1-(4-Chlorophenyl)cyclohexanecarboxylic acid → 1-(4-chlorophenyl)-N-(3-{4-[6-(isobutyrylamino)-2-pyridinyl]-1-piperidinyl}propyl)cyclohexanecarboxamide

HRID 1269245Notes

Reaction equation

HRID 1269245 reaction equation
[Cl: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[N:32]=[C:31]([NH:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:28]=[CH:29][CH:30]=[C:31]([NH:33][C:34](=[O:38])[CH:35]([CH3:36])[CH3:37])[N:32]=4)[CH2:23][CH2:22]3)=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1008731-(4-Chlorophenyl)cyclohexanecarboxylic acidHCID 21957182N-{6-[1-(3-aminopropyl)-4-piperidinyl]-2-pyridinyl}2-methylpropanamide

Product 1

HCID 219571561-(4-chlorophenyl)-N-(3-{4-[6-(isobutyrylamino)-2-pyridinyl]-1-piperidinyl}propyl)cyclohexanecarboxamide

Procedure

Example 67 was prepared from 1-(4-chlorophenyl)cyclohexanecarboxylic acid and N-{6-[1-(3-aminopropyl)-4-piperidinyl]-2-pyridinyl}-2-methylpropanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.06 (d, 1H, J=8.4 Hz), 7.78 (br s, 1H), 7.65 (t, 1H, J=8.0 Hz), 7.40–7.38 (m, 2H), 7.30–7.27 (m, 2H), 6.88 (d, 2H, J=7.6 Hz), 3.29 (dd, 2H, J=6.0, 11.6 Hz), 2.96 (m, 2H), 2.56–2.49 (m, 2H), 2.36–2.30 (m, 4H), 2.00–1.75 (m, 8H), 1.64–1.59 (m, 8H), 1.25 (d, 6H, J=6.8 Hz); ESMS m/e: 525.3 (M+H)+.

Sources & evidence

ORD record
ord-c4c289d606fd41379cd19d065123ad6d
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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