Piperazine → 1-(3,5-dibromo-4-hydroxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-carbonitrile
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([Br:24])[C:21]=1[O:22]C)[C:5]([N:7]1[CH2:12][CH2:11][O:10][C:9]2[N:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:8]1=2)=[O:6].[Br-].[Li+].N1CCNCC1>>[Br:24][C:20]1[CH:19]=[C:4]([CH:3]=[C:2]([Br:1])[C:21]=1[OH:22])[C:5]([N:7]1[CH2:12][CH2:11][O:10][C:9]2[N:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:8]1=2)=[O:6]Participants
4
Procedure
By the same method as in the step f) of Example 22, 1-(3,5-dibromo-4-methoxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-carbonitrile (12 mg, 0.026 mmol) was reacted with lithium bromide (LiBr) (4.62 mg, 0.053 mmol) and piperazine (3.4 mg, 0.0399 mmol) to obtain the target compound 47-2, i.e., 1-(3,5-dibromo-4-hydroxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-carbonitrile as white solid (9 mg, 78%).
Sources & evidence
- ORD record
- ord-8664d65867994b068521633ee803170a
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394792B2
Reaction notes
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