Cesium carbonate → N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]2[CH2:19][OH:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:39]=[CH:38][O:37][N:36]=2)=[CH:31][CH:30]=1.ClC1C=CC(S(N(CC2C=CC(C#N)=CC=2)[C@@H]2CCCCC[C@H]2CO)(=O)=O)=CC=1>>[O:37]1[CH:38]=[N:39][C:35]([C:32]2[CH:33]=[CH:34][C:29]([CH2:28][N:11]([C@@H:12]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[CH2:19][OH:20])[S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:9])=[O:10])=[CH:30][CH:31]=2)=[N:36]1Participants
Reactant 4
Product 1
Procedure
The title compound was synthesized from 4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (119 mg, 0.38 mmol), cesium carbonate (244 mg, 0.75 mmol), and 3-(4-(bromomethyl)phenyl)-1,2,4-oxadiazole (99 mg, 0.41 mmol) according to the procedure described for 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (Example 40) to give N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (12 mg, 7%). 1H NMR (400 MHz, CDCl3) δ ppm 8.75 (1H, s), 8.05 (2H, d, J=8.56 Hz), 7.68-7.70 (1H, m), 7.66-7.68 (1H, m), 7.47 (2H, d, J=8.56 Hz), 7.43-7.45 (1H, m), 7.41-7.43 (1H, m), 4.67 (1H, d, J=16.62 Hz), 4.44 (1H, d, J=16.62 Hz), 4.23-4.35 (1H, m), 3.60 (1H, dd, J=11.33, 8.56 Hz), 3.35 (1H, dd, J=11.46, 5.41 Hz), 1.99 (1H, br. s.), 1.38-1.81 (6H, m), 1.09-1.32 (5H, LC/MS R.T.=3.09 min; [M+H]+=476.23.
Sources & evidence
- ORD record
- ord-b946bb14e2614cb7a51964e2c6256ebb
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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