Cesium carbonate → 4-chloro-N-(4-cyano-2,5-difluorobenzyl)-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[C:35]([F:36])=[CH:34][C:31]([C:32]#[N:33])=[C:30]([F:37])[CH:29]=1.ClC1C=CC(S(N(CC2C=CC(C3OC=CN=3)=C(F)C=2F)[C@@H]2CCCC[C@H]2CO)(=O)=O)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:27][C:28]2[CH:29]=[C:30]([F:37])[C:31]([C:32]#[N:33])=[CH:34][C:35]=2[F:36])[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-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (300 mg, 1.0 mmol), cesium carbonate (390 mg, 1.20 mmol), and 4-(bromomethyl)-2,5-difluorobenzonitrile (278 mg, 1.20 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 4-chloro-N-(4-cyano-2,5-difluorobenzyl)-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (350 mg, 77%). 1H NMR (400 MHz, CDCl3) δ ppm 7.74 (m, 2H), 7.59 (dd, J=8.81, 5.79 Hz, 1H), 7.51 (m, 2H), 7.28 (dd, J=8.69, 4.91 Hz, 1H), 4.48 (d, J=15.80 Hz, 1H), 4.39 (d, J=15.80 Hz, 1H), 3.64 (ddd, J=14.00, 9.00, 4.00 Hz, 1H), 3.55 (ddd, J=11.83, 4.78, 3.53 Hz, 1H), 3.16 (ddd, J=11.52, 9.13, 2.27 Hz, 1H), 2.40 (br. s., 1H), 1.68 (d, J=10.58 Hz, 3H), 1.30-1.45 (m, 2H), 0.99-1.21 (m, 4H).
Sources & evidence
- ORD record
- ord-75d2bdca2d404cffaa7daf3369dbfa59
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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