1-(4-Chlorophenyl)cyclopentanecarboxylic acid → 1-(4-chlorophenyl)-N-(3-{4-[2-fluoro-5-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)cyclopentanecarboxamide

HRID 2213494Notes

Reaction equation

HRID 2213494 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:27]=[C:28]([NH:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH:29]=[CH:30][C:31]=2[F:32])[CH2:22][CH2:21]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH:23]([C:26]4[CH:27]=[C:28]([NH:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH:29]=[CH:30][C:31]=4[F:32])[CH2:24][CH2:25]3)=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 974471-(4-Chlorophenyl)cyclopentanecarboxylic acidHCID 21957238N-{3-[1-(3-aminopropyl)-4-piperidinyl]4-fluorophenyl}-2-methylpropanamide

Product 1

HCID 219572221-(4-chlorophenyl)-N-(3-{4-[2-fluoro-5-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)cyclopentanecarboxamide

Procedure

Example 128 was prepared from 1-(4-chlorophenyl)cyclopentanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-fluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.42–7.38 (m, 1H), 7.27–7.17 (m, 4H), 7.12–7.09 (m, 1H), 6.87 (t, 1H, J=8.6 Hz), 6.49 (t, 1H, J=5.4 Hz), 3.19 (q, 2H, J=5.8 Hz), 2.85–2.79 (m, 2H), 2.73–2.64 (m, 1H), 2.50–2.35 (m, 3H), 2.23 (t, 2H, J=6.6 Hz), 1.92–1.85 (m, 4H), 1.75–1.48 (m, 10H), 1.17 (d, 6H, J=6.7 Hz); ESMS m/e: 528.2 (M+H)+.

Sources & evidence

ORD record
ord-4b3be4ee7302408ebcf0333205bc98d3
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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