Water → HCID 86664662, compound

HRID 1917433Notes

Reaction equation

HRID 1917433 reaction equation
[NH2:1][C:2]12[CH2:10][N:9]([C:11]3[C:20]([O:21][CH3:22])=[C:19]4[C:14]([C:15](=[O:30])[C:16]([C:27]([OH:29])=[O:28])=[CH:17][N:18]4[C@@H:23]4[CH2:25][C@@H:24]4[F:26])=[CH:13][C:12]=3[F:31])[CH2:8][C:7]31[CH:5]([CH2:6]3)[CH2:4][CH2:3]2.[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].O>C(O)C>[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[NH2:1][C:2]12[CH2:10][N:9]([C:11]3[C:20]([O:21][CH3:22])=[C:19]4[C:14]([C:15](=[O:30])[C:16]([C:27]([OH:29])=[O:28])=[CH:17][N:18]4[C@@H:23]4[CH2:25][C@@H:24]4[F:26])=[CH:13][C:12]=3[F:31])[CH2:8][C:7]31[CH:5]([CH2:6]3)[CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 67490757HCID 67490757, compound

Product 1

HCID 86664662HCID 86664662, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 7-[6-amino-8-azatricyclo[4.3.0.01,3]nonan-8-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (2.24 g, 4.82 mmol) in ethanol (48.2 ml) was added methanesulfonic acid (0.316 ml, 4.87 mmol) and the mixture was stirred at room temperature for 15 hours. To this reaction solution was added water (5 ml) and the mixture was concentrated under reduced pressure. To this residue was added 2-propanol (20 ml) and the mixture was stirred at room temperature for 15 hours. The precipitated solids were collected by filtration. The solids were washed with an excess amount of 2-propanol to afford the title compound 2.41 g (95%) as pale yellow solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionTo this residue was added 2-propanol (20 ml)
  3. stirringthe mixture was stirred at room temperature for 15 hours
  4. filtrationThe precipitated solids were collected by filtration
  5. washThe solids were washed with an excess amount of 2-propanol

Sources & evidence

ORD record
ord-03e8259b95394b26bf61147e6b5ae553
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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