Methyl 4-(bromomethyl)benzoate → cis-4-[[(2-Carbamoyl-cyclohexyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-benzoic acid methyl ester

HRID 7040

Reaction equation

HRID 7040 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:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1>>[CH3:30][O:29][C:27](=[O:28])[C:26]1[CH:31]=[CH:32][C:23]([CH2:22][N:11]([C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]2[C:18](=[O:19])[NH2:20])[S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 69655699cis-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide

Product 1

HCID 11202122cis-4-[[(2-Carbamoyl-cyclohexyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-benzoic acid methyl esterYield 61%

Procedure

The titled compound (90 mg) was prepared in 61% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide and methyl 4-(bromomethyl)benzoate according to the procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.83 (m, 4 H), 7.64 (d, 2 H, J=8.0 Hz), 7.42 (d, 2 H,J=8.0 Hz), 7.28 (s, 1 H), 6.61 (s, 1 H), 4.64 (AB2,2 H,Δv=20,Jab=72 Hz), 3.85 (m, 4 H), 2.79 (m, 1 H), 2.42 (m, 1 H), 1.78 (m, 1 H), 1.63 (m, 2 H), 1.28 (m, 3 H), 0.90 (m, 1 H); MS m/e 464.98 (M+H)+.

Sources & evidence

ORD record
ord-474b07b4ecb54a2f8dd335b22ee451cf
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Linked notes

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