Water → HCID 57340967, compound

HRID 1025290Notes

Reaction equation

HRID 1025290 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][C:4]1=[O:9].Cl[CH2:11][CH2:12][O:13][C:14]1[CH:18]=[C:17]([CH3:19])[N:16]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[N:15]=1.O>CN(C=O)C>[CH3:19][C:17]1[N:16]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[N:15]=[C:14]([O:13][CH2:12][CH2:11][N:3]2[CH2:8][CH2:7][O:6][CH2:5][C:4]2=[O:9])[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 67773124HCID 67773124, compound

Product 1

HCID 57340967HCID 57340967, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
2.5 °C

Procedure

To a stirred suspension of sodium hydride (65 mg 60% dispersion in mineral oil, 1.63 mmol) in DMF (3 ml), cooled to 0-5° C., a solution of morpholin-3-one (91 mg, 0.91 mmol) in DMF (3 ml) was added dropwise. The mixture was stirred at room temperature for 3 hrs. Then, a solution of 3-(2-chloroethoxy)-5-methyl-1-(naphthalen-2-yl)-1H-pyrazole (200 mg, 0.7 mmol) in DMF (4 ml) was added and the mixture was heated to 50° C. for 14 hrs. The reaction mixture was cooled, water (2 ml) added dropwise, and it was evaporated to dryness in vacuum. The resulting residue was partitioned between dichloromethane and water. The organic layer was washed with water, dried over Na2SO4, filtered and evaporated giving 223 mg of crude residue, which was purified by a silica gel column chromatography (eluent: ethyl acetate) and 4-(2-(5-methyl-1-(naphthalen-2-yl)-1H-pyrazol-3-yloxy)ethyl)morpholin-3-one (192 mg, 78%) was obtained as an amorphous white solid.

Workup

  1. temperaturethe mixture was heated to 50° C. for 14 hrs
  2. temperatureThe reaction mixture was cooled
  3. customit was evaporated to dryness in vacuum
  4. customThe resulting residue was partitioned between dichloromethane and water
  5. washThe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customgiving 223 mg of crude residue, which
  10. customwas purified by a silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-4af0d08b73784b498597cadeafd9af60
Source dataset
uspto-grants-2014_05
Patent number
US08729073B2

Reaction notes

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