Piperazine → 4-[1-(3,5-dibromo-4-hydroxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-benzonitrile

HRID 1943731Notes

Reaction equation

HRID 1943731 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([Br:30])[C:27]=1[O:28]C)[C:5]([N:7]1[CH2:12][CH2:11][O:10][C:9]2[N:13]=[CH:14][C:15]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)=[CH:16][C:8]1=2)=[O:6].[Br-].[Li+].N1CCNCC1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([Br:30])[C:27]=1[OH:28])[C:5]([N:7]1[CH2:12][CH2:11][O:10][C:9]2[N:13]=[CH:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=3)=[CH:16][C:8]1=2)=[O:6]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 82050Lithium BromideHCID 66936516HCID 66936516, compound

Product 1

HCID 446090354-[1-(3,5-dibromo-4-hydroxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the same method as in the step d) of Example 45, 4-[1-(3,5-dibromo-4-methoxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-benzonitrile (116 mg, 0.22 mmol), lithium bromide (76 mg, 0.88 mmol) and piperazine (29 mg, 0.33 mmol) were dissolved in N,N-dimethyl formamide (3 ml) and reacted at 1000 to obtain the target compound 65, i.e., 4-[1-(3,5-dibromo-4-hydroxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-benzonitrile, as white solid (49 mg, 43%).

Workup

  1. customreacted at 1000

Sources & evidence

ORD record
ord-c6957c62d4e74ac5bee75e87acfa451f
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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