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

HRID 1943660Notes

Reaction equation

HRID 1943660 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]([F:26])([F:25])[F:24])=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[O:8]C.[Br-].[Li+].N1CCNCC1>CN(C)C=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]([F:24])([F:26])[F:25])=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 82050Lithium BromideHCID 44608067HCID 44608067, compound

Product 1

HCID 44608068(3,5-Dibromo-4-hydroxy-phenyl)-(7-trifluoromethyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanoneYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 5 ml flask, (3,5-dibromo-4-methoxy-phenyl)-(7-trifluoromethyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone (30 mg, 0.061 mmol) was dissolved in N,N-dimethyl formamide (0.3 ml), and then lithium bromide (10 mg, 0.12 mmol) and piperazine (7.8 mg, 0.091 mmol) were added thereto. After stirring for 1 hour, the solvent was removed by evaporation under reduced pressure. The residue was neutralized with water and 1N hydrochloric acid. The resulting solid was filtered to obtain the target compound 22-2 as white solid (25 mg, 86%).

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-83b42c513f2a422c9f1b9d2161306eef
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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