4-(Trifluoromethylthio)benzyl bromide → (1S,2R)-2-[(4-Chlorobenzenesulfonyl)-(4-trifluoromethylsulfanyl-benzyl)-amino]-cyclohexanecarboxylic acid amide

HRID 7035

Reaction equation

HRID 7035 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]([S:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1>CO>[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]([S:29][C:30]([F:33])([F:31])[F:32])=[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

4

Reactant 2

HCID 27778824-(Trifluoromethylthio)benzyl bromideHCID 69656354(1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide

Product 1

HCID 11420795(1S,2R)-2-[(4-Chlorobenzenesulfonyl)-(4-trifluoromethylsulfanyl-benzyl)-amino]-cyclohexanecarboxylic acid amideYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The titled compound was prepared in 64% yield from (1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (100 mg, 0.316 mmol) and 1-bromomethyl-4-trifluoromethylsulfanyl-benzene (90 mg, 0.332 mmol) according to the procedure described in Example 3: 1H NMR (400 Mz, DMSO-d6) δ 7.79 (d, 2 H, J=8.8), 7.61 (d, 2 H, J=8.8), 7.59 (d, 2 H), J=8.1), 7.43 (d, 2 H, J=8.1), 7.32 (br s, 1 H), 6.65 (br s, 1 H), 4.62 (ABq, 2 H, Δv=73.1, Jab=17.3), 3.88 (dt, 1 H, Jd=12.7, Jt=3.9), 2.79 (m, 1 H), 2.43 (m, 1 H), 1.79 (m, 1 H), 1.65 (m, 2 H), 1.42–1.19 (m, 3 H), 0.94 (m, 1 H); MS m/e 529.1 (M+Na)+. Optical rotation: [α]D=−28.6 (c=5.87 mg/mL, MeOH).

Sources & evidence

ORD record
ord-aaa12cfaca7042c7bba0cb2fba7fe154
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Linked notes

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