1-Methylpyrrolidine → HCID 68439913, compound

HRID 2235040Notes

Reaction equation

HRID 2235040 reaction equation
Cl.Cl.[CH:3]([NH:6][CH:7]1[CH2:10][NH:9][CH2:8]1)([CH3:5])[CH3:4].[NH2:11][C:12]1[N:17]=[C:16]([N:18]2[C:27]3[C:22](=[CH:23][C:24]([F:30])=[C:25](F)[C:26]=3[Br:28])[C:21](=[O:31])[C:20]([C:32]([OH:34])=[O:33])=[CH:19]2)[C:15]([F:35])=[CH:14][C:13]=1[F:36].CN1CCCC1.[Cl-].[Li+]>C(OCC)C.CS(C)=O>[NH2:11][C:12]1[N:17]=[C:16]([N:18]2[C:27]3[C:22](=[CH:23][C:24]([F:30])=[C:25]([N:9]4[CH2:10][CH:7]([NH:6][CH:3]([CH3:5])[CH3:4])[CH2:8]4)[C:26]=3[Br:28])[C:21](=[O:31])[C:20]([C:32]([OH:34])=[O:33])=[CH:19]2)[C:15]([F:35])=[CH:14][C:13]=1[F:36]

Participants

7

Reactant 4

HCID 84541-MethylpyrrolidineHCID 433294Lithium ChlorideHCID 154869771-(6-Amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 53439424N-(Propan-2-yl)azetidin-3-amine--hydrogen chloride (1/2)

Product 1

HCID 68439913HCID 68439913, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

N-isopropylazetidin-3-ylamine dihydrochloride (374 mg), 1-(6-amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinolin-3-carboxylic acid (518 mg), N-methylpyrrolidine (0.8 mL), lithium chloride (500 mg) and dimethyl sulfoxide (1.5 mL) were mixed, and the mixture was stirred at 50° C. for 4.5 hours. After the mixture had been left to cool, diethyl ether (10 mL) was added to the mixture and stirred, followed by removing the supernatant. The same procedure was repeated three times. Water (3 mL) was added to the residue, and the pH of the mixture was adjusted to 6 by use of aqueous citric acid solution. The formed solid was collected through filtration, washed three times with water (3 mL), then suspended in ethanol (10 mL), and stirred under heating. The formed solid was collected through filtration, and suspended in diisopropyl ether (10 mL), followed by stirring under heating. The heated suspension was filtrated to yield 410 mg of the title compound.

Workup

  1. waitAfter the mixture had been left
  2. temperatureto cool
  3. stirringstirred
  4. customby removing the supernatant
  5. additionWater (3 mL) was added to the residue
  6. filtrationThe formed solid was collected through filtration
  7. washwashed three times with water (3 mL)
  8. stirringstirred
  9. temperatureunder heating
  10. filtrationThe formed solid was collected through filtration
  11. stirringby stirring
  12. temperatureunder heating
  13. filtrationThe heated suspension was filtrated

Sources & evidence

ORD record
ord-52d1a787340c40adbfe86f3846b88daf
Source dataset
uspto-grants-2010_05
Patent number
US07713997B2

Reaction notes

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