1-(p-Chlorophenyl)cyclopropanecarboxylic acid → HCID 21957184, compound

HRID 1269222Notes

Reaction equation

HRID 1269222 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:25]=[C:26]([NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH:27]=[CH:28][CH:29]=2)[CH2:20][CH2:19]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])[CH:25]=4)[CH2:20][CH2:19]3)=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 986061-(p-Chlorophenyl)cyclopropanecarboxylic acidHCID 16757470N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}2-methylpropanamide

Product 1

HCID 21957184HCID 21957184, compound

Procedure

Example 44 was prepared from 1-(4-chlorophenyl)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 7.47 (s, 1H), 7.40 (s, 1H), 7.36–7.30 (m, 5H), 7.27–7.20 (m, 1H), 6.93 (d, 1H, J=7.6 Hz), 5.70–5.63 (m, 1H), 3.24 (q, 2H, J=6.6 Hz), 2.84 (d, 2H, J=11.4 Hz), 2.52 (quintet, 1H, J=7.2 Hz), 2.47–2.37 (m, 1H), 2.26 (t, 2H, J=7.2 Hz), 1.92 (t, 2H, J=11.6 Hz), 1.75 (d, 2H, J=12.5 Hz), 1.65–1.53 (m, 6H), 1.25 (d, 6H, J=7.2 Hz), 1.00 (q, 2H, J=2.9 Hz); ESMS m/e: 482.3 (M+H)+; Anal. Calc. for C28H36ClN3O2.0.540 CH2Cl3: C, 64.93; H, 7.08; N, 7.96. Found: C, 65.00; H, 7.22; N, 7.81.

Sources & evidence

ORD record
ord-1a336f4720844623a2995bfd01acdd0d
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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