1-(p-Chlorophenyl)cyclobutanecarboxylic acid → 1-(4-chlorophenyl)-N-(3-{4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinyl}propyl)cyclobutanecarboxamide

HRID 2213455Notes

Reaction equation

HRID 2213455 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([OH:14])=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:26]=[C:27]([NH:32][C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])[CH:28]=[CH:29][C:30]=2[CH3:31])[CH2:21][CH2:20]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]([NH:15][CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([C:25]4[CH:26]=[C:27]([NH:32][C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])[CH:28]=[CH:29][C:30]=4[CH3:31])[CH2:21][CH2:20]3)=[O:14])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acidHCID 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 219571331-(4-chlorophenyl)-N-(3-{4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinyl}propyl)cyclobutanecarboxamide

Procedure

Example 86 was prepared from 1-(4-chlorophenyl)cyclobutanecarboxylic 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 7.46 (d, 1H, J=1.6 Hz), 7.34 (s, 4H), 7.28–7.23 (m, 2H), 7.10 (d, 1H, J=8.4 Hz), 6.45 (br s, 1H), 3.31 (dd, 2H, J=5.6, 11.6 Hz), 2.95 (d, 2H, J=11.6 Hz), 2.88–2.81 (m, 2H), 2.68 (m, 1H), 2.54–2.44 (m, 3H), 2.33 (t, 2H, J=6.4 Hz), 2.29 (s, 3H), 2.11–1.90 (m, 4H), 1.76–1.63 (m, 6H), 1.26 (d, 6H, J=7.2 Hz) ESMS m/e: 510.3 (M+H)+.

Sources & evidence

ORD record
ord-b4323a17e1c74c318f8b5dc9eb5c74e3
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

Loading…