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

HRID 1011553Notes

Reaction equation

HRID 1011553 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2([CH2:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)(=[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.BrC1C=CC(CN(C2(CO)CCCCC2)S(C2C=CC(Cl)=CC=2)(=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:12]3([CH2:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[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 210787144-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamideHCID 66669636N-(4-bromobenzyl)-4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamideHCID 666700193-(4-(Bromomethyl)phenyl)-1,2,4-oxadiazole

Product 1

HCID 59497806N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamideYield 9.1%

Procedure

The title compound was synthesized from 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide (114 mg, 0.38 mmol), cesium carbonate (244 mg, 0.75 mmol), and 3-(4-(bromomethyl)phenyl)-1,2,4-oxadiazole (99 mg, 0.41 mmol) according to the procedure described for N-(4-bromobenzyl)-4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide (Example 39) to give N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide (16 mg, 9%). 1H NMR (400 MHz, CDCl3) δ ppm 8.75 (1H, s), 8.08 (2H, d, J=8.31 Hz), 7.80 (2H, d, J=8.56 Hz), 7.39-7.45 (4H, m), 4.38 (2H, d, J=5.79 Hz), 4.08-4.12 (2H, m), 1.68-1.82 (2H, m), 1.29-1.49 (8H, m). LC/MS R.T.=2.93 min; [M+Na]+=484.20.

Sources & evidence

ORD record
ord-9be74044f06245448087ffa771f44b5e
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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