Potassium Carbonate → HCID 60197192, compound

HRID 877974Notes

Reaction equation

HRID 877974 reaction equation
[CH3:1][N:2]([C:19]1[CH:20]=[N:21][C:22]([N:32](C)[C:33](=O)C(F)(F)F)=[CH:23][C:24]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])[C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][N:2]([C:19]1[CH:20]=[N:21][C:22]([NH:32][CH3:33])=[CH:23][C:24]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])[C:3](=[O:18])[C:4]1[CH:5]=[C:6]([C:14]([F:16])([F:17])[F:15])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86670686HCID 86670686, compound

Product 1

HCID 60197192HCID 60197192, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Methyl-N-(4-o-tolyl-6-(2,2,2-trifluoro-N-methylacetamido)pyridin-3-yl)-3,5-bis (trifluoromethyl)benzamide (70 mg, 0.12 mmol) was stirred in CH3OH (1.5 mL) with potassium carbonate (75 mg, 0.54 mmol) for 1 h. The reaction mixture was then filtered and all volatiles removed under reduced pressure. The residue was dissolved in EtOAc and washed twice with water and twice with brine. The aqueous phases were back-extracted twice with EtOAc and washed with brine. The combined organic layers were dried over Na2SO4. Filtration followed by removal of volatiles under reduced pressure gave a waxy residue. N-Methyl-N-(6-methylamino-4-o-tolyl-pyridin-3-yl)-3,5-bis-trifluoromethyl-benzamide was isolated from this residue by flash chromatography on silica gel (50-67% EtOAc in n-hexane) as a white foam (40 mg, 69%). MS (ESI): m/z=468.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customall volatiles removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed twice with water and twice with brine
  5. extractionThe aqueous phases were back-extracted twice with EtOAc
  6. washwashed with brine
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationFiltration
  9. customfollowed by removal of volatiles under reduced pressure
  10. customgave a waxy residue

Sources & evidence

ORD record
ord-36d87548a9c748e7bf52e10a6d1e3786
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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