Cesium carbonate → HCID 59497814, compound
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
Procedure
The title compound was synthesized from 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (100 mg, 0.32 mmol), cesium carbonate (205 mg, 0.63 mmol), and 3-(4-(bromomethyl)phenyl)-1,2,4-oxadiazole (90 mg, 0.38 mmol) according to the procedure described for 4-Chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (Example 40) to give N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (50 mg, 33%). 1H NMR (400 MHz, CDCl3) δ ppm 8.75 (1H, s), 8.08 (2H, d, J=8.31 Hz), 7.70-7.79 (2H, m), 7.55 (2H, d, J=8.31 Hz), 7.47-7.52 (2H, m), 4.73 (1H, d, J=15.86 Hz), 4.02 (1H, d, J=15.61 Hz), 3.82 (1H, ddd, J=11.14, 8.75, 3.02 Hz), 3.71 (1H, dd, J=11.71, 3.90 Hz), 3.31 (1H, dd, J=11.58, 2.52 Hz), 2.55 (1H, br. s.), 1.43-1.68 (6H, m), 1.17-1.42 (5H, m). LC/MS R.T.=2.29 min; [M+H]+=476.18. HRMS [M+H]+ calc'd 476.1411, found 476.1398.
Sources & evidence
- ORD record
- ord-177ae8ab061f45b4b219d44db7fa450b
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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