4-Fluorobenzyl bromide → cis-2-[(4-Chlorobenzenesulfonyl)-(4-fluoro-benzyl)-amino]-cyclohexanecarboxylic acid amide

HRID 7038

Reaction equation

HRID 7038 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([NH2:20])=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([NH2:20])=[O:19])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 69655699cis-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide

Product 1

HCID 69656115cis-2-[(4-Chlorobenzenesulfonyl)-(4-fluoro-benzyl)-amino]-cyclohexanecarboxylic acid amideYield 67%

Procedure

The titled compound (178 mg) was prepared in 67% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide and 1-bromomethyl-4-fluoro-benzene according to the procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.74 (d, 2 H, J=8.0 Hz), 7.60 (d, 2 H, J=8.0 Hz), 7.28 (m, 3 H), 7.05 (m, 2 H), 6.67 (s, 1 H), 4.54 (AB2,2 H,Δv=17,Jab=57 Hz), 3.87 (m, 1 H), 2.76 (m, 1 H), 2.45 (m, 1 H), 1.47 (m, 6 H), 0.97 (m, 1 H); MS m/e 425.02 (M+H)+.

Sources & evidence

ORD record
ord-7d9b6a42ebc047d0a4e928f40c44ea67
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Linked notes

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