Water → HCID 44608067, compound

HRID 1943659Notes

Reaction equation

HRID 1943659 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[N:11][C:6]2[O:7][CH2:8][CH2:9][NH:10][C:5]=2[CH:4]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([Br:27])[C:24]=1[O:25][CH3:26])[C:19](Cl)=[O:20].C(N(CC)CC)C.O>ClCCl>[Br:15][C:16]1[CH:17]=[C:18]([C:19]([N:10]2[CH2:9][CH2:8][O:7][C:6]3[N:11]=[CH:12][C:3]([C:2]([F:13])([F:1])[F:14])=[CH:4][C:5]2=3)=[O:20])[CH:22]=[C:23]([Br:27])[C:24]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 669366917-Trifluoromethyl-2,3-dihydro-1H-pyrido[2,3-B][1,4]oxazine

Product 1

HCID 44608067HCID 44608067, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 5 ml flask, 7-trifluoromethyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (27 mg, 0.23 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (65 mg, 0.20 mmol) were dissolved in dichloromethane (0.6 ml), and then triethylamine (0.55 ml, 0.33 mmol) was added thereto dropwise at 0□. After stirring for 4 hours at room temperature, water was added and the mixture was extracted with ethyl acetate. 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=1:100. The fractions containing the product were collected and evaporated to obtain white solid (64 mg, 98%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  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-35914bf01d7b47eb9e6e2d6f3352906a
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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