1-(4-Fluorophenyl)cyclopentanecarboxylic acid → HCID 16756187, compound

HRID 2213461Notes

Reaction equation

HRID 2213461 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[CH3:32])[CH2:22][CH2:21]1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[CH:27]=[C:28]([NH:33][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])[CH:29]=[CH:30][C:31]=4[CH3:32])[CH2:22][CH2:21]3)=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7361331-(4-Fluorophenyl)cyclopentanecarboxylic acidHCID 16757468N-{3-[1-(aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide

Product 1

HCID 16756187HCID 16756187, compound

Procedure

Example 93 was prepared from 1-(4-fluorophenyl)cyclopentanecarboxylic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide according to the procedures described in Scheme 10: 1H NMR (400 MHz, CDCl3) δ 7.43–7.37 (m, 3H), 7.29–7.27 (m, 2H), 7.09 (d, 1H, J=8.4 Hz), 7.04–7.00 (m, 2H), 6.47 (br s, 1H), 3.29 (dd, 2H, J=5.6, 12.0 Hz), 2.94 (d, 2H, J=12.0 Hz), 2.66 (m, 1H), 2.54–2.48 (m, 3H), 2.33–2.30 (m, 2H), 2.29 (s, 3H), 2.03–1.95 (m, 4H), 1.84–1.60 (m, 10H), 1.26 (d, 6H, J=6.8 Hz); ESMS m/e: 508.3 (M+H)+.

Sources & evidence

ORD record
ord-8813a695a1114132a1e997f773ad715f
Source dataset
uspto-grants-2006_09
Patent number
US07105544B2

Reaction notes

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