Sodium hydride → (2-Amino-5-fluoro-4-(3-(4-morpholinyl)propoxy)phenyl)-(2-chlorophenyl)-methanone

HRID 2112487Notes

Reaction equation

HRID 2112487 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8](F)[C:7]([F:11])=[CH:6][C:5]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])=[O:13].[N:21]1([CH2:27][CH2:28][CH2:29][OH:30])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>O1CCOCC1>[NH2:3][C:4]1[CH:9]=[C:8]([O:30][CH2:29][CH2:28][CH2:27][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:7]([F:11])=[CH:6][C:5]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1995763-Morpholino-1-propanolHCID 57642358(2-Amino-4,5-difluorophenyl)(2-chlorophenyl)methanone

Product 1

HCID 57642386(2-Amino-5-fluoro-4-(3-(4-morpholinyl)propoxy)phenyl)-(2-chlorophenyl)-methanoneYield 64.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.4 g (0.035 mole) of 60% sodium hydride, 25 mL of dioxane, 2.68 g (0.01 mole) of (2-amino-4,5-difluorophenyl)-(2-chlorophenyl)-methanone (Xmm) and 2.23 g (0.016 mole) of 4-morpholinepropanol was stirred at room temperature for 4 hours. The mixture was quenched by the addition of 50 mL of water. The mixture was extracted with ethyl acetate, and the extract washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with hexane and then recrystallized from hexane-ethyl acetate to give 2.55 g of (2-amino-5-fluoro-4-(3-(4-morpholinyl)propoxy)phenyl)-(2-chlorophenyl)-methanone (Xi). MH+/Z=393.

Workup

  1. customThe mixture was quenched by the addition of 50 mL of water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with hexane
  8. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-43fd38d3ce984492a62259f130d1bafc
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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