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

HRID 1269335Notes

Reaction equation

HRID 1269335 reaction equation
[F: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>[F: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 7005040(R)-2-(4-fluorophenyl)propanoic acidHCID 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 16756186(2R)-2-(4-fluorophenyl)-N-(3-{4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinyl}propyl)propanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Example 169 was prepared from (2R)-2-(4-fluorophenyl)propanoic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide according to the procedures described in Scheme 12; [α]D=−9.1° (C=1.65, MeOH): 1H NMR (400 MHz, CDCl3) δ 7.51 (d, 1 H, J=2.0 Hz), 7.37–7.28 (m, 2 H), 7.23–7.14 (m, 2 H), 7.08 (d, 1 H, J=8.0 Hz), 7.05–6.96 (m, 2 H), 6.90–6.82 (m, 1 H), 3.54 (q, 1 H, J=7.2 Hz), 3.43–3.23 (m, 2 H), 2.95 (ABq, 2 H), 2.73–2.59 (m, 1 H), 2.57–2.42 (m, 1 H), 2.42–2.32 (m, 2 H), 2.28 (s, 3 H), 2.07–1.91 (m, 2 H), 1.83–1.57 (m, 6 H), 1.51 (d, 3 H, J=7.2 Hz), 1.23 (d, 6 H, J=6.8 Hz); ESMS m/e: 468.3 (M+H)+.

Sources & evidence

ORD record
ord-874fb9f13c864bc88e03369b1991759c
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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