Hydrochloric Acid → HCID 66968619, compound

HRID 2095866Notes

Reaction equation

HRID 2095866 reaction equation
O=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][O:3]1.[F:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([CH3:20])[CH:14]=1.Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O.CN(C)C1C=CN=CC=1>[F:12][C:13]1[CH:19]=[CH:18][C:16]([N:17]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]2=[O:3])=[C:15]([CH3:20])[CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679824-Fluoro-2-methylanilineHCID 117704Methyl 2-oxo-2H-pyran-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 66968619HCID 66968619, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-oxo-2H-pyran-3-carboxylate (3 g, 19.5 mmol) in N,N-dimethylformamide, (18 mL) was added 4-fluoro-2-methylaniline (2.44 g, 19.5 mmol), and the mixture was stirred at room temperature for 3 hr. 4-Dimethylaminopyridine (119 mg, 0.974 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.48 g, 23.4 mmol) were added to the reaction mixture, and the mixture was further stirred at room temperature for 16 hr. 2N Hydrochloric acid was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1), and the obtained solid was washed with hexane/ethyl acetate (=1/1) and collected by filtration to give the title compound (0.40 g, 8%) as a yellow solid.

Workup

  1. stirringthe mixture was further stirred at room temperature for 16 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)
  8. washthe obtained solid was washed with hexane/ethyl acetate (=1/1)
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-aa50eed65663429ba019a91e8310a693
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

Loading…