(2S)-2-(4-Fluorophenyl)propanoic acid → HCID 16756185, compound

HRID 1269334Notes

Reaction equation

HRID 1269334 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 6950752(2S)-2-(4-Fluorophenyl)propanoic acidHCID 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 16756185HCID 16756185, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Example 168 was prepared from (2S)-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=+13.5° (C=1.02, MeOH): 1H NMR (400 MHz, CDCl3) δ 7.58–7.49 (m, 2 H), 7.37–7.29 (m, 2 H), 7.26–7.19 (m, 1 H), 7.06 (d, 1 H, J=8.0 Hz), 7.04–6.92 (m, 3 H), 3.56 (t, 1 H, J=6.8 Hz), 3.43–3.23 (m, 2 H), 2.95 (ABq, 2 H), 2.63–2.59 (m, 1 H), 2.59–2.45 (m, 1 H), 2.37 (t, 2 H, J=6.0 Hz), 2.27 (s, 3 H), 2.07–1.90 (m, 2 H), 1.82–1.57 (m, 6 H), 1.50 (d, 3 H, J=7.2 Hz), 1.22 (d, 6 H, J=7.2 Hz); ESMS m/e: 468.3 (M+H)+.

Sources & evidence

ORD record
ord-05bfe690839845bd9e13906eea08e573
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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