1-(4-Fluorophenyl)cyclopentanecarboxylic acid → HCID 21957242, compound

HRID 2213495Notes

Reaction equation

HRID 2213495 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:27]=[C:28]([NH:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH:29]=[CH:30][C:31]=2[F:32])[CH2:22][CH2:21]1>>[F:32][C:31]1[CH:30]=[CH:29][C:28]([NH:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])=[CH:27][C:26]=1[CH:23]1[CH2:22][CH2:21][N:20]([CH2:19][CH2:18][CH2:17][NH:16][C:13]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10][CH2:11][CH2:12]2)=[O:15])[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 7361331-(4-Fluorophenyl)cyclopentanecarboxylic acidHCID 21957238N-{3-[1-(3-aminopropyl)-4-piperidinyl]4-fluorophenyl}-2-methylpropanamide

Product 1

HCID 21957242HCID 21957242, compound

Procedure

Example 129 was prepared from 1-(4-fluorophenyl)cyclopentanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-fluorophenyl}-2-methylpropanamide according to the procedures described in Scheme 9: 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H), 7.42–7.38 (m, 1H), 7.31–7.20 (m, 2H), 6.94–6.83 (m, 4H), 6.46–6.40 (m, 1H), 3.19 (q, 2H, J=5.6 Hz), 2.85–2.79 (m, 2H), 2.73–2.64 (m, 1H), 2.49–2.38 (m, 3H), 2.22 (t, 2H, J=6.4 Hz), 1.94–1.84 (m, 5H), 1.75–1.47 (m, 9H), 1.17 (d, 6H, J=6.8 Hz); ESMS m/e: 512.3 (M+H)+.

Sources & evidence

ORD record
ord-f3f3c2fd6d7b433dbef66e4fc1afcb28
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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