2,2-Bis(4-fluorophenyl)acetic acid → N-{3-[1-(3-{[2,2-bis(4-fluorophenyl)acetyl]amino}propyl)-4-piperidinyl]phenyl}butanamide

HRID 1269205Notes

Reaction equation

HRID 1269205 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:30]=[C:31]([NH:35][C:36](=[O:40])[CH2:37][CH2:38][CH3:39])[CH:32]=[CH:33][CH:34]=2)[CH2:25][CH2:24]1>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([NH:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[CH:30]=[C:31]([NH:35][C:36](=[O:40])[CH2:37][CH2:38][CH3:39])[CH:32]=[CH:33][CH:34]=3)[CH2:25][CH2:24]2)=[O:11])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 135116842,2-Bis(4-fluorophenyl)acetic acidHCID 21957120N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}butanamide

Product 1

HCID 21957154N-{3-[1-(3-{[2,2-bis(4-fluorophenyl)acetyl]amino}propyl)-4-piperidinyl]phenyl}butanamide

Procedure

Example 27 was prepared from bis(4-fluorophenyl) acetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}butanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 7.69 (t, 1H, J=5.2 Hz), 7.52 (s, 1H), 7.38 (d, 1H, J=8.0 Hz), 7.30–7.27 (m, 4H), 7.20 (t, 1H, J=8.0 Hz), 7.00–6.95 (m, 4H), 6.89 (d, 1H, J=8.0 Hz), 4.90 (s, 1H), 3.37 (dd, 2H, J=6.0, 11.6 Hz), 3.05 (d, 2H, J=11.2 Hz), 2.55 (t, 2H, J=6.8 Hz), 2.49 (m, 1H), 2.33 (t, 2H, J=7.2 Hz), 2.17 (m, 2H), 1.79–1.69 (m, 8H), 0.97 (t, 3H, J=7.6 Hz); ESMS m/e: 534.4 (M+H)+.

Sources & evidence

ORD record
ord-e9e6d091f7ab4cd8b797497584589b2f
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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