Potassium Carbonate → HCID 90021632, compound

HRID 1487822Notes

Reaction equation

HRID 1487822 reaction equation
Br[CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH3:16])=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:4].Cl.[CH3:19][O:20][CH2:21][C:22](=[NH:24])[NH2:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:19][O:20][CH2:21][C:22]1[NH:23][C:3]([C:5]2[C:6]([CH3:16])=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=2)[C:10]([O:12][CH3:13])=[O:11])=[C:2]([CH3:17])[N:24]=1.[CH3:19][O:20][CH2:21][C:22]1[O:4][C:3]([C:5]2[C:6]([CH3:16])=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=2)[C:10]([O:12][CH3:13])=[O:11])=[C:2]([CH3:17])[N:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 135486022-Methoxyethanimidamide hydrochlorideHCID 90021223HCID 90021223, compound2×

Product 2

HCID 90021632HCID 90021632, compoundYield 52%HCID 178494667HCID 178494667, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Into a 100-mL round-bottom flask, was placed a mixture of methyl 5-(2-bromopropanoyl)-2,4-dimethylbenzoate (compound 1.6, 600 mg, 2.01 mmol), 2-methoxyethanimidamide hydrochloride (510 mg, 4.09 mmol), potassium carbonate (840 mg, 6.08 mmol) and acetonitrile (30 mL). The resulting mixture was stirred at 80° C. overnight, then cooled to room temperature and concentrated under reduced pressure. The residue was diluted with H2O (50 mL) and extracted with ethyl acetate (100 mL). The organics was washed brine (2×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:2) as the eluent to yield methyl 5-(2-(methoxymethyl)-4-methyl-1H-imidazol-5-yl)-2,4-dimethylbenzoate (compound 2.1) (0.11 g, 19%) and methyl 5-(2-(methoxymethyl)-4-methyloxazol-5-yl)-2,4-dimethylbenzoate (compound 2.2) (0.30 g, 52%), both as a yellow oils.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with H2O (50 mL)
  5. extractionextracted with ethyl acetate (100 mL)
  6. washThe organics was washed brine (2×50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:2) as the eluent

Sources & evidence

ORD record
ord-9f74e0ce56e449ccaa18059fe1faa499
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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