Hydrochloric Acid → (3,5-Dibromo-4-methoxy-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

HRID 1943667Notes

Reaction equation

HRID 1943667 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:5]2[O:6][CH2:7][CH2:8][NH:9][C:4]=2[CH:3]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([Br:24])[C:21]=1[O:22][CH3:23])[C:16](Cl)=[O:17].C(N(CC)CC)C.Cl>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([C:16]([N:9]2[CH2:8][CH2:7][O:6][C:5]3[N:10]=[CH:11][C:2]([CH3:1])=[CH:3][C:4]2=3)=[O:17])[CH:19]=[C:20]([Br:24])[C:21]=1[O:22][CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 235576307-methyl-1H,2H,3H-pyrido[2,3-b][1,4]oxazineHCID 337796303,5-Dibromo-4-methoxybenzoyl chloride

Product 1

HCID 44608222(3,5-Dibromo-4-methoxy-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanoneYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 7-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (79 mg, 0.52 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (259 mg, 0.79 mmol) were dissolved in dichloromethane (2 ml). Triethylamine (0.22 ml, 1.58 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 methanol:dichloromethane=1:30. The fractions containing the product were collected and evaporated to obtain white solid (210 mg, 90%).

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 methanol
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-1767991662b947719c8c82fbf9efadcb
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

Loading…