Hydroxy[bis(4-methylphenyl)]acetic acid → N-(2,4-difluoro-5-{1-[3-({hydroxy[bis(4-methylphenyl)]acetyl}amino)propyl]-4-piperidinyl}phenyl)-2-methylpropanamide

HRID 1269329Notes

Reaction equation

HRID 1269329 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[C:31]([F:43])=[CH:32][C:33]([F:42])=[C:34]([NH:36][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])[CH:35]=2)[CH2:26][CH2:25]1>>[F:42][C:33]1[CH:32]=[C:31]([F:43])[C:30]([CH:27]2[CH2:26][CH2:25][N:24]([CH2:23][CH2:22][CH2:21][NH:20][C:3](=[O:4])[C:2]([OH:1])([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[C:6]3[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=3)[CH2:29][CH2:28]2)=[CH:35][C:34]=1[NH:36][C:37](=[O:41])[CH:38]([CH3:39])[CH3:40]

Participants

3

Reactant 2

HCID 229097Hydroxy[bis(4-methylphenyl)]acetic acidHCID 16757466N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2,4-difluorophenyl}-2-methylpropanamide

Product 1

HCID 18446853N-(2,4-difluoro-5-{1-[3-({hydroxy[bis(4-methylphenyl)]acetyl}amino)propyl]-4-piperidinyl}phenyl)-2-methylpropanamide

Procedure

Example 159 was prepared from hydroxy[bis(4-methylphenyl)]acetic acid and N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2,4-difluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 12: 1H NMR (400 MHz, CDCl3) δ 8.78–8.62 (s, br, 1 H), 8.37 (t, 1 H, J=9.6 Hz), 7.40 (d, 4 H, J=8.4 Hz), 7.28 (s, 1 H), 7.09 (d, 4 H, J=8.0 Hz), 6.84–6.74 (m, 1 H), 5.14–4.82 (br, 1 H), 3.55–3.40 (m, 2 H), 3.11–2.94 (m, 2 H), 2.94–2.78 (m, 1 H), 2.59–2.46 (m, 2 H), 2.46–2.36 (m, 1 H), 2.31 (s, 6 H), 2.11–1.91 (m, 4 H), 1.77–1.61 (m, 4 H), 1.04 (d, 6 H, J=7.2 Hz); ESMS m/e: 578.4 (M+H)+.

Sources & evidence

ORD record
ord-f9df4e4249164be7ac97364302ffe9b1
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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