Cesium carbonate → 4-chloro-N-(cis-2-(hydroxymethyl)cyclopentyl)-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[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH2:17][OH:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[O:34][CH:35]=[CH:36][N:37]=2)=[CH:29][CH:28]=1.ClC1C=CC(S(N(CC2C=CC(C#N)=CC=2)[C@@H]2CCC[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[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH2:17][OH:18])[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]3[O:34][CH:35]=[CH:36][N:37]=3)=[CH:31][CH:32]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1Participants
Procedure
The title compound was synthesized from 4-chloro-N-(cis-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide 145 mg, 0.50 mmol), cesium carbonate (326 mg, 1.0 mmol), and 2-(4-(bromomethyl)phenyl)oxazole (143 mg, 0.60 mmol) according to the procedure described for 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (Example 2) to give 4-chloro-N-(cis-2-(hydroxymethyl)cyclopentyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide (117 mg, 52%). 1H NMR (400 MHz, CDCl3) δ ppm 7.94 (2H, d, J=8.31 Hz), 7.63-7.69 (3H, m), 7.33-7.44 (4H, m), 7.19 (1H, s), 4.62 (1H, d, J=16.62 Hz), 4.34 (1H, d, J=16.87 Hz), 4.19 (1H, q, J=7.47 Hz), 3.52 (1H, dd, J=11.21, 6.92 Hz), 3.33 (1H, dd, J=11.33, 5.54 Hz), 2.37-2.63 (1H, m), 2.09-2.25 (1H, m), 1.38-1.74 (5H, m), 1.15-1.30 (1H, m). LC/MS R.T.=2.76 min; [M+H]+=447.20. HRMS [M+H]+ calc'd 447.1145, found 447.1137.
Sources & evidence
- ORD record
- ord-a97d736a588f4251b4230cf314d16616
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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