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

HRID 1269330Notes

Reaction equation

HRID 1269330 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[C:31]([F:43])=[CH:32][C:33]([F:42])=[C:34]([NH:36][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])[CH:35]=2)[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[CH2:25][CH2:26][CH:27]([C:30]3[C:31]([F:43])=[CH:32][C:33]([F:42])=[C:34]([NH:36][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])[CH:35]=3)[CH2:28][CH2:29]2)=[O:11])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 12068839Bis(4-fluorophenyl)(hydroxy)acetic acidHCID 16757466N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2,4-difluorophenyl}-2-methylpropanamide

Product 1

HCID 18446878N-{5-[1-(3-{[bis(4-fluorophenyl)(hydroxy)acetyl]amino}propyl)-4-piperidinyl]-2,4-difluorophenyl}-2-methylpropanamide

Procedure

Example 160 was prepared from bis(4-fluoro phenyl) (hydroxy)acetic acid and N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2,4-difluoro phenyl}-2-methyl propanamide according to the procedures described in Scheme 12: 1H NMR (400 MHz, CDCl3) δ 9.31 (s, br, 1 H), 8.44–8.33 (m, 1 H), 7.59–7.45 (m, 4 H), 7.39 (s, 1 H), 6.97 (t, 4 H, J=8.8 Hz), 6.80 (t, 1 H, J=9.6 Hz), 5.61–5.36 (br, 1 H), 3.57–3.43 (m, 2 H), 3.14–2.99 (m, 2 H), 2.99–2.84 (m, 1 H), 2.62–2.47 (m, 2 H), 2.47–2.29 (m, 1 H), 2.14–1.93 (m, 4 H), 1.81–1.59 (m, 4 H), 0.98 (apparent t, 6 H, J=6.8 Hz); ESMS m/e: 586.3 (M+H)+.

Sources & evidence

ORD record
ord-374674ae94224652895710b0e29b033b
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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