Potassium Carbonate → HCID 57325410, compound

HRID 2202427Notes

Reaction equation

HRID 2202427 reaction equation
C([C:4]1[CH:9]=[C:8]([N:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[C:12]([Cl:27])[C:11]2=[O:28])[C:7]([CH3:29])=[CH:6][N:5]=1)(=O)C.[C:30](OC(OC(C)(C)C)N(C)C)(C)([CH3:32])[CH3:31].C(=O)([O-])[O-].[K+].[K+].Cl.[OH:51][C:52]([CH3:57])([CH3:56])[C:53]([NH2:55])=[NH:54]>CN(C=O)C>[Cl:27][C:12]1[C:11](=[O:28])[N:10]([C:8]2[C:7]([CH3:29])=[CH:6][N:5]=[C:4]([C:31]3[CH:30]=[CH:32][N:55]=[C:53]([C:52]([OH:51])([CH3:57])[CH3:56])[N:54]=3)[CH:9]=2)[C:15]([CH3:16])=[CH:14][C:13]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[F:26]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 426142842-Hydroxy-2-methylpropanimidamide hydrochlorideHCID 67777241HCID 67777241, compound

Product 1

HCID 57325410HCID 57325410, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2′-acetyl-3-chloro-4-[(2,4-difluorobenzyl)oxy]-5′,6-dimethyl-2H-1,4′-bipyridin-2-one (0.045 g, 0.11 mmol) in DMF (0.5 mL) was added N, N dimethylformamide di-tert-butyl acetal (0.04 g, 0.2 mmol) and heated at 60° C. for 2 h. The reaction mixture was concentrated in vacuo, the residue was treated with toluene (1 mL) and concentrated in vacuo. The resulting residue was dried in vacuo for 2 h, dissolved in DMF (1 mL), and potassium carbonate (0.03 g, 0.22 mmol) and 2-hydroxy-2-methylpropiamidine hydrochloride (0.02 g, 0.14 mmol) were added. This mixture was heated at 80° C. for 12 h under nitrogen and concentrated in vacuo. The residue was partitioned between water (5 mL) and ethyl acetate (15 mL). The organic phase was washed with water, dried with magnesium sulfate, and concentrated. The resulting residue was purified by silica-gel flash chromatography using 3% methanol in ethyl acetate. Appropriate fractions were combined and concentrated under reduced pressure to give 0.022 g of the title compound. ES-MS, m/z=513 (M+H) and 535 (M+Na).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with toluene (1 mL)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was dried in vacuo for 2 h
  5. dissolutiondissolved in DMF (1 mL)
  6. temperatureThis mixture was heated at 80° C. for 12 h under nitrogen
  7. concentrationconcentrated in vacuo
  8. customThe residue was partitioned between water (5 mL) and ethyl acetate (15 mL)
  9. washThe organic phase was washed with water
  10. dry with materialdried with magnesium sulfate
  11. concentrationconcentrated
  12. customThe resulting residue was purified by silica-gel flash chromatography
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14739e9a93484844821b4ca755e882c3
Source dataset
uspto-grants-2016_06
Patent number
US09365547B2

Reaction notes

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