Cesium carbonate → 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)-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:12]2([CH2:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[O:35][CH:36]=[CH:37][N:38]=2)=[CH:30][CH:29]=1.BrC1C=CC(CN(C2(CO)CCCCC2)S(C2C=CC(Cl)=CC=2)(=O)=O)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:12]2([CH2:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]3[O:35][CH:36]=[CH:37][N:38]=3)=[CH:32][CH:33]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Procedure
The title compound was synthesized from 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide (114 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 N-(4-bromobenzyl)-4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide (Example 39) to give 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide (145 mg, 84%). 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (2H, d, J=8.06 Hz), 7.77 (2H, d, J=8.56 Hz), 7.69 (1H, s), 7.45 (4H, dd, J=15.36, 8.56 Hz), 7.21 (1H, s), 4.78 (2H, s), 3.86 (2H, br. s.), 2.92 (1H, hr. s.), 1.81-1.90 (2H, m), 1.42-1.54 (5H, m), 1.20-1.31 (2H, m), 0.95-1.07 (1H, m). LC/MS R.T.=2.18 min; [M+H]+=461.08. HRMS [M+H]+ calc'd 461.1302, found 461.1321.
Sources & evidence
- ORD record
- ord-ca777017bf944c97bb6beffdd9e231cf
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
Loading…