7-[3-(Aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid → 3-Quinolinecarboxylic acid,7-[3-(aminomethyl)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-

HRID 2249258Notes

Reaction equation

HRID 2249258 reaction equation
[CH3:1][O-:2].[Na+].[Na].[NH2:5][CH2:6][CH:7]1[CH2:11][CH2:10][N:9]([C:12]2[C:21](F)=[C:20]3[C:15]([C:16](=[O:29])[C:17]([C:26]([OH:28])=[O:27])=[CH:18][N:19]3[CH:23]3[CH2:25][CH2:24]3)=[CH:14][C:13]=2[F:30])[CH2:8]1>CO>[NH2:5][CH2:6][CH:7]1[CH2:11][CH2:10][N:9]([C:12]2[C:21]([O:2][CH3:1])=[C:20]3[C:15]([C:16](=[O:29])[C:17]([C:26]([OH:28])=[O:27])=[CH:18][N:19]3[CH:23]3[CH2:25][CH2:24]3)=[CH:14][C:13]=2[F:30])[CH2:8]1

Participants

5

Reactant 3

HCID 4695537-[3-(Aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-quinoline-3-carboxylic acidHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 104295303-Quinolinecarboxylic acid,7-[3-(aminomethyl)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide prepare from sodium (0.2 g) and absolute methanol (9 ml) was added 7-(3-aminomethyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g) and the mixture in sealed tube was stirred for 86 hours at 140° to 150° C. and then concentrated. Small amount of water was added to the residue, and the solution was adjusted pH 7 with acetic acid and then concentrated. The resulting residue was purified by silica gel column chromatography eluting with chloroform-methanol-concentrated aqueous ammonia (20:6:1) and recrystallized from methanol to give the title compound (40 mg) as pale yellow prisms, mp 225°-228.5° C. (decompd.).

Workup

  1. concentrationconcentrated
  2. additionSmall amount of water was added to the residue
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel column chromatography
  5. washeluting with chloroform-methanol-concentrated aqueous ammonia (20:6:1)
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-21ca84900863443ca4186ffc12a4b4f3
Source dataset
uspto-grants-1991_08
Patent number
US05043450

Reaction notes

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