (m, 2H), 1.17 (d, 6H, J=7.2 Hz); ESMS m/e: 476.2 (M+H)+.
Sources & evidence
- ORD record
- ord-69799f9357874e40af4e94ed80ac11ad
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
Loading…