Hydrochloric Acid → HCID 44609192, compound

HRID 1943742Notes

Reaction equation

HRID 1943742 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]([C:23]4[CH:31]=[CH:30][CH:29]=[C:28]5[C:24]=4[CH:25]=[CH:26][NH:27]5)=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[O:8]C.[Br-].[Li+].N1CCNCC1.Cl>CN(C)C=O.O>[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]([C:23]4[CH:31]=[CH:30][CH:29]=[C:28]5[C:24]=4[CH:25]=[CH:26][NH:27]5)=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[OH:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4837PiperazineHCID 82050Lithium BromideHCID 66936666HCID 66936666, compound

Product 1

HCID 44609192HCID 44609192, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a 10 ml flask, (3,5-dibromo-4-methoxy-phenyl)-[7-(1H-indol-4-yl)-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl]-methanone (124 mg, 0.23 mmol), lithium bromide (246 mg, 2.83 mmol) and piperazine (29 mg, 0.34 mmol) were dissolved in 5 ml of N,N-dimethyl formamide (DMF), and then stirred at 100° C. for 2 hours. After completion of the reaction by adding water dropwise, the mixture was adjusted to weak acidic condition (pH=6) with 1N hydrochloric acid. The formed solid was filtered and washed with distilled water. The resulting solid was recrystallized from methanol to obtain the target compound 70, i.e., (3,5-dibromo-4-hydroxy-phenyl)-[7-(1H-indol-4-yl)-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl]-methanone (77 mg, 64%).

Workup

  1. customAfter completion of the reaction
  2. filtrationThe formed solid was filtered
  3. washwashed with distilled water
  4. customThe resulting solid was recrystallized from methanol

Sources & evidence

ORD record
ord-8092cc77c314464095e7883f801a8e68
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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