Dimethylformamide → HCID 23284655, compound

HRID 369209Notes

Reaction equation

[Br:1][C:2]1[C:3](F)=[C:4]([F:34])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[C:16]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:15]([F:26])=[CH:14][C:13]=1[F:27])[CH:9]=[C:8]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:7]2=[O:33].[N-:36]=[N+:37]=[N-:38].[Na+].CN(C)C=O>C(OCC)(=O)C>[N:36]([C:3]1[C:2]([Br:1])=[C:11]2[C:6]([C:7](=[O:33])[C:8]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:9][N:10]2[C:12]2[CH:17]=[C:16]([NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[C:15]([F:26])=[CH:14][C:13]=2[F:27])=[CH:5][C:4]=1[F:34])=[N+:37]=[N-:38]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 8-bromo-1-(5-tert-butoxycarbonylamino-2,4-difluorophenyl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (1,000 mg) and sodium azide (180 mg) were added to N,N-dimethylformamide (20 ml), and the mixture was stirred overnight at 60° C. After the reaction mixture was cooled back to room temperature, ethyl acetate (100 ml) was added to the reaction mixture, and the resultant mixture was washed 3 times with water (100 ml). After an organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain the title compound (428 mg) as an amorphous substance.

Workup

temperatureAfter the reaction mixture was cooled back to room temperature
washthe resultant mixture was washed 3 times with water (100 ml)
dry with materialAfter an organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-4419eeb8aa3b4f08b7b9a88b80042344
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136823

Reaction notes

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