Sodium Hydroxide → N-[5-[4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide

HRID 520621Notes

Reaction equation

HRID 520621 reaction equation
[OH-].[Na+].[CH3:3][C@H:4]1[O:9][C@@H:8]([CH3:10])[CH2:7][N:6]([CH2:11][C:12]2[O:16][C:15]([C:17]3[CH:25]=[C:24]([C:26]4[CH:27]=[C:28]([NH:34][S:35]([C:38]5[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:39]=5[F:45])(=[O:37])=[O:36])[C:29]([O:32][CH3:33])=[N:30][CH:31]=4)[CH:23]=[C:22]4[C:18]=3[CH:19]=[N:20][N:21]4S(C3C=CC=CC=3)(=O)=O)=[N:14][N:13]=2)[CH2:5]1>O1CCOCC1>[CH3:10][C@H:8]1[O:9][C@@H:4]([CH3:3])[CH2:5][N:6]([CH2:11][C:12]2[O:16][C:15]([C:17]3[CH:25]=[C:24]([C:26]4[CH:27]=[C:28]([NH:34][S:35]([C:38]5[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:39]=5[F:45])(=[O:36])=[O:37])[C:29]([O:32][CH3:33])=[N:30][CH:31]=4)[CH:23]=[C:22]4[C:18]=3[CH:19]=[N:20][NH:21]4)=[N:14][N:13]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66691781N-[5-[4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide

Product 1

HCID 66695718N-[5-[4-(5-{[(2R,6S)-2,6-Dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamideYield 7.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydroxide (2 ml, 4.00 mmol) was added to a solution of N-[5-[4-(5-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3,4-oxadiazol-2-yl)-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (194 mg, 0.212 mmol) in 1,4-dioxane (2 ml). The mixture was stirred at room temperature for 2 h. The solvent was evaporated under a stream of nitrogen and the residue partitioned between ethyl acetate (10 ml) and saturated ammonium chloride (5 ml). The organic layer was separated by hydrophobic frit, washed with water and the solvent removed in vacuo. The residual solid was purified by Mass Directed Automated Preparative HPLC (Method B) and the solvent was evaporated under a stream of nitrogen to give the title compound as a cream coloured solid (10 mg).

Workup

  1. customThe solvent was evaporated under a stream of nitrogen
  2. customthe residue partitioned between ethyl acetate (10 ml) and saturated ammonium chloride (5 ml)
  3. customThe organic layer was separated by hydrophobic frit
  4. washwashed with water
  5. customthe solvent removed in vacuo
  6. customThe residual solid was purified by Mass Directed Automated Preparative HPLC (Method B)
  7. customthe solvent was evaporated under a stream of nitrogen

Sources & evidence

ORD record
ord-631e045db3db4c35a22a8e019996f072
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

Loading…