1-(2-Chloro-4-fluorophenyl)cyclohexanecarboxylic acid → 1-(2-chloro-4-fluorophenyl)-N-(3-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)cyclohexanecarboxamide

HRID 1269314

Reaction equation

HRID 1269314 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:15]([OH:17])=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[NH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:29]=[C:30]([NH:34][C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])[CH:31]=[CH:32][CH:33]=2)[CH2:24][CH2:23]1>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:15]([NH:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35](=[O:39])[CH:36]([CH3:37])[CH3:38])[CH:29]=3)[CH2:24][CH2:23]2)=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 12681661-(2-Chloro-4-fluorophenyl)cyclohexanecarboxylic acidHCID 16757470N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}2-methylpropanamide

Product 1

HCID 219572701-(2-chloro-4-fluorophenyl)-N-(3-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)cyclohexanecarboxamide

Procedure

Example 138 was prepared from 1-(2-chloro-4-fluorophenyl)cyclohexanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.52–7.46 (m, 1H), 7.45–7.43 (m, 1H), 7.30 (s, 1H), 7.22 (s, 1H), 7.17 (t, 1H, J=7.9 Hz), 7.07–7.01 (m, 2H), 6.89–6.84 (m, 1H), 5.99–5.94 (m, 1H), 3.21 (q, 2H, J=5.7 Hz), 2.87–2.80 (m, 2H), 2.59–2.49 (m, 1H), 2.44 (septet, 1H, J=6.5 Hz), 2.41–2.40 (m, 2H), 2.26 (t, 2H, J=5.7 Hz), 2.04–1.96 (m, 2H), 1.93–1.85 (m, 2H), 1.82–1.71 (m, 4H), 1.64–1.50 (m, 8H), 1.17 (d, 6H, J=6.5 Hz); ESMS m/e: 542.1 (M+H)+.

Sources & evidence

ORD record
ord-b48c1845d0cd4bb1a873a0d82ee96ddc
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Linked notes

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