Hydrochloric Acid → (2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-(3-fluoro-4-methoxy-phenyl)-methanone

HRID 1943665Notes

Reaction equation

HRID 1943665 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]=[CH:19][C:20]=1[O:21][CH3:22])[C:15](Cl)=[O:16].C(N(CC)CC)C.Cl>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([C:15]([C:14]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:12]([F:11])[CH:13]=2)=[O:16])[C:3]2[CH:7]=[N:8][CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27792553-Fluoro-4-methoxybenzoyl chlorideHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 66936494(2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-(3-fluoro-4-methoxy-phenyl)-methanoneYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (50 mg, 0.441 mmol) and 3-fluoro-4-methoxy-benzoyl chloride (125 mg, 0.661 mmol) were dissolved in dichloromethane. Triethylamine (0.77 ml, 1.288 mmol) was added thereto and then stirred at room temperature for 2 hours. After neutralizing with 1N hydrochloric acid solution, the mixture was extracted with dichloromethane and the combined organic layer was 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 ethyl acetate. The fractions containing the product were collected and evaporated to obtain white solid (42.1 mg, 33%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with a solvent of ethyl acetate
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-af2dc1de901f4625a04ec7ca41d62b61
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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