2-(4-Chlorophenyl)-2-methylpropionic acid → N-{5-[1-(3-{[2-(4-chlorophenyl)-2-methylpropanoyl]amino}propyl)-4-piperidinyl]-2-fluorophenyl}butanamide

HRID 1269287Notes

Reaction equation

HRID 1269287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:25]=[CH:26][C:27]([F:36])=[C:28]([NH:30][C:31](=[O:35])[CH2:32][CH2:33][CH3:34])[CH:29]=2)[CH2:20][CH2:19]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([NH:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][CH:21]([C:24]3[CH:25]=[CH:26][C:27]([F:36])=[C:28]([NH:30][C:31](=[O:35])[CH2:32][CH2:33][CH3:34])[CH:29]=3)[CH2:22][CH2:23]2)=[O:11])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 804062-(4-Chlorophenyl)-2-methylpropionic acidHCID 21957132N-{5-[1-(3-aminopropyl)4-piperidinyl]-2-fluorophenyl}butanamide

Product 1

HCID 21957263N-{5-[1-(3-{[2-(4-chlorophenyl)-2-methylpropanoyl]amino}propyl)-4-piperidinyl]-2-fluorophenyl}butanamide

Procedure

Example 110 was prepared from 2-(4-chlorophenyl)-2-methylpropanoic 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 8.31–8.12 (m, 1H), 7.44–7.15 (m, 5H), 7.12–6.94 (m, 1H), 6.75–6.61 (br, 1H), 6.61–6.46 (br, 1H), 3.35–3.12 (m, 4H), 2.70–2.47 (m, 3H), 2.46–2.35 (m, 2H), 2.35–2.21 (m, 2H), 1.92–1.67 (m, 8H), 1.54 (s, 6H), 1.02 (t, 3H, J=7.2 Hz); ESMS m/e: 502.3 (M+H)+.

Sources & evidence

ORD record
ord-ad4dcf22fc924d23bbc953d5d8a1e5e0
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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