1-(Bromomethyl)-4-(trifluoromethyl)benzene → cis-2-[(4-Chlorobenzenesulfonyl)-(4-trifluoromethyl-benzyl)-amino]-cyclopentanecarboxylic acid amide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[C:17]([NH2:19])=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=2)[C@H:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[C:17]([NH2:19])=[O:18])(=[O:9])=[O:10])=[CH:4][CH:3]=1Participants
3
Procedure
The titled compound (191 mg) was prepared in 50% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclopentanecarboxylic acid amide (250 mg, 0.83 mmol) and 1-bromomethyl-4-trifluoromethyl-benzene according to the N-alkylation procedure described in Example 11: 1 H NMR (DMSO-d6) δ 7.73 (d, 2 H, J=8.0 Hz), 7.56 (m, 4 H), 7.41 (d, 2 H, J=8.0 Hz), 7.08 (s br, 1 H), 6.77 (s br, 1 H), 4.66 (AB2,2 H,Δv=20,Jab=24 Hz), 4.37 (m, 1 H), 2.85 (m, 1 H), 1.76 (m, 4 H), 1.51 (m, 2 H); MS m/e 460.98 (M+H)+.