Dimethylformamide → 7-(3-Aminoazetidine-1-yl)-1-(6-amino-5-fluoropyridine-2-yl)-8-bromo-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 610262Notes

Reaction equation

HRID 610262 reaction equation
CN(C)C=O.[NH2:6][C:7]1[N:12]=[C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([F:25])=[C:20](F)[C:21]=3[Br:23])[C:16](=[O:26])[C:15]([C:27]([OH:29])=[O:28])=[CH:14]2)[CH:10]=[CH:9][C:8]=1[F:30].Cl.Cl.[NH2:33][CH:34]1[CH2:37][NH:36][CH2:35]1.CN1CCCC1>C(O)C>[NH2:33][CH:34]1[CH2:37][N:36]([C:20]2[C:21]([Br:23])=[C:22]3[C:17]([C:16](=[O:26])[C:15]([C:27]([OH:29])=[O:28])=[CH:14][N:13]3[C:11]3[CH:10]=[CH:9][C:8]([F:30])=[C:7]([NH2:6])[N:12]=3)=[CH:18][C:19]=2[F:25])[CH2:35]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 84541-MethylpyrrolidineHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)HCID 221212461-(6-Amino-5-fluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 221212727-(3-Aminoazetidine-1-yl)-1-(6-amino-5-fluoropyridine-2-yl)-8-bromo-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 75.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To 250 mg of N,N-dimethylformamide were added 80 mg of 1-(6-amino-5-fluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 55 mg of 3-aminoazetidine dihydrochloride, and 150 mg of N-methylpyrrolidine, and the mixture was stirred at 90° C. for 10 minutes. After adding 0.3 ml of ethanol, the solution was allowed to cool, and the precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 68 mg of the title compound as a colorless powder.

Workup

  1. temperatureto cool
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-b07c10898d5c47e0889ee06693f596aa
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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