Sodium Methoxide → 3-Quinolinecarboxylic acid, 1,4-dihydro-7-(3-amino-1-piperidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-

HRID 729066Notes

Reaction equation

HRID 729066 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[C:17](F)=[C:16]3[C:11]([C:12](=[O:25])[C:13]([C:22]([OH:24])=[O:23])=[CH:14][N:15]3[CH:19]3[CH2:21][CH2:20]3)=[CH:10][C:9]=2[F:26])[CH2:3]1.[CH3:27][O-:28].[Na+]>CS(C)=O>[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[C:17]([O:28][CH3:27])=[C:16]3[C:11]([C:12](=[O:25])[C:13]([C:22]([OH:24])=[O:23])=[CH:14][N:15]3[CH:19]3[CH2:20][CH2:21]3)=[CH:10][C:9]=2[F:26])[CH2:3]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14962342HCID 14962342, compound

Product 1

HCID 1480763-Quinolinecarboxylic acid, 1,4-dihydro-7-(3-amino-1-piperidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.21 g) obtained as described in Example 1(b), sodium methoxide (1.2 g) and dimethylsulfoxide (40 ml) was stirred for 2 hours at 120°-140° C. The reaction mixture was concentrated in vacuum and water was added to the residue. Neutralization of the mixture with 1N hydrochloric acid followed by evaporation of the solvent and purification by silica gel column chromatography (chloroform:methanol:ammonium hydroxide=100:30:5) gave 7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid. The physical properties of this product wereidentical with those of the compound obtained in Example 6.

Workup

  1. customobtained
  2. concentrationThe reaction mixture was concentrated in vacuum and water
  3. additionwas added to the residue
  4. customNeutralization of the mixture with 1N hydrochloric acid followed by evaporation of the solvent and purification by silica gel column chromatography (chloroform:methanol:ammonium hydroxide=100:30:5)

Sources & evidence

ORD record
ord-b6aa3b592df84f318f7a03cf0e74c1ef
Source dataset
uspto-grants-1991_09
Patent number
US05051509

Reaction notes

Loading…