Reaktion #7142

ord-6b5454ca797445e19ec258975c3d6f82

Reaktionsgleichung

NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1
cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide
FC(F)(F)c1ccc(CBr)cc1
1-bromomethyl-4-trifluoromethyl-benzene
→
NC(=O)[C@@H]1CCCCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1
titled compound
Ausbeute 58.0%
NC(=O)[C@@H]1CCCCC[C@@H]1N(Cc1ccc(C(F)(F)F)cc1)S(=O)(=O)c1ccc(Cl)cc1
cis-2-[(4-Chlorobenzenesulfonyl)-(4-trifluoromethyl-benzyl)-amino]-cycloheptanecarboxylic acid amide
Ausbeute 58.0%

Edukte

NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1
cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide
FC(F)(F)c1ccc(CBr)cc1
1-bromomethyl-4-trifluoromethyl-benzene

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The titled compound (127 mg) was prepared in 58% yield from cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide (150 mg, 0.45 mmol) and 1-bromomethyl-4-trifluoromethyl-benzene according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.80 (m, 2 H, J=8.0 Hz), 7.62 (m, 4 H), 7.52 (d, 2 H, J=8.0 Hz), 7.35 (s br, 1 H), 6.70 (s br, 1 H), 4.61 (AB2,2 H,Δv=20,Jab=104 Hz), 3.98 (m, 1 H), 2.80 (m, 1 H), 2.29 (m, 1 H), 1.74 (m, 2 H), 1.43 (m, 5 H), 1.22 (m, 2 H); MS m/e 511.05 (M+Na)+.

Quelle

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