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

HRID 1011516Notes

Reaction equation

HRID 1011516 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][C:29]=1[F:39].O1C=NC(C2C=CC(CN([C@@H]3CCCC[C@H]3CO)S(C3C=CC(Cl)=CC=3)(=O)=O)=CC=2)=N1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[N:38]=[CH:37][O:36][N:35]=3)=[CH:30][C:29]=2[F:39])[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]=1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 576723673-(4-(Bromomethyl)-3-fluorophenyl)-1,2,4-oxadiazoleHCID 594977704-chloro-N-(trans-2-hydroxymethylcyclohexyl)benzenesulfonamideHCID 59497773N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide

Product 1

HCID 594977784-chloro-N-(2-fluoro-4-(1,2,4-oxadiazol-3-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamideYield 24%

Procedure

The title compound was synthesized from 4-chloro-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (200 mg, 0.66 mmol), cesium carbonate (257 mg, 0.79 mmol), and 3-(4-(bromomethyl)-3-fluorophenyl)-1,2,4-oxadiazole (204 mg, 0.79 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 4-chloro-N-(2-fluoro-4-(1,2,4-oxadiazol-3-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamide (75 mg, 24%). 1H NMR (400 MHz, CDCl3) δ ppm 8.77 (s, 1H), 7.91 (dd, J=8.06, 1.51 Hz, 1H), 7.81 (t, J=7.81 Hz, 1H), 7.76 (d, J=10.20 Hz, 1H), 7.74 (d, J=8.60 Hz, 2H), 7.49 (d, J=8.60 Hz, 2H), 4.61 (d, J=15.86 Hz, 1H), 4.40 (d, J=15.61 Hz, 1H), 3.54-3.73 (m, 2H), 3.08 (dd, J=11.96, 1.64 Hz, 1H), 2.64 (br. s., 1H), 1.56-1.78 (m, 3H), 1.49 (ddd, J=12.21, 9.44, 9.32 Hz, 2H), 0.97-1.21 (m, 4H). Analytical HPLC R.T.=23.76 min. MS [M+H]+=480; [M+Na]+=502. HRMS [M+H]+ calcd 480.1160, found 480.1157.

Sources & evidence

ORD record
ord-412f63e704a94ba18783dcfd1734e044
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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