Hydroxy[bis(4-methylphenyl)]acetic acid → N-(3-{1-[3-({hydroxy[bis(4-methylphenyl)]acetyl}amino)propyl]-4-piperidinyl}-4-methylphenyl)-2-methylpropanamide

HRID 1269327Notes

Reaction equation

HRID 1269327 reaction equation
[OH:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[C:3](O)=[O:4].[NH2:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:31]=[C:32]([NH:37][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])[CH:33]=[CH:34][C:35]=2[CH3:36])[CH2:26][CH2:25]1>>[OH:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[C:3]([NH:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:31]=[C:32]([NH:37][C:38](=[O:42])[CH:39]([CH3:40])[CH3:41])[CH:33]=[CH:34][C:35]=2[CH3:36])[CH2:26][CH2:25]1)=[O:4]

Participants

3

Reactant 2

HCID 229097Hydroxy[bis(4-methylphenyl)]acetic acidHCID 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 18446865N-(3-{1-[3-({hydroxy[bis(4-methylphenyl)]acetyl}amino)propyl]-4-piperidinyl}-4-methylphenyl)-2-methylpropanamide

Procedure

Example 157 was prepared from hydroxy[bis(4-methylphenyl)]acetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide according to the procedures described in Scheme 12: 1H NMR (400 MHz, CDCl3) δ 8.80–8.59 (s, br, 1 H), 7.91 (s, 1 H), 7.42 (d, 4 H, J=8.4 Hz), 7.15 (s, 1 H), 7.09 (d, 4 H, J=8.0 Hz), 7.04 (d, 1 H, J=8.0 Hz), 6.96–6.78 (br, 1 H), 5.30–5.05 (br, 1 H), 3.55–3.41 (m, 2 H), 3.15–3.00 (m, 2 H), 2.82–2.64 (m, 1 H), 2.59–2.46 (m, 2 H), 2.40–2.27 (m, 1 H), 2.30 (s, 6 H), 2.28 (s, 3 H), 2.17–1.95 (m, 4 H), 1.83–1.56 (m, 4 H), 1.02 (d, 6 H, J=6.8 Hz); ESMS m/e: 556.4 (M+H)+.

Sources & evidence

ORD record
ord-41aa8ef3062c41b9bd60237c55f74f58
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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