Dimethyl Sulfoxide → 7-(3-Aminoazetidine-1-yl)-1-(5-amino-6-chloropyridine-3-yl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 368425Notes

Reaction equation

HRID 368425 reaction equation
CS(C)=O.Cl.Cl.[NH2:7][CH:8]1[CH2:11][NH:10][CH2:9]1.[NH2:12][C:13]1[CH:14]=[C:15]([N:20]2[C:29]3[C:24](=[CH:25][C:26]([F:32])=[C:27](F)[C:28]=3[Cl:30])[C:23](=[O:33])[C:22]([C:34]([OH:36])=[O:35])=[CH:21]2)[CH:16]=[N:17][C:18]=1[Cl:19]>C(N(CC)CC)C>[NH2:7][CH:8]1[CH2:11][N:10]([C:27]2[C:28]([Cl:30])=[C:29]3[C:24]([C:23](=[O:33])[C:22]([C:34]([OH:36])=[O:35])=[CH:21][N:20]3[C:15]3[CH:16]=[N:17][C:18]([Cl:19])=[C:13]([NH2:12])[CH:14]=3)=[CH:25][C:26]=2[F:32])[CH2:9]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)HCID 221212811-(5-Amino-6-chloropyridin-3-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 221211737-(3-Aminoazetidine-1-yl)-1-(5-amino-6-chloropyridine-3-yl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 49.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To dimethylsulfoxide solution 1 ml of 53 mg of 3-aminoazetidine dihydrochloride and 146 mg of triethylamine at 80° C. was added 80 mg of 1-(5-amino-6-chloropyridine-3-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid with stirring, and the mixture was stirred at 80° C. for 1 hour. The reaction solution was allowed to cool and decanted with diethylether. Ethanol was added to the residue to disperse the solid content, and the solid content was collected by filtration, washed with ethanol, and dried to obtain 45 mg of the title compound as a pale yellow powder.

Workup

  1. stirringthe mixture was stirred at 80° C. for 1 hour
  2. temperatureto cool
  3. customdecanted with diethylether
  4. additionEthanol was added to the residue
  5. additionto disperse the solid content
  6. filtrationthe solid content was collected by filtration
  7. washwashed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-396b9cdc4d974b729986c7af4202d3ea
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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