Cesium carbonate → HCID 59497769, compound
Reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[CH2:17][OH:18])(=[O:9])=[O:8])=[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)=[C:29]([F:38])[C:28]=1[F:39].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[S:6][C:5]([S:7]([N:10]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[O:34][CH:35]=[CH:36][N:37]=3)=[C:29]([F:38])[C:28]=2[F:39])[C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[CH2:17][OH:18])(=[O:9])=[O:8])=[CH:4][CH:3]=1Participants
Procedure
The title compound was synthesized from 5-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)thiophene-2-sulfonamide (100 mg, 0.32 mmol), cesium carbonate (126 mmol, 0.39 mg), and 2-(4-(bromomethyl)-2,3-difluorophenyl)oxazole (93 mg, 0.39 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 5-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)thiophene-2-sulfonamide (28 mg, 17%). 1H NMR (400 MHz, CDCl3) δ ppm 7.78-7.84 (m, 1H), 7.79 (s, 1H), 7.50-7.57 (m, 1H), 7.37 (d, J=4.03 Hz, 1H), 7.32 (s, 1H), 6.95 (d, J=3.78 Hz, 1H), 4.58 (d, J=14.00 Hz, 1H), 4.42 (d, J=14.00 Hz, 1H), 3.53-3.73 (m, 2H), 2.98-3.19 (m, 1H), 2.38 (br. s., 1 H), 1.59-1.84 (m, 3H), 1.40-1.57 (m, 2H), 1.29-1.39 (m, 1H), 1.01-1.26 (m, 3H). Analytical HPLC R.T.=22.41 min. MS [M+H]+=503. HRMS [M+H]+ calc'd 503.0678, found 503.0654.
Sources & evidence
- ORD record
- ord-d17bc4ac330f4bfaa8e0e96c14a45cbd
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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