Reaction #7136

ord-474b07b4ecb54a2f8dd335b22ee451cf

Reaction equation

NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1
cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide
COC(=O)c1ccc(CBr)cc1
methyl 4-(bromomethyl)benzoate
→
COC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1
titled compound
Yield 61.0%
COC(=O)c1ccc(CN([C@@H]2CCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1
cis-4-[[(2-Carbamoyl-cyclohexyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-benzoic acid methyl ester
Yield 61.0%

Reactants

NC(=O)[C@@H]1CCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1
cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide
COC(=O)c1ccc(CBr)cc1
methyl 4-(bromomethyl)benzoate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

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)+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084178B2uspto-grants-2006_08