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

HRID 1943668Notes

Reaction equation

HRID 1943668 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[N:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[O:8]C.[Br-].[Li+].N1CCNCC1.C(=O)([O-])O.[Na+].Cl>CN(C)C=O>[Br:10][C:6]1[CH:5]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[N:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:14]2=3)=[O:12])[CH:3]=[C:2]([Br:1])[C:7]=1[OH:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 82050Lithium Bromide3×HCID 516892Sodium BicarbonateHCID 44608222(3,5-Dibromo-4-methoxy-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

Product 1

HCID 44608223(3,5-Dibromo-4-hydroxy-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanoneYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 5 ml flask, (3,5-dibromo-4-methoxy-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone (100 mg, 0.23 mmol), lithium bromide (39 mg, 0.45 mmol), piperazine (30 mg, 0.35 mmol) and N,N-dimethyl formamide (1 ml) were added and then stirred at 100□ for 30 minutes. Lithium bromide (39 mg, 0.45 mmol) was further added thereto and then stirred at 1000 for 1 hour. Lithium bromide (39 mg, 0.45 mmol) was further added thereto and then stirred for 1 hour. 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. The formed solid was filtered. The resulting solid 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 the target compound 27-2 as white solid (74 mg, 76%).

Workup

  1. stirringstirred at 1000 for 1 hour
  2. stirringstirred for 1 hour
  3. filtrationThe formed solid was filtered
  4. customThe resulting solid was purified by column chromatography on silica eluting with a solvent of methanol
  5. additionThe fractions containing the product
  6. customwere collected
  7. customevaporated

Sources & evidence

ORD record
ord-ad62dd5e78454f2cbb483e33842a3c83
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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