Bis(4-fluorophenyl)(hydroxy)acetic acid → N-{3-[1-(3-{[bis(4-fluorophenyl)(hydroxy)acetyl]amino}propyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

HRID 1269326Notes

Reaction equation

HRID 1269326 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)([OH:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:31]=[C:32]([NH:37][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])[CH:33]=[CH:34][C:35]=2[CH3:36])[CH2:26][CH2:25]1>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)([OH:12])[C:9]([NH:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([C:30]3[CH:31]=[C:32]([NH:37][C:38](=[O:42])[CH:39]([CH3:40])[CH3:41])[CH:33]=[CH:34][C:35]=3[CH3:36])[CH2:26][CH2:25]2)=[O:11])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 12068839Bis(4-fluorophenyl)(hydroxy)acetic acidHCID 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 10076577N-{3-[1-(3-{[bis(4-fluorophenyl)(hydroxy)acetyl]amino}propyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Procedure

Example 156 was prepared from bis(4-fluorophenyl)(hydroxy)acetic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide according to the procedures described in Scheme 12: 1H NMR (400 MHz, CDCl3) δ 9.44 (s, br, 1 H), 8.18 (s, 1 H), 7.62–7.48 (m, 4 H), 7.32 (s, 1 H), 7.07–7.00 (m, 1 H), 7.00–6.89 (m, 4 H), 6.72–6.53 (m, 1 H), 5.96–5.71 (br, 1 H), 3.55–3.44 (m, 2 H), 3.14–3.02 (m, 2 H), 2.83–2.66 (m, 1 H), 2.63–2.49 (m, 2 H), 2.39–2.22 (m, 1 H), 2.29 (s, 3 H), 2.17–1.98 (m, 4 H), 1.78–1.59 (m, 4 H), 0.92 (d, 6 H, J=6.8 Hz); ESMS m/e: 564.4 (M+H)+.

Sources & evidence

ORD record
ord-7bcb09c3efe44f65bb05e9e77a60e566
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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