Hydrochloric Acid → HCID 86605886, compound

HRID 2221941Notes

Reaction equation

HRID 2221941 reaction equation
[CH:1]([C:3]1[C:4]([O:14][CH2:15][C:16]2[CH:44]=[CH:43][C:19]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:29]=[CH:30][C:31]([O:38]S(C)(=O)=O)=[C:32]([CH:37]=4)[C:33]([O:35][CH3:36])=[O:34])[O:25][C:26]=3[CH3:27])=[C:18]([O:45][CH3:46])[CH:17]=2)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1)=[O:2].[OH-].[Na+].Cl.[C:50](=O)([O-])[O-].[K+].[K+].CI>O.CN(C)C=O.C(O)C.O1CCCC1>[CH:1]([C:3]1[C:4]([O:14][CH2:15][C:16]2[CH:44]=[CH:43][C:19]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:29]=[CH:30][C:31]([O:38][CH3:50])=[C:32]([CH:37]=4)[C:33]([O:35][CH3:36])=[O:34])[O:25][C:26]=3[CH3:27])=[C:18]([O:45][CH3:46])[CH:17]=2)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1)=[O:2]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 86605885HCID 86605885, compound

Product 1

HCID 86605886HCID 86605886, compoundYield 67%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl 5-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-(methanesulfonyloxy)benzoate (0.50 g), tetrahydrofuran (3 mL) and ethanol (3 mL) was added 1N aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at 50° C. for 1 hr. To the reaction mixture were added 1N hydrochloric acid (3 mL) and water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give pale-yellow crystal. A mixture of the crystal, potassium carbonate (0.21 g), methyl iodide (0.55 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give methyl 5-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-methoxybenzoate as pale-yellow crystals (0.30 g, yield 67%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 165-166° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give pale-yellow crystal
  6. stirringwas stirred at room temperature for 3 hrs
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-68095502c1ba4d09a464eebf28d5a16d
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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