Diisopropyl Ether → Diisopropyl Ether

HRID 1415941Notes

Reaction equation

HRID 1415941 reaction equation
[NH2:1][C:2]1[C:3]([F:30])=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:25])=[C:16]([N:19]4[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20]4)[N:17]=3)[C:12](=[O:26])[C:11]([C:27]([OH:29])=[O:28])=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].O.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([OH:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1.[CH:43]([O:46][CH:47]([CH3:49])[CH3:48])([CH3:45])[CH3:44]>CN(C)C=O>[CH:43]([O:46][CH:47]([CH3:49])[CH3:48])([CH3:45])[CH3:44].[C:32]1([CH3:42])[CH:33]=[CH:34][C:35]([S:38]([OH:41])(=[O:39])=[O:40])=[CH:36][CH:37]=1.[NH2:1][C:2]1[C:3]([F:30])=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:25])=[C:16]([N:19]4[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20]4)[N:17]=3)[C:12](=[O:26])[C:11]([C:27]([OH:29])=[O:28])=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 11080272HCID 11080272, compound

Product 2

HCID 7914Diisopropyl EtherHCID 86754099HCID 86754099, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 300 mg of N,N-dimethylformamide were added 100 mg of 1-(3-amino-2,4-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid and 55 mg of p-toluenesulfonic acid hydrate. The mixture was stirred for about 5 minutes. The homogenized solution was combined with 8 ml of diisopropyl ether, stirred, and allowed to stand. The supernatant was removed by decantation. The remainder was combined with 1 ml of ethanol, heated at reflux for 2 minutes, and allowed to cool down. The precipitate was collected by filtration and washed with ethanol and then with diisopropyl ether to give 120 mg of the title compound.

Workup

  1. stirringstirred
  2. customThe supernatant was removed by decantation
  3. temperatureheated
  4. temperatureat reflux for 2 minutes
  5. temperatureto cool down
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-dc80d3126c4a421ea6fe959846800ad4
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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