Cesium carbonate → N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide

HRID 1011524Notes

Reaction equation

HRID 1011524 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[N:38]=[CH:37][O:36][N:35]=2)=[CH:30][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>>[O:36]1[CH:37]=[N:38][C:34]([C:31]2[CH:32]=[CH:33][C:28]([CH2:27][N:11]([C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[CH2:18][OH:19])[S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:9])=[O:10])=[CH:29][CH:30]=2)=[N:35]1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 594977704-chloro-N-(trans-2-hydroxymethylcyclohexyl)benzenesulfonamideHCID 594977804-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamideHCID 666700193-(4-(Bromomethyl)phenyl)-1,2,4-oxadiazole

Product 1

HCID 59497773N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamideYield 48.1%

Procedure

The title compound was synthesized from 4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (28 mg, 0.09 mmol), cesium carbonate (36 mg, 0.11 mmol), and 3-(4-(bromomethyl)phenyl)-1,2,4-oxadiazole (26 mg, 0.11 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-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (20 mg, 48%). MS [M+H]+=462 HRMS [M+H]+ calc'd 462.1254, found 462.1255. Chiral LC: R.T.=16.21 min., 98.0% ee.

Sources & evidence

ORD record
ord-97f8a74e1ac642d7b534031e05d24125
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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