2-(4-Chlorophenyl)-2-methylpropionic acid → Isopropyl 3-[1-(3-{[2-(4-chlorophenyl)-2-methylpropanoyl]amino}propyl)-4-piperidinyl]phenylcarbamate

HRID 2213508Notes

Reaction equation

HRID 2213508 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]=[C:26]([NH:30][C:31](=[O:36])[O:32][CH:33]([CH3:35])[CH3:34])[CH:27]=[CH:28][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[CH2:23][CH2:22][CH:21]([C:24]3[CH:25]=[C:26]([NH:30][C:31](=[O:36])[O:32][CH:33]([CH3:34])[CH3:35])[CH:27]=[CH:28][CH:29]=3)[CH2:20][CH2:19]2)=[O:11])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 804062-(4-Chlorophenyl)-2-methylpropionic acidHCID 21957208Isopropyl 3-[1-(3-aminopropyl)-4-piperidinyl]phenylcarbamate

Product 1

HCID 21957200Isopropyl 3-[1-(3-{[2-(4-chlorophenyl)-2-methylpropanoyl]amino}propyl)-4-piperidinyl]phenylcarbamate

Procedure

Example 142 was prepared from 2-(4-chlorophenyl)-2-methylpropanoic acid and isopropyl 3-[1-(3-aminopropyl)-4-piperidinyl]phenylcarbamate according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.29–7.22 (m, 3H), 7.20–7.11 (m, 3H), 7.09–7.06 (m, 1H), 6.79 (d, 1H, J=7.6 Hz), 6.61 (s, 1H), 6.60–6.50 (m, 1H), 4.94 (septet, 1H, J=6.7 Hz), 4.05 (q, 1H, J=6.8 Hz), 3.24 (q, 2H, J=5.9 Hz), 2.86–2.79 (m, 2H), 2.36 (tt, 1H, J=11.9, 3.2 Hz), 2.27 (t, 2H, J=6.3 Hz), 1.85 (t, 2H, J=11.9 Hz), 1.72–1.66 (m, 2H), 1.60–1.52 (m, 3H), 1.48 (s, 6H), 1.23 (d, 6H, J=6.7 Hz); ESMS m/e: 500.2 (M+H)+.

Sources & evidence

ORD record
ord-303952bad954424396404a36b28122af
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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