Water → HCID 44608706, compound

HRID 1943718Notes

Reaction equation

HRID 1943718 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH2:9][CH2:8][O:7][C:6]=2[N:11]=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.O>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([C:16]([N:10]2[CH2:9][CH2:8][O:7][C:6]3[N:11]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]2=3)=[O:17])[CH:19]=[C:20]([Br:24])[C:21]=1[O:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 668191621198154-80-1

Product 1

HCID 44608706HCID 44608706, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 6-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (110 mg, 0.73 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (240 mg, 0.73 mmol) were dissolved in dichloromethane (5 ml). Triethylamine (0.26 ml, 1.8 mmol) was added thereto and then stirred at room temperature for 1 hour. After completion of the reaction by adding water dropwise, 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 amine silica (NH-silica gel) eluting with a solvent of dichloromethane:methanol=19:1. The fractions containing the product were collected and evaporated to obtain the target compound 58, i.e., (3,5-dibromo-4-methoxy-phenyl)-(6-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone, as white solid (230 mg, 71%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on amine silica (NH-silica gel)
  7. washeluting with a solvent of dichloromethane
  8. additionThe fractions containing the product
  9. customwere collected
  10. customevaporated

Sources & evidence

ORD record
ord-1127fb7c5bf44adca061993fdbbec9a7
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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