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

HRID 1269258Notes

Reaction equation

HRID 1269258 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[CH3:32])[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[CH2:25][CH2:24][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[CH3:32])[CH2:22][CH2:21]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 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 210511361-(4-Chlorophenyl)-N-(3-{4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinyl}propyl)cyclopentanecarboxamide

Procedure

Example 81 was prepared from 1-(4-chlorophenyl)cyclopentanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 7.44 (d, 1H, J=2.0 Hz), 7.37–7.34 (m, 2H), 7.31–7.25 (m, 4H), 7.09 (d, 1H, J=8.0 Hz), 6.50 (brs, 1H), 3.29 (dd, 2H, J=6.4, 12.0 Hz), 2.92 (d, 2H, J=11.6 Hz), 2.66 (m, 1H), 2.54–2.48 (m, 3H), 2.33–2.29 (m, 5H), 2.03–1.94 (m, 4H), 1.83–1.59 (m, 10H), 1.26 (d, 6H, J=6.8 Hz); ESMS m/e: 524.3 (M+H)+.

Sources & evidence

ORD record
ord-99a4d325079649348b02f75ecafb3833
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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