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

HRID 2213414Notes

Reaction equation

HRID 2213414 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](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20]1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([NH:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32](=[O:36])[CH:33]([CH3:34])[CH3:35])[CH:26]=3)[CH2:21][CH2:20]2)=[O:14])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 7361031-(2,4-Dichlorophenyl)cyclopropanecarboxylic acidHCID 16757470N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}2-methylpropanamide

Product 1

HCID 219571601-(2,4-dichlorophenyl)-N-(3-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}propyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Example 41 was prepared from 1-(2,4-dichlorophenyl)cyclopropanecarboxylic 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 7.67 (s, 1H), 7.49 (s, 1H), 7.44 (d, 1H, J=2.0 Hz), 7.35 (s, 1H), 7.28–7.19 (m, 3H), 6.92 (d, 1H, J=7.6 Hz), 5.69–5.62 (m, 1H), 3.26 (q, 2H, J=6.7 Hz), 2.89–2.82 (m, 2H), 2.54 (quintet, 1H, J=6.7 Hz), 2.47–2.37 (m, 1H), 2.32–2.26 (m, 3H), 1.97–1.88 (m, 2H), 1.79–1.69 (m, 4H), 1.66–1.56 (m, 4H), 1.24 (d, 6H, J=6.7 Hz), 1.05–1.01 (m, 1H); ESMS m/e: 516.2 (M+H)+; Anal. Calc. for C28H35Cl2N3O2.0.048 CHCl3: C, 64.51; H, 6.76; N, 8.05. Found: C, 64.51; H, 6.60; N, 8.15.

Sources & evidence

ORD record
ord-d6ad295ecbff40858ef6e682a8f63c5f
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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