Hydrochloric Acid → HCID 66936878, compound

HRID 1943641Notes

Reaction equation

HRID 1943641 reaction equation
[CH:1]1([C:4]2[CH:13]=[N:12][C:7]3[O:8][CH2:9][CH2:10][NH:11][C:6]=3[CH:5]=2)[CH2:3][CH2:2]1.[Br:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([Br:26])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19].C(N(CC)CC)C.Cl>ClCCl>[CH:1]1([C:4]2[CH:13]=[N:12][C:7]3[O:8][CH2:9][CH2:10][N:11]([C:18]([C:17]4[CH:21]=[C:22]([Br:26])[C:23]([O:24][CH3:25])=[C:15]([Br:14])[CH:16]=4)=[O:19])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 66936396HCID 66936396, compound

Product 1

HCID 66936878HCID 66936878, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 ml flask, 7-cyclopropyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (10 mg, 0.057 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (28 mg, 0.085 mmol) were dissolved in dichloromethane (1.2 ml). After cooling to 0□, triethylamine (0.04 ml, 0.285 mmol) was added thereto and then stirred at room temperature for 3 hours. The reaction mixture was neutralized with 1N hydrochloric acid solution and extracted with dichloromethane, and then the combined organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of ethyl acetate and n-hexane (1:1). The fractions containing the product were collected and evaporated to obtain the target compound as white solid (9.0 mg, 33%).

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica eluting with a solvent of ethyl acetate and n-hexane (1:1)
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Sources & evidence

ORD record
ord-de528e176e834ae8b5b684388942ecd8
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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