1-(2,4-Dichlorophenyl)cyclopropanecarboxylic acid → N-[3-(4-{3-[(cyclopropylcarbonyl)amino]phenyl}-1-piperidinyl)propyl]-1-(2,4-dichlorophenyl)cyclopropanecarboxamide

HRID 2213484Notes

Reaction equation

HRID 2213484 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([OH:14])=O)[CH2:11][CH2:10]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:31][C:32]([CH:34]3[CH2:36][CH2:35]3)=[O:33])[CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20]1>>[CH:34]1([C:32]([NH:31][C:27]2[CH:26]=[C:25]([CH:22]3[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][NH:15][C:12]([C:9]4([C:3]5[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=5[Cl:1])[CH2:10][CH2:11]4)=[O:14])[CH2:24][CH2:23]3)[CH:30]=[CH:29][CH:28]=2)=[O:33])[CH2:35][CH2:36]1

Participants

3

Reactant 2

HCID 7361031-(2,4-Dichlorophenyl)cyclopropanecarboxylic acidHCID 21957166N-{3-[1-(3-aminopropyl)4-piperidinyl]phenyl}cyclopropanecarboxamide

Product 1

HCID 21957259N-[3-(4-{3-[(cyclopropylcarbonyl)amino]phenyl}-1-piperidinyl)propyl]-1-(2,4-dichlorophenyl)cyclopropanecarboxamide

Procedure

Example 117 was prepared from 1-(2,4-dichlorophenyl)cyclopropanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}cyclopropanecarboxamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 8.00–7.82 (br, 1H), 7.52–7.04 (m, 6H), 6.86 (d, 1H, J=7.2 Hz), 5.92–5.73 (br, 1H), 3.35–3.12 (m, 4H), 2.74–2.58 (m, 2H), 2.58–2.42 (m, 1H), 2.40–2.20 (m, 2H), 2.01–1.61 (m, 7H), 1.15–0.90 (m, 6H), 0.89–0.71 (m, 2H); ESMS m/e: 514.2 (M+H)+.

Sources & evidence

ORD record
ord-97e3241aa3c34f6d9e05683c29f18f5c
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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