Water → (3,5-Difluoro-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone

HRID 1943669Notes

Reaction equation

HRID 1943669 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2.[F:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([F:23])[C:20]=1[O:21][CH3:22])[C:15](Cl)=[O:16].C(N(CC)CC)C.O>ClCCl>[F:11][C:12]1[CH:13]=[C:14]([C:15]([N:4]2[CH2:5][CH2:6][O:1][C:2]3[CH:10]=[CH:9][N:8]=[CH:7][C:3]2=3)=[O:16])[CH:18]=[C:19]([F:23])[C:20]=1[O:21][CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 177506623,5-Difluoro-4-methoxybenzoyl chlorideHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 44608224(3,5-Difluoro-4-methoxy-phenyl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanoneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (60 mg, 0.44 mmol) and 3,5-difluoro-4-methoxy-benzoyl chloride (120 mg, 0.572 mmol) were dissolved in dichloromethane (1 ml). Triethylamine (0.080 ml, 0.57 mmol) was added thereto and stirred at room temperature for 1 hour. After completion of the reaction by adding water to the reaction mixture, the organic layer was extracted with dichloromethane, and the combined organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:ethyl acetate:n-hexane=1:2:5. The fractions containing the product were collected and evaporated to obtain the target compound 28 as white solid (102 mg, 76%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe organic layer was extracted with dichloromethane
  3. washthe combined organic layer was washed with water and saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
  8. additionThe fractions containing the product
  9. customwere collected
  10. customevaporated

Sources & evidence

ORD record
ord-72118c3a5d5d4031a09527daba958d42
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

Loading…