Hydrochloric Acid → 1-{4-[1-(3,5-dibromo-4-hydroxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-phenyl}-ethanone

HRID 1943736Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([Br:31])[C:28]=1[O:29]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:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=3)=[CH:16][C:8]1=2)=[O:6].[Br-].[Li+].N1CCNCC1.Cl>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([Br:31])[C:28]=1[OH:29])[C:5]([N:7]1[CH2:12][CH2:11][O:10][C:9]2[N:13]=[CH:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=3)=[CH:16][C:8]1=2)=[O:6]

Participants

Conditions

Temperature: 100 °C

Procedure

In a 10 ml flask, 1-{4-[1-(3,5-dibromo-4-methoxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-phenyl}-ethanone (119 mg, 0.22 mmol), lithium bromide (189 mg, 2.2 mmol) and piperazine (28 mg, 0.33 mmol) were dissolved in 3 ml of N,N-dimethyl formamide, and then stirred at 100° C. for 2.5 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 67, i.e., 1-{4-[1-(3,5-dibromo-4-hydroxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-phenyl}-ethanone (65 mg, 56%).

Workup

customAfter completion of the reaction
filtrationThe formed solid was filtered
washwashed with distilled water
customThe resulting solid was recrystallized from methanol

Sources & evidence

ORD record: ord-216b9af02b0b4c3ab45c88c36878dac0
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394792B2

Reaction notes

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