Hydrochloric Acid → HCID 44608230, compound

HRID 1943677Notes

Reaction equation

HRID 1943677 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([N:12]2[CH2:17][CH2:16][O:15][C:14]3[CH:18]=[N:19][CH:20]=[CH:21][C:13]2=3)=[O:11])[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br.C(=O)([O-])O.[Na+].Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([N:12]2[CH2:17][CH2:16][O:15][C:14]3[CH:18]=[N:19][CH:20]=[CH:21][C:13]2=3)=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 66936690HCID 66936690, compound

Product 1

HCID 44608230HCID 44608230, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 10 ml flask, (3-chloro-4-methoxy-phenyl)-(2,3-dihydro-pyrido[3,4-b][1,4]oxazin-1-yl)-methanone (134 mg, 0.441 mmol) was dissolved in dichloromethane (5 ml), and the mixture was cooled to 0□. 1.0M Boron tribromide dissolved in dichloromethane (2.2 ml, 2.2 mmol) was added thereto and stirred at room temperature for 16 hours. After neutralizing with saturated solution of sodium hydrogen carbonate to pH 8 to 9, the mixture was adjusted to pH 6 again by using 1N hydrochloric acid and extracted with dichloromethane. The combined organic layer was washed with saturated saline solution and 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=1:20. The fractions containing the product were collected and evaporated to obtain the target compound 34 as white solid (65 mg, 50.9%).

Workup

  1. temperaturethe mixture was cooled to 0□
  2. additionwas added
  3. extractionextracted with dichloromethane
  4. washThe combined organic layer was washed with saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica eluting with a solvent of methanol
  9. additionThe fractions containing the product
  10. customwere collected
  11. customevaporated

Sources & evidence

ORD record
ord-71acb73769dc4975aa46b3be2fbb33aa
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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