Cesium carbonate → 6-(Trifluoromethyl)pyridine-3-sulfonamide

HRID 1011534Notes

Reaction equation

HRID 1011534 reaction equation
OC[C@@H]1CCCC[C@H]1[NH:9][S:10]([C:13]1[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1)(=[O:12])=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].BrCC1C(F)=CC(C2N=CON=2)=C(F)C=1.ClC1C=CC(S(N(CC2C=CC(C3OC=CN=3)=C(F)C=2F)[C@@H]2CCCC[C@H]2CO)(=O)=O)=CC=1>>[F:22][C:19]([F:20])([F:21])[C:16]1[N:15]=[CH:14][C:13]([S:10]([NH2:9])(=[O:12])=[O:11])=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 594977804-chloro-N-(2,3-difluoro-4-(oxazol-2-yl)benzyl)-N-(trans-2-(hydroxymethyl)cyclohexyl)benzenesulfonamideHCID 59497782N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-6-(trifluoromethyl)pyridine-3-sulfonamideHCID 666700973-(4-(Bromomethyl)-2,5-difluorophenyl)-1,2,4-oxadiazole

Product 1

HCID 592688866-(Trifluoromethyl)pyridine-3-sulfonamideYield 82.5%

Procedure

The title compound was synthesized from N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-6-(trifluoromethyl)pyridine-3-sulfonamide (50 mg, 0.15 mmol), cesium carbonate (72 mg, 0.22 mmol), and 3-(4-(bromomethyl)-2,5-difluorophenyl)-1,2,4-oxadiazole (50 mg, 0.18 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-(2,5-difluoro-4-(1,2,4-oxadiazol-3-yl)benzyl)-N-(1R,2R)-2-(hydroxymethyl)cyclohexyl)-6-(trifluoromethyl)pyridine-3-sulfonamide (28 mg, 35%). 1H NMR (400 MHz, CDCl3) δ ppm 9.08 (d, J=2.01 Hz, 1H), 8.82 (s, 1H), 8.25 (dd, J=8.31, 2.01 Hz, 1H), 7.81 (d, J=8.31 Hz, 1H), 7.74 (dd, J=9.82, 5.54 Hz, 1H), 7.55 (dd, J=10.20, 5.92 Hz, 1H), 4.53 (d, J=15.50 Hz, 1H), 4.47 (d, J=15.60 Hz, 1H), 3.70-3.84 (m, 1H), 3.57 (dd, J=11.71, 2.90 Hz, 1H), 321 (d, J=11.58 Hz, 1H), 1.63-1.81 (m, 3H), 1.43-1.56 (m, 2H), 1.33-1.41 (m, 1H), 1.16-1.31 (m, 2H), 1.05-1.14 (m, 1H). Analytical HPLC R.T=21.66. HRMS [M+H]+ calc'd 533.1282, found 533.1277.

Sources & evidence

ORD record
ord-319da20a0cab426aa01101962e1b23b7
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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