2,2-Bis(4-fluorophenyl)acetic acid → N-{5-[1-(3-{[Bis(4-fluorophenyl)acetyl]amino}propyl)-4-piperidinyl]-2-fluorophenyl)butanamide

HRID 2213471Notes

Reaction equation

HRID 2213471 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]=[CH:31][C:32]([F:41])=[C:33]([NH:35][C:36](=[O:40])[CH2:37][CH2:38][CH3:39])[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[CH2:24][CH2:25][CH:26]([C:29]3[CH:30]=[CH:31][C:32]([F:41])=[C:33]([NH:35][C:36](=[O:40])[CH2:37][CH2:38][CH3:39])[CH:34]=3)[CH2:27][CH2:28]2)=[O:11])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 135116842,2-Bis(4-fluorophenyl)acetic acidHCID 21957132N-{5-[1-(3-aminopropyl)4-piperidinyl]-2-fluorophenyl}butanamide

Product 1

HCID 21957148N-{5-[1-(3-{[Bis(4-fluorophenyl)acetyl]amino}propyl)-4-piperidinyl]-2-fluorophenyl)butanamide

Procedure

Example 104 was prepared from bis(4-fluorophenyl)acetic acid and N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2-fluorophenyl}butanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.33–8.14 (m, 1H), 7.89–7.67 (br, 1H), 7.51–6.60 (m, 10H), 4.98–4.79 (br, 1H), 4.75 (s, 1H), 3.46–3.29 (m, 2H), 3.29–3.08 (m, 2H), 2.79–2.63 (m, 2H), 2.63–2.46 (m, 1H), 2.46–2.21 (m, 4H), 1.97–1.60 (m, 8H), 1.01 (t, 3H, J=7.2 Hz); ESMS m/e: 552.3 (M+H)+.

Sources & evidence

ORD record
ord-99af5015c7cd4e7da4e2a4ed82659cf4
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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