Methanesulfonic Acid → HCID 11443403, compound

HRID 1865287Notes

Reaction equation

HRID 1865287 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:16]4[CH2:21][CH2:20][CH:19]([NH2:22])[C:18]([CH3:24])([CH3:23])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>C(O)(C)C>[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:16]4[CH2:21][CH2:20][CH:19]([NH2:22])[C:18]([CH3:24])([CH3:23])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 9801295HCID 9801295, compound

Product 1

HCID 11443403HCID 11443403, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

6.50 Grams (16.13 mol) of 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(4-amino-3,3-dimethyl-1-piperidinyl)-4-oxo-quinoline-3-carboxylic acid were suspended in 65 ml of isopropyl alcohol. The suspension was heated to 70-80° C. under stirring and then 1.90 g (19.79 mol) methanesulfonic acid was added. The reaction mixture was heated at reflux for 30 minutes. It was cooled to 30-35° C. and filtered. The solid was washed with 10 ml isopropyl alcohol and dried for 16 hrs in oven under vacuum at 50° C. to give 6.80 g (84%) titled compound, mp 286-290° C.,

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 30 minutes
  3. temperatureIt was cooled to 30-35° C.
  4. filtrationfiltered
  5. washThe solid was washed with 10 ml isopropyl alcohol
  6. customdried for 16 hrs in oven under vacuum at 50° C.

Sources & evidence

ORD record
ord-8b38c3328e294a968580cdb988398b20
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

Loading…