1-(p-Chlorophenyl)cyclobutanecarboxylic acid → HCID 21957251, compound

HRID 2213444Notes

Reaction equation

HRID 2213444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([OH:14])=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=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:34])[CH3:33])[CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20]1>>[C:32]([NH:31][C:27]1[CH:26]=[C:25]([CH:22]2[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][CH2:16][NH:15][C:12]([C:8]3([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH2:9][CH2:10][CH2:11]3)=[O:14])[CH2:20][CH2:21]2)[CH:30]=[CH:29][CH:28]=1)(=[O:34])[CH3:33]

Participants

3

Reactant 2

HCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acidHCID 21957249N-{3-[1-(3-amino propyl)4-piperidinyl]phenyl}acetamide

Product 1

HCID 21957251HCID 21957251, compound

Procedure

Example 74 was prepared from 1-(4-chlorophenyl)cyclobutanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}acetamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 7.55 (s, 1H), 7.36–7.26 (m, 7H), 6.97 (d, 1H, J=7.2 Hz), 6.50 (br s, 1H), 3.30 (dd, 2H, J=6.0, 12.0 Hz), 2.98–2.95 (m, 2H), 2.87–2.80 (m, 2H), 2.53–2.42 (m, 3H), 2.34 (t, 2H, J=6.4 Hz), 2.20 (s, 3H), 2.15–1.82 (m, 6H), 1.74–0.161 (m, 4H); ESMS m/e: 468.2 (M+H)+.

Sources & evidence

ORD record
ord-ca5b5b5576774a4ca55361fd01fd5db4
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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