Dimethyl Sulfoxide → 7-(3-Aminoazetidin-1-yl)-1-(4-amino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 368422Notes

Reaction equation

HRID 368422 reaction equation
CS(C)=O.Cl.Cl.[NH2:7][CH:8]1[CH2:11][NH:10][CH2:9]1.[NH2:12][C:13]1[C:18]([F:19])=[C:17]([F:20])[N:16]=[C:15]([N:21]2[C:30]3[C:25](=[CH:26][C:27]([F:33])=[C:28](F)[C:29]=3[Cl:31])[C:24](=[O:34])[C:23]([C:35]([OH:37])=[O:36])=[CH:22]2)[C:14]=1[F:38]>C(N(CC)CC)C>[NH2:7][CH:8]1[CH2:11][N:10]([C:28]2[C:29]([Cl:31])=[C:30]3[C:25]([C:24](=[O:34])[C:23]([C:35]([OH:37])=[O:36])=[CH:22][N:21]3[C:15]3[C:14]([F:38])=[C:13]([NH2:12])[C:18]([F:19])=[C:17]([F:20])[N:16]=3)=[CH:26][C:27]=2[F:33])[CH2:9]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)HCID 221212331-(4-Amino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 221211907-(3-Aminoazetidin-1-yl)-1-(4-amino-3,5,6-trifluoropyridin-2-yl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 50.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 1 ml dimethylsulfoxide solution of 70 mg of 3-aminoazetidine dihydrochloride and 250 mg of triethylamine at 80° C. was added 150 mg of 1-(4-amino-3,5,6-trifluoropyridine-2-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 85 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-07d82dd8206a434a9c3443e1f4a01bcb
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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