7-(3-Amino-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid → 3-Quinolinecarboxylic acid, 1,4-dihydro-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-
Reaction equation
[CH3:1][O-:2].[Na+].[Na].[NH2:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[C:20](F)=[C:19]3[C:14]([C:15](=[O:28])[C:16]([C:25]([OH:27])=[O:26])=[CH:17][N:18]3[CH:22]3[CH2:24][CH2:23]3)=[CH:13][C:12]=2[F:29])[CH2:7]1>CO>[NH2:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]([O:2][CH3:1])=[C:19]3[C:14]([C:15](=[O:28])[C:16]([C:25]([OH:27])=[O:26])=[CH:17][N:18]3[CH:22]3[CH2:23][CH2:24]3)=[CH:13][C:12]=2[F:29])[CH2:7]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of sodium methoxide prepare from sodium (0.2 g) and absolute methanol (10 ml) was added 7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3quinolinecarboxylic acid (0.47 g) and the mixture in sealed tube was stirred for 49 hours at 140° to 150° C. and then concentrated. The residue was purified by silica gel column chromatography eluting with chloroform-methanol-concentrated aqueous ammonia (20:6:1) and recrystallized from a solution of dichloromethanemethanol (1:1) to give the title compound (6 mg) as pale yellow prisms, mp 207.5°-212° C.
Workup
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography
- washeluting with chloroform-methanol-concentrated aqueous ammonia (20:6:1)
- customrecrystallized from a solution of dichloromethanemethanol (1:1)
Sources & evidence
- ORD record
- ord-827909439f724f5d92604f10a87be148
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04980470
Reaction notes
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