3-Pyrroline → 1-Cyclopropyl-7-(2,5-dihydro-pyrrol-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

HRID 600734Notes

Reaction equation

HRID 600734 reaction equation
[NH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1.[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:22])=[C:16](F)[C:17]=3[O:19][CH3:20])[C:12](=[O:23])[C:11]([C:24]([OH:26])=[O:25])=[CH:10]2)[CH2:8][CH2:7]1>CN(C=O)C>[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:22])=[C:16]([N:1]4[CH2:5][CH:4]=[CH:3][CH2:2]4)[C:17]=3[O:19][CH3:20])[C:12](=[O:23])[C:11]([C:24]([OH:26])=[O:25])=[CH:10]2)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 660593-PyrrolineHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 575555521-Cyclopropyl-7-(2,5-dihydro-pyrrol-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Pyrroline (1 g; 14.5 mmol) and acid 52 (2.1 g; 7.2 mmol) in DMF (10 mL) were heated at 100° C. overnight. After cooling, the reaction mixture was filtered and washed with water. Acid 119 was isolated.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-1da1e17941e34c4a9e432bb6fbb527e6
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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