Cesium carbonate → HCID 59497812, compound

HRID 1011513Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH2:17][OH:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[N:37]=[CH:36][O:35][N:34]=2)=[CH:29][CH:28]=1.ClC1C=CC(S(N(CC2C=CC(C#N)=CC=2)[C@@H]2CCC[C@H]2CO)(=O)=O)=CC=1>>[O:35]1[CH:36]=[N:37][C:33]([C:30]2[CH:31]=[CH:32][C:27]([CH2:26][N:11]([C@@H:12]3[CH2:16][CH2:15][CH2:14][C@@H:13]3[CH2:17][OH:18])[S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:9])=[O:10])=[CH:28][CH:29]=2)=[N:34]1

Participants

Reactant 4

HCID 10796Cesium carbonate

HCID 59497772HCID 59497772, compound

HCID 59497801HCID 59497801, compound

HCID 666700193-(4-(Bromomethyl)phenyl)-1,2,4-oxadiazole

Product 1

HCID 59497812HCID 59497812, compoundYield 13.4%

Procedure

The title compound was synthesized from 4-chloro-N-(cis-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide 145 mg, 0.50 mmol), cesium carbonate (326 mg, 1.0 mmol), and 3-(4-(bromomethyl)phenyl)-1,2,4-oxadiazole (143 mg, 0.60 mmol) according to the procedure described for 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (Example 2) to give N-(4-(1,2,4-oxadiazol-3-yl)benzyl)-4-chloro-N-(cis-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (30 mg, 13%). 1H NMR (400 MHz, CDCl3) δ ppm 8.74 (1H, s), 8.04 (2H, d, J=8.31 Hz), 7.68-7.73 (2H, m), 7.40-7.46 (4H, m), 4.66 (1H, d, J=16.87 Hz), 4.38 (1H, d, J=16.87 Hz), 4.23 (1H, q, J=7.22 Hz), 3.55 (1H, dd, J=11.21, 7.18 Hz), 338 (1H, dd, J=11.33, 5.04 Hz), 2.13-2.28 (1H, m), 1.49-1.83 (5H, m), 1.19-1.29 (1H, m). LC/MS R.T.=2.15 min; [M+H]+=448.14. HRMS [M+H]+ calc'd 448.1098, found 448.1108.

Sources & evidence

ORD record: ord-80e01e73f8c9458bb5659691d45afb30
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977362B2

Reaction notes

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