Sodium Bicarbonate → HCID 86761813, compound

HRID 1477276Notes

Reaction equation

HRID 1477276 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C:13]([CH3:40])([CH3:39])[C:14]([N:16]([C:18]2[C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])=[CH:20][C:21]([N:25]3[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]3)=[N+:22]([O-:24])[CH:23]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C([O-])(O)=[O:44].[Na+].OS([O-])(=O)=O.OS(O[O-])(=O)=O.OS(O[O-])(=O)=O.[O-]S([O-])(=O)=O.[K+].[K+].[K+].[K+].[K+]>CO.O>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:40])[C:14]([N:16]([C:18]2[C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])=[CH:20][C:21]([N:25]3[CH2:26][CH2:27][N+:28]([O-:44])([CH3:31])[CH2:29][CH2:30]3)=[N+:22]([O-:24])[CH:23]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 15793144Potassium caroateHCID 86761812HCID 86761812, compound

Product 1

HCID 86761813HCID 86761813, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(2-(3,5-bis(trifluoromethyl)phenyl)-N,2-dimethylpropanamido)-2-(4-methylpiperazin-1-yl)-4-(o-tolyl)pyridine 1-oxide (3 g, 5.05 mmol) and NaHCO3 (0.354 g, 12.66 mmol) in 60 mL of MeOH and 15 mL of H2O were added potassium monopersulfate triple salt (1.62 g, 26.25 mmol) at room temperature during 15 min. After stirring for 4 hrs at room temperature under N2 atmosphere, the reaction mixture was concentrated in vacuo and purified by flash chromatography (eluent: MeOH). The product was dissolved into DCM, the formed solid was filtered off, and the solution was concentrated under reduced pressure to afford 1.77 g 4-(5-(2-(3,5-bis(trifluoromethyl)phenyl)-N,2-dimethylpropanamido)-1-oxido-4-(o-tolyl)pyridin-2-yl)-1-methylpiperazine 1-oxide as a white solid (Yield: 57.4%). 1HNMR (CDCl3, 400 MHz) δ 8.06 (s, 1H), 7.78 (s, 1H), 7.60 (s, 2H), 7.37˜7.20 (m, 4H), 6.81 (s, 1H), 3.89 (s, 21H), 3.74 (m, 4H), 3.31 (m, 5H), 2.48 (s, 3H), 2.18 (s, 3H), 1.36 (s, 6H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (eluent: MeOH)
  3. dissolutionThe product was dissolved into DCM
  4. filtrationthe formed solid was filtered off
  5. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5f676a4023b046fa95c7b3309bdd7f03
Source dataset
uspto-grants-2016_08
Patent number
US09403772B2

Reaction notes

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