(2S)-2-(4-chlorophenyl)propanoic acid → (2S)-2-(4-chlorophenyl)-N-(3-{4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinyl}propyl)propanamide

HRID 1269332Notes

Reaction equation

HRID 1269332 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([C:23]2[CH:24]=[C:25]([NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH:26]=[CH:27][C:28]=2[CH3:29])[CH2:19][CH2:18]1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([CH3:12])[C:9]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]3[CH:24]=[C:25]([NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH:26]=[CH:27][C:28]=3[CH3:29])[CH2:19][CH2:18]2)=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7023129(2S)-2-(4-chlorophenyl)propanoic acidHCID 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 10051004(2S)-2-(4-chlorophenyl)-N-(3-{4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinyl}propyl)propanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Example 166 was prepared from (2S)-2-(4-chlorophenyl)propanoic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide according to the procedures described in Scheme 12; [α]D=+5.2° (C=1.03, MeOH): 1H NMR (400 MHz, CDCl3) δ 7.55 (d, 1 H, J=2.0 Hz), 7.46 (s, 1 H), 7.34–7.24 (m, 4 H), 7.23–7.17 (m, 1 H), 7.07 (d, 1 H, J=8.0 Hz), 7.04–6.97 (m, 1 H), 3.54 (q, 1 H, J=7.2 Hz), 3.41–3.24 (m, 2 H), 2.95 (ABq, 2 H), 2.72–2.59 (m, 1 H), 2.57–2.45 (m, 1 H), 2.42–2.37 (m, 2 H), 2.27 (s, 3 H), 2.05–1.91 (m, 2 H), 1.82–1.55 (m, 6 H), 1.50 (d, 3 H, J=6.8 Hz), 1.22 (d, 6 H, J=6.8 Hz); ESMS m/e: 484.3 (M+H)+.

Sources & evidence

ORD record
ord-a3d2d4c47c2b41d593cb6d7c42f88ccc
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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