Cesium carbonate → 4-chloro-N-(trans-2-(hydroxymethyl)cyclopentyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide

HRID 1011507Notes

Reaction equation

HRID 1011507 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[O:34][CH:35]=[CH:36][N:37]=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>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@@H:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:17][OH:18])[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]3[O:34][CH:35]=[CH:36][N:37]=3)=[CH:31][CH:32]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 210755772-(4-(Bromomethyl)phenyl)oxazoleHCID 59497772HCID 59497772, compoundHCID 594977994-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamide

Product 1

HCID 594977794-chloro-N-(trans-2-(hydroxymethyl)cyclopentyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamideYield 80%

Procedure

The title compound was synthesized from 4-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamide (145 mg, 0.5 mmol), cesium carbonate (326 mg, 1.0 mmol), and 2-(4-(bromomethyl)phenyl)oxazole (143 mg, 0.6 mmol) according to the procedure described for 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (Example 2) to give 4-chloro-N-(trans-2-(hydroxymethyl)cyclopentyl)-N-(4-(oxazol-2-yl)benzyl)benzenesulfonamide (178 mg, 80%). 1H NMR (400 MHz, CDCl3) δ ppm 7.99 (2H, d, J=8.31 Hz), 7.66-7.78 (3H, m), 7.43-7.50 (4H, m), 7.22 (1H, s), 4.70 (1H, d, J=16.12 Hz), 4.15 (1H, d, J=16.12 Hz), 3.97-4.08 (1H, m), 3.57 (1H, dd, J=11.58, 4.28 Hz), 3.42 (1H, dd, J=11.46, 3.65 Hz), 1.34-1.71 (8H, m). LC/MS R.T.=2.14 min; [M+H]+=447.12. HRMS [M+H]+ calc'd 447.1145, found 447.1139.

Sources & evidence

ORD record
ord-933cc2d765984e329bb5821c0ba9de8e
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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