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

HRID 1269333Notes

Reaction equation

HRID 1269333 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 7568437(R)-2-(4-chlorophenyl)propanoic acidHCID 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 10254736(2R)-2-(4-chlorophenyl)-N-(3-{4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinyl}propyl)propanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Example 167 was prepared from (2R)-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=−9.3° (C=1.65, MeOH): 1H NMR (400 MHz, CDCl3) δ 7.55 (s, 1 H), 7.36–7.24 (m, 4 H), 7.22–7.12 (m, 2 H), 7.08 (d, 1 H, J=8.0 Hz), 6.92 (s, 1 H), 3.53 (q, 1 H, J=7.2 Hz), 3.42–3.23 (m, 2 H), 2.95 (ABq, 2 H), 2.73–2.59 (m, 1 H), 2.57–2.43 (m, 1 H), 2.42–2.33 (m, 2 H), 2.28 (s, 3 H), 2.08–1.92 (m, 2 H), 1.86–1.56 (m, 6 H), 1.51 (d, 3 H, J=7.2 Hz), 1.24 (d, 6 H, J=6.8 Hz); ESMS m/e: 484.3 (M+H)+.

Sources & evidence

ORD record
ord-98191934e474404683c4ce4a46dd7e33
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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