Cesium carbonate → 4-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:18][OH:19])(=[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)=[C:30]([F:39])[C:29]=1[F:40].O1C=NC(C2C=CC(CN([C@@H]3CCCC[C@H]3CO)S(C3C=CC(Cl)=CC=3)(=O)=O)=CC=2)=N1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[O:35][CH:36]=[CH:37][N:38]=3)=[C:30]([F:39])[C:29]=2[F:40])[C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:18][OH:19])(=[O:9])=[O:10])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Procedure
The title compound was synthesized from 4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (200 mg, 0.66 mmol), cesium carbonate (257 mg, 0.79 mmol), and 2-(4-(bromomethyl)-2,3-difluorophenyl)oxazole (217 mg, 0.79 mmol)) according to the procedure described for N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (Example 11) to give 4-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (130 mg, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.35 (s, 1H), 7.83 (d, J=8.50 Hz, 2H), 7.80 (d, J=7.50 Hz, 1H), 7.64 (d, J=8.00 Hz, 2H), 7.45 (t, J=7.05 Hz, 1H), 4.52 (s, 2H), 3.41-3.52 (m, 1H), 3.29-3.40 (m, 1H), 3.25 (dd, J=10.45, 2.64 Hz, 1H), 2.80 (t, J=9.32 Hz, 1H), 1.95 (br. s., 1H), 1.52-1.60 (m, 2H), 1.38 (br. s., 3H), 1.18 (br. s., 1H), 0.86-1.04 (m, 2H). Analytical HPLC R.T.=23.46 min. MS [M+H]+=497; [M+Na]+=519. HRMS [M+H]+ calc'd 497.1113, found 497.1093.
Sources & evidence
- ORD record
- ord-dfa0c1c327374508b41472a07d9fee38
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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