Cesium carbonate → N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-6-(trifluoromethyl)pyridine-3-sulfonamide
Reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][S:10]([C:13]1[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1)(=[O:12])=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[O:38][CH:39]=[CH:40][N:41]=2)=[C:33]([F:42])[C:32]=1[F:43].ClC1C=CC(S(N(CC2C=CC(C3OC=CN=3)=C(F)C=2F)[C@@H]2CCCC[C@H]2CO)(=O)=O)=CC=1>>[F:43][C:32]1[C:33]([F:42])=[C:34]([C:37]2[O:38][CH:39]=[CH:40][N:41]=2)[CH:35]=[CH:36][C:31]=1[CH2:30][N:9]([C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:3]1[CH2:2][OH:1])[S:10]([C:13]1[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1)(=[O:12])=[O:11]Participants
Reactant 4
Product 1
Procedure
The title compound was synthesized from N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-6-(trifluoromethyl)pyridine-3-sulfonamide (50 mg, 0.15 mmol), cesium carbonate (72 mg, 0.22 mmol), and 2-(4-(bromomethyl)-2,3-difluorophenyl)oxazole (50 mg, 0.18 mmol) according to the procedure described for 4-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (Example 20) to give N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-6-(trifluoromethyl)pyridine-3-sulfonamide (41 mg, 52%). 1H NMR (400 MHz, CDCl3) δ ppm 9.07 (d, J=2.01 Hz, 1H), 8.23 (dd, J=8.18, 1.89 Hz, 1H), 7.73-7.84 (m, 3H), 7.44-7.52 (m, 1H), 7.34 (s, 1H), 4.54-4.63 (m, 1H), 4.43-4.53 (m, 1H), 3.77 (td, J=11.58, 3.02 Hz, 1H), 3.60 (dd, J=11.96, 3.15 Hz, 1H), 3.21 (dd, J=11.83, 2.27 Hz, 1H), 3.16 (br. s., 1H), 1.63-1.80 (m, 3H), 1.40-1.61 (m, 2H), 1.35 (dd, J=11.71, 2.14 Hz, 1H), 1.04-1.28 (m, 3H). Analytical HPLC R.T.=22.34 min. HRMS [M+H]+ calc'd 532.1329, found 532.1323.
Sources & evidence
- ORD record
- ord-4aab9682d4824656b8d972d9844ef850
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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