1-(4-Fluorophenyl)cyclohexane-1-carboxylic acid → N-(3-{4-[2-fluoro-5-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)-1-(4-fluorophenyl)cyclohexanecarboxamide

HRID 1269307Notes

Reaction equation

HRID 1269307 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([OH:16])=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:28]=[C:29]([NH:34][C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])[CH:30]=[CH:31][C:32]=2[F:33])[CH2:23][CH2:22]1>>[F:33][C:32]1[CH:31]=[CH:30][C:29]([NH:34][C:35](=[O:39])[CH:36]([CH3:38])[CH3:37])=[CH:28][C:27]=1[CH:24]1[CH2:23][CH2:22][N:21]([CH2:20][CH2:19][CH2:18][NH:17][C:14]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:16])[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 7361361-(4-Fluorophenyl)cyclohexane-1-carboxylic acidHCID 21957238N-{3-[1-(3-aminopropyl)-4-piperidinyl]4-fluorophenyl}-2-methylpropanamide

Product 1

HCID 21957161N-(3-{4-[2-fluoro-5-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)-1-(4-fluorophenyl)cyclohexanecarboxamide

Procedure

Example 131 was prepared from 1-(4-fluorophenyl)cyclohexanecarboxylic 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 7.49 (s, 1H), 7.43 (dd, 1H, J=6.9, 2.5 Hz), 7.36–7.31 (m, 2H), 7.23–7.17 (m, 1H), 6.93 (t, 2H, J=8.4 Hz), 6.87 (t, 1H, J=8.9 Hz), 6.73–6.68 (m, 1H), 3.21 (q, 2H, J=5.7 Hz), 2.87–2.80 (m, 2H), 2.73–2.65 (m, 1 H), 2.45 (septet, 1H, J=6.7 Hz), 2.30–2.21 (m, 4H), 1.9–1.77 (m, 5H), 1.70–1.63 (m, 3H), 1.56–1.45 (m, 8H), 1.17 (d, 6H, J=6.7 Hz); ESMS m/e: 526.3 (M+H)+.

Sources & evidence

ORD record
ord-6fbb3c3fa5c449d7ae3540993bb07725
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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