4-Methyl-alpha-(4-methylphenyl)benzeneacetic acid → N-{3-[1-(3-{[bis(4-methylphenyl)acetyl]amino}propyl)-4-piperidinyl]-4-fluorophenyl}-2-methylpropanamide
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[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[CH:30]=[C:31]([NH:36][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])[CH:32]=[CH:33][C:34]=2[F:35])[CH2:25][CH2:24]1>C(Cl)(Cl)Cl>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[C:9]([NH:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[CH:30]=[C:31]([NH:36][C:37](=[O:41])[CH:38]([CH3:39])[CH3:40])[CH:32]=[CH:33][C:34]=3[F:35])[CH2:25][CH2:24]2)=[O:11])=[CH:13][CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Example 132 was prepared from bis(4-methylphenyl)acetic 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 7.72 (s, 1H), 7.36–7.31 (m, 1H), 7.28–7.21 (m, 1H), 7.12–7.07 (m, 3H), 7.03–6.99 (m, 5H), 6.86–6.80 (m, 1H), 6.79–6.75 (m, 1H), 4.74 (s, 1H), 3.33–3.25 (m, 2H), 2.85–2.77 (m, 2H), 2.72–2.62 (m, 1H), 2.40 (septet, 1H, J=6.7 Hz), 2.28 (t, 2H, J=6.6 Hz), 2.21 (m, 6H), 1.94–1.84 (m, 2H), 1.65–1.52 (m, 6H), 1.71 (d, 6H, J=6.6 Hz); ESMS m/e: 544.3 (M+H)+; Anal. Calc. for C34H42FN3O2.HCl.0.10 CHCl3: C, 70.17; H, 7.35; N, 7.10. Found: C, 70.35; H, 6.99; N, 7.10.
Sources & evidence
- ORD record
- ord-887d4a82256240ee921597314dcecc2a
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199135B2
Reaction notes
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