Cesium carbonate → HCID 59497795, 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[N:37]=[CH:36][O:35][N:34]=2)=[CH:29][CH:28]=1.O1C=NC(C2C=CC(CN([C@@H]3CCCC[C@H]3CO)S(C3C=CC(Cl)=CC=3)(=O)=O)=CC=2)=N1>>[O:35]1[CH:36]=[N:37][C:33]([C:30]2[CH:31]=[CH:32][C:27]([CH2:26][N:10]([C@@H:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]3[CH2:17][OH:18])[S:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:9])=[O:8])=[CH:28][CH:29]=2)=[N:34]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 mg, 0.39 mmol), and 3-(4-(bromomethyl)phenyl)-1,2,4-oxadiazole (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 N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-5-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)thiophene-2-sulfonamide (20 mg, 13%), 1H NMR (400 MHz, CDCl3) δ ppm 8.75 (s, 1H), 8.07 (m, J=8.31 Hz, 2H), 7.54 (m, J=8.31 Hz, 2H), 7.30 (d, J=4.03 Hz, 1H), 6.91 (d, J=4.03 Hz, 1H), 4.72 (d, J=15.36 Hz, 1H), 4.16 (d, J=15.36 Hz, 1H), 3.60-3.65 (m, 1H), 3.68 (dd, J=11.96, 2.90 Hz, 1H), 3.09 (d, J=12.09 Hz, 1H), 1.70-1.80 (m, 1H), 1.66 (d, J=12.84 Hz, 1H), 1.36-1.61 (m, 4H), 1.12-1.28 (m, 1H), 0.92-1.09 (m, 2H). Analytical HPLC R.T.=21.54 min. MS [M+H]+=468. HRMS [M+H]+ calc'd 468.0819, found 468.0815.
Sources & evidence
- ORD record
- ord-9854291294c5465fa730a2509526c3b7
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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