Cesium carbonate → 4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)-N-(4-(oxazol-2-yl)benzyl)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[O:36][CH:37]=[CH:38][N:39]=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>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]2[CH2:19][OH:20])[CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]3[O:36][CH:37]=[CH:38][N:39]=3)=[CH:33][CH:34]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=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 2-(4-(bromomethyl)phenyl)oxazole (98 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 4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide (97 mg, 54%). 1H NMR (400 MHz, CDCl3) δ ppm 7.95 (2H, d, J=8.31 Hz), 7.71 (1H, s), 7.66 (2H, d, J=8.56 Hz), 7.43 (4H, t, J=9.06 Hz), 7.26 (1H, s), 4.64 (1H, d, J=16.62 Hz), 4.41 (1H, d, J=16.62 Hz), 4.24-4.31 (1H, m), 3.57 (1H, dd, J=11.33, 8.31 Hz), 3.33 (1H, dd, J=11.33, 5.54 Hz), 1.90-2.05 (1H, m), 1.40-1.78 (6H, m), 1.11-1.34 (5H, m). LC/MS R.T.=2.21 min; [M+H]+=475.11. HRMS [M+H]+ calc'd 475.1458, found 475.1437.
Sources & evidence
- ORD record
- ord-485e173573214a69aed03dcc12f4b386
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
Loading…